Large group vacation rentals in Bridgewater, VT

Escape the noise and settle into a peaceful country retreat designed for rest, creativity, and renewal. Situated within a beautifully restored barn, which dates to 1780, this thoughtfully renovated 1-bedroom, 1-bath spacious apartment comfortably accommodates up to 2 guests and is surrounded by nature in a serene, Zen-inspired setting. It’s an ideal escape for artists, writers, remote workers, yogis, or anyone seeking a slower pace. Whether you’re planning a weekend getaway or an extended stay, this is the perfect place to relax and unwind. Spend your mornings watching wildlife, your afternoons exploring the property’s wooded walking trails, and your evenings enjoying the quiet beauty of the countryside. During the winter months, the 44 acre property, half open and half wooded, is perfect for cross-country skiing and snowshoeing. Whether you’re taking a leisurely walk through the woods, painting, writing, practicing yoga, or simply unwinding with a good book, the peaceful natural surroundings provide endless inspiration. Lovingly renovated with reclaimed materials and distinctive vintage touches, this unique barn apartment blends rustic charm with modern comfort, creating a warm and inviting space to relax and enjoy during your stay Although you’ll feel worlds away from the hustle and bustle, the property is conveniently located just minutes from downtown Woodstock where you’ll find local shops, restaurants, and everyday conveniences before returning to the tranquility of your private retreat. Perfect for couples or solo travelers, this home is best suited for guests seeking peace, nature, and relaxation. It’s a place to slow down, reconnect, and appreciate the simple beauty of the countryside. For those exploring further afield, it is a short drive to all that central Vermont offers. Things to Know - The homeowners live across the street from the property, but you’ll still enjoy complete privacy during your stay. - There is no smoking or vaping inside or on the grounds of this home Vermont Meals and Room Tax Number: MRT-11472019

Set back off the road, this charming two bedroom ranch home offers a little bit of everything with over 11 acres just over the Woodstock Village line. Please see: Other Things to Note For Area Details, please see: The Neighborhood & Getting Around • Pet-Friendly, fee applies. Woodstock Way, Home Features: • 2 Bedrooms, 1 Bath, up to 6 guests • Cozy Fireplace in Living Room • 11-acre Property with Trails! • Free WiFi & Smart TV • Pack ’n play and/or high chair may be available upon request (subject to availability) Experience the rare opportunity to stay in a serene, 11-acre property located just beyond the Woodstock Village line. This charming two-bedroom ranch offers a unique blend of comfort and nature, making it an ideal getaway for those seeking tranquility and adventure. With two well-sized bedrooms and a full bathroom, the space is perfect for a cozy retreat. The open floor plan features beautiful wood floors throughout. The fabulous kitchen is outfitted with all stainless steel appliances, featuring a Forno commercial fridge and a Zline 6-burner range with griddle and dual ovens, perfect for culinary enthusiasts. An island separates the kitchen from the living room, which opens to an enclosed front porch, perfect for morning coffee or evening relaxation. A spacious family room and main floor laundry add convenience and comfort. Enjoy the open front lawn with mature trees and a winding driveway. Explore several acres of land with potential trails leading to the crest of the hill. Set back off the road, this property provides a peaceful escape with plenty of space to explore. Whether you’re seeking a primary residence or a second home, this charming ranch offers flexibility and potential for personalization. Enjoy the best of both worlds with a secluded property just minutes from the heart of Woodstock. Parking is convenient with a detached garage and driveway, accommodating up to three vehicles. The property’s location is ideal, situated just over a mile from the Village Center, providing easy access to local attractions and amenities. Enjoy stunning views of the surrounding mountains, with a country club and golf course nearby for golf enthusiasts. Explore charming shops and boutiques just a short distance away, and take advantage of skiing opportunities close by for winter sports lovers. This home uses keyless entry for self-check-in; your door code is sent by email and text within two weeks of arrival. Early check-in and late check-out are available upon request (subject to availability). Please contact us at least 24 hours in advance. Come and make unforgettable memories in this charming Vermont haven. We welcome you! This Upper Valley experience seamlessly weaves together the natural beauty of Vermont with the cultural vibrancy of Hanover, creating an unforgettable blend of outdoor adventures, historical exploration, and small-town charm. Whether you’re soaking in the scenic wonders or delving into cultural delights, the Upper Valley promises a journey for every traveler. Discover endless opportunities for adventure and relaxation in the Woodstock-Barnard area of Vermont, where every moment is infused with the essence of New England charm. Nestled amidst breathtaking natural beauty, our vacation rental offers unparalleled access to various attractions and activities that cater to every interest. Traveling to/around the Upper Valley region of Vermont, explore by foot, by ski, by bike, or by horseback: • You’ll definitely need your own car, as there are limited taxis available. While the town itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots. The outer parts of town, such as South Woodstock, are only conveniently accessed by car. • Bike rentals are available in the village, though biking in the commercial area of the village is discouraged, as the flow of people and cars can be concentrated. The terrain has many hills, and a mountain bike should be used to traverse such rugged areas. Airports: • Burlington (BTV) [VT] • Lebanon (LEB) [NH] • Manchester (MHT) [NH] • Boston Logan (BOS) [MA] Popular Landmarks: • Mount Ascutney • Norman Williams Public Library • Woodstock Town Hall • Marsh Billings Rockefeller Historical Site • The New England Falconry • President Calvin Coolidge State Historic Site • Sugarbush Farm • Hanover, home to Dartmouth University Please pay close attention to following the house rules. Non compliance could result in sizable fines. • All guests staying at an Field and Farms Vacation Homes by Portoro are required to sign (esignature) a rental agreement and complete identity registration. • Age restrictions apply. Reservation holder must be 25 years of age. • Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don’t hesitate to reach out to Field and Farm Vacation Homes by Portoro directly. • Known damages incurred during your stay must be reported to the property manager immediately. • Before check in, we will send you detailed directions to ensure a seamless arrival. • Check-in time is 3:00 p.m. Check-out time is 10:00 a.m. • We cannot guarantee early check ins or late checkouts. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night. • Some homes have cameras for external monitoring only. • In the State of Vermont and in the Village of Woodstock, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction. • This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host. • Animals/Pets, Dogs Only, Guidelines and Fee Animals/pets must be disclosed prior to reservation arrival date. Only dogs are permitted in “Pet-Friendly” Property listings. Allowed number of dogs will be expressly stated in the listing and a $150.00 fee per animal/pet is required. Animals/pets are not permitted anywhere on the premises unless prior approval is obtained. Any unauthorized animals/pets at the property will result in a $150.00 per day / per animal/pet fee, and may result in your reservation being canceled, and you may be required to vacate from the Property. • Woodstock Way allows for a maximum of 2 dogs at $150.00 per dog per stay.

Escape to Highland Cabin, a sunlit Woodstock retreat, close to town yet perched on a steep, quiet hillside for extra privacy. Start your morning with a peaceful walk to the Mt. Tom trailhead or enjoy a leisurely 15-minute stroll down into the village and the Woodstock Inn. After exploring, come home to vaulted ceilings, forest views, and a freshly updated, pet-friendly haven that sleeps up to 4 in the heart of Vermont. Please see: Other Things to Note For Area Details, please see: The Neighborhood & Getting Around • Pet Friendly, fee applies per pet. Highland Cabin Home Features: • 1 Bedroom, 1 Bath, up to 4 guests • Stainless Steel Appliances in Updated Kitchen • Remote Work Desk: Monitor & Keyboard • Solar Powered! • Free WiFi & Smart TV • Pack ’n play and/or high chair may be available upon request (subject to availability) Highland Cabin is your cozy, sunlit retreat nestled at the foothills of Mount Peg in charming Woodstock, Vermont, just minutes from the village and perfectly positioned for both relaxation and adventure. Perched on a steep hillside, the cabin offers a peaceful sense of seclusion while still keeping you close to Woodstock’s shops, cafés, and galleries. The Mt. Tom trailhead is also nearby, making outdoor exploration easily accessible. Traveling with a pet? Furry companions are welcome at Highland Cabin! The large open yard and neighborhood trails are perfect for pets to stretch their legs and explore. Please note: there is a pet fee required for each stay, just let us know if you’ll be bringing your four-legged friend. Perfect for couples, small families, or solo travelers seeking romance, relaxation, or a quiet work retreat, this freshly updated pet-friendly one-bedroom cottage blends classic New England character with stylish modern touches. Step inside to warm wood floors and an open living and dining space, with natural light pouring in through oversized windows that frame beautiful forest views. The spacious king bedroom features vaulted ceilings and an Avocado bed, offering a serene place to recharge after a day’s adventure. A sleeper sofa in the living area (with bedding in the corner cabinet) comfortably accommodates two additional guests, bringing total occupancy to four. You’ll also find a spa-like full bathroom with a soaking tub/shower combo and the convenience of an in-unit washer and dryer for longer stays. The welcoming living area offers a comfy sofa, games tucked away in the corner cabinet, and a smart TV on a full-motion mount, perfect for movie nights, game nights, or relaxed downtime. The full kitchen features stainless steel appliances and a beautiful butcher block countertop, ideal for preparing cozy meals at home. Working remotely? A thoughtfully designed workspace awaits, complete with a desk, ergonomic chair, monitor, and keyboard. Positioned across from the cheerful breakfast bar and kitchen, it offers calming forest views while you work or create. Enjoy year-round comfort with reliable heating, fast WiFi, solar power, and hassle-free parking right at the cabin. Begin and end your days in the large enclosed porch, offering a convenient bench and shoe rack for easy gear changes. Two classic red rocking chairs are yours to use, bring them out to the front yard to enjoy fresh Vermont air and peaceful mountain views with your morning coffee or evening glass of wine. In winter, the porch serves as a practical mudroom; in the warmer months, it becomes a tranquil sitting area filled with natural light. Whether you’re skiing at nearby resorts, exploring scenic woodland trails, or simply unwinding in your hillside retreat, Highland Cabin is the perfect base for your Vermont getaway. Experience the beauty, charm, and relaxation that Woodstock has to offer, for you and your furry family members! Let Highland Cabin be your home for your next Vermont escape. Please Note: The property is located on an uphill road. During the winter months, we strongly recommend guests use a four-wheel-drive (4WD) vehicle to ensure safe and reliable access to the property. This home uses keyless entry for self-check-in; your door code is sent by email and text within two weeks of arrival. Early check-in and late check-out are available upon request (subject to availability). Please contact us at least 24 hours in advance. Come and make unforgettable memories in this charming Vermont haven. We welcome you! This Upper Valley experience seamlessly weaves together the natural beauty of Vermont with the cultural vibrancy of Hanover, creating an unforgettable blend of outdoor adventures, historical exploration, and small-town charm. Whether you’re soaking in the scenic wonders or delving into cultural delights, the Upper Valley promises a journey for every traveler. Discover endless opportunities for adventure and relaxation in the Woodstock-Barnard area of Vermont, where every moment is infused with the essence of New England charm. Nestled amidst breathtaking natural beauty, our vacation rental offers unparalleled access to various attractions and activities that cater to every interest. Traveling to/around the Upper Valley region of Vermont: • You’ll definitely need your own car, as there are limited taxis available. While the town itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots. The outer parts of town, such as South Woodstock, are only conveniently accessed by car. Please keep in mind all wheel drive is recommended for the winter months as it is a steep drive to the home as well as other local areas. • Bike rentals are available in the village, though biking in the commercial area of the village is discouraged, as the flow of people and cars can be concentrated. The terrain has many hills, and a mountain bike should be used to traverse such rugged areas. • You can also explore by foot, by ski, or by horseback! Airports: • Burlington (BTV) [VT] • Lebanon (LEB) [NH] • Manchester (MHT) [NH] • Boston Logan (BOS) [MA] Popular Landmarks: • Mount Ascutney • Norman Williams Public Library • Woodstock Town Hall • Marsh Billings Rockefeller National Historical Park • Saint Gaudens National Historic Site • President Calvin Coolidge State Historic Site • Alden Partridge Plaque • Joseph Smith Memorial • Whale’s Dance • Largest Zipper in North America • Vermont Vietnam Veteran’s Memorial • Hanover, Home to Dartmouth University Please pay close attention to following the house rules. Non compliance could result in sizable fines. • All guests staying at an Field and Farm Vacation Homes by Portoro are required to sign (esignature) a rental agreement and complete identity registration. • Age restrictions apply. Reservation holder must be 25 years of age. • Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don’t hesitate to reach out to Field and Farm Vacation Homes by Portoro directly. • Known damages incurred during your stay must be reported to the property manager immediately. • Before check in, we will send you detailed directions to ensure a seamless arrival. • Check-in time is 3:00 p.m. Check-out time is 10:00 a.m. • We cannot guarantee early check ins or late checkouts. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night. • Some homes have cameras for external monitoring only. • Hotel Tax Collection: In the State of Vermont and in Windsor County, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction. • Some homes offer pools/hot tubs, or access to communal pools. There is no guard around the water features when available. Use at your own risk. • This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host. • Animals/Pets: Dogs Only, Guidelines and Fee Animals/pets must be disclosed prior to reservation arrival date. Only dogs are permitted in “Pet-Friendly” Property listings. Allowed number of dogs will be expressly stated in the listing and a $150.00 fee per animal/pet is required. Animals/pets are not permitted anywhere on the premises unless prior approval is obtained. Any unauthorized animals/pets at the property will result in a $150.00 per day / per animal/pet fee, and may result in your reservation being canceled, and you may be required to vacate from the Property. • The property allows for a maximum of 2 dogs at $150.00 per dog per stay.

Trailside Six: Ski-On/Off Condo for 8 with Private Hot Tub & Sauna This is the slopeside ski vacation you have been trying to find. Trailside Six is a true ski-on, ski-off three-bedroom condo that sleeps eight, located directly on Killington’s Great Eastern trail. Forget the parking lots and shuttle buses. Your stay includes boot and glove dryers in the entry, a real wood-burning stove for an authentic "après-ski" feel, and the two key amenities skiers search for: a private hot tub on the deck and a private indoor sauna. Cook Together Eat Better The main level features an open-plan great room that connects the living, dining, and kitchen areas. The kitchen is fully equipped for making real meals, so you can gather the group for a big breakfast before hitting the slopes or a relaxing dinner in front of the fire. The main floor also includes a Queen bedroom and a fully renovated bathroom with a walk-in rainfall shower. Rest For The Whole Group Upstairs, you will find two more bedrooms and a second full bathroom with a double vanity, ensuring there is no wait time in the morning. One bedroom features a full-over-full bunk bed and its own TV, making it a perfect kids’ space. The primary King bedroom includes an additional sofa bed, offering flexible sleeping arrangements for your group. This property is professionally managed by a local team, ensuring your stay is seamless. All-wheel drive or 4-wheel drive with snow tires is recommended for winter access. Dogs are welcome with a pet fee. The hot tub is available year-round (an optional setup fee applies outside of peak ski season). Guests receive exclusive ski and snowboard rental discounts with local Killington partners, plus limited lift ticket deals based on availability. • Ski On/Off: This home is located on the Great Eastern ski trail and offers ski on/off access when the trail is open. Early/late season trail conditions are weather-dependent, and neither the host nor property manager is responsible for these conditions. Reservations cannot be canceled due to weather or lack of snow. For up-to-date trail information, visit the Killington Resort website before booking. Your dates may fall under early/late season rates. • Private Shuttle Services: In partnership with Ski On Ski Off Killington, we provide private shuttle services to the ski lifts and town for an additional fee. Contact us for details. • Rental Agreement: Guests must e-sign and return our written rental agreement. • Hot Tub: The hot tub is included for peak ski season weekends (late December to mid-March). For all other periods, there is an optional $195 setup fee. You understand that use of the hot tub is at your own risk and that special risks may be involved in using the hot tub. You accept full responsibility for any bodily injury arising from use of the hot tub, and hold owner and property manager harmless. • Guest Occupancy: Do not exceed the agreed guest occupancy. Over-occupancy will result in immediate eviction and fines. • Minimum Rental Age: Guests must be 25 years or older to rent this property. • Shoes: Please do not wear shoes inside the house. • Check-In/Out: Smart lock door codes will be provided for contactless check-in and check-out. While we offer some flexibility with check-in and check-out times depending on other bookings, guaranteed early check-in or late check-out may be available for an additional fee. • Smoking Policy: The entire home is non-smoking, including e-cigarettes. Smoking is only permitted outdoors. A $750 fine will be charged for smoking inside the house. • Cameras: For safety and security, there are exterior cameras on the property capable of recording at all times. There are no cameras in any living areas. • Quiet Hours: Quiet hours are from 10 PM to 8 AM. The property may use Minut, a smart home device that monitors noise levels to address disturbances without disrupting your stay. Minut is 100% privacy compliant and required for this property. Please reach out if you have questions. • Fireworks: Fireworks are not permitted at this property. • Parties/Events: Parties and events are not allowed. • Pets: This property is pet friendly with the payment of our non-refundable pet fee per dog. • Winter Weather: Winter weather can be unpredictable. We do not offer refunds due to weather or ski trail conditions and recommend purchasing travel insurance for unforeseen events. All-wheel drive and winter tires are strongly recommended. • Please be advised that this property utilizes a ladder to access the bunk beds. By renting this property, you are agreeing to hold the owner and property manager harmless for any injury or death that is resulting from the use of the ladder. • Limitation of Liability: The owner and their rental agent shall not be held liable for any injuries or damages to the tenant, the tenant’s family, or guests that occur during the tenant’s occupancy of the property. The Tenant agrees to indemnify and hold the property manager and their representatives harmless from any and all claims, liabilities, or legal actions arising from the Tenant’s use or occupancy of the premises.

Welcome to Northeast Passage Chalet – a retreat where rustic Vermont charm meets modern comfort! The Killington golf course and Green Mountain National Golf Course are just a few minutes from this location. Northeast Passage Chalet offers a one-of-a-kind combination of a stunning, natural setting, a cozy ambiance, and numerous amenities to make your vacation getaway truly unique and memorable. Tucked into the woods at the end of a private, wooded road surrounded by nature, you’ll marvel at the privacy and the beauty of its peaceful setting. From the upper deck you’ll enjoy the wonderful mountain views, and from both the upper and lower deck, you’ll peer into the woods and enjoy the trickle of the mountain stream that runs by the house. Strategically placed on the lower deck overlooking the woods and the stream is the large, outdoor hot tub – a gathering place for you and your family and friends to swap stories from your day – great for easing sore muscles and sharing laughs under the stars, or a quiet place to relax and reflect on the wonders of nature. The unmatched peace and privacy and the natural surrounding will take your breath away. And all this is just a few minute’s drive from the brand new, 8 person Killington Skyeship gondola that will whisk you to the mid-station or to the top of Killington! The house is vintage Vermont, with a soaring cathedral ceiling, a large, rustic stone fireplace, and a two story wall of glass facing the mountain view in the cozy main living area on the second floor. The open-concept kitchen, dining area, and main living area all blend together, so the camaraderie of meal prep, dining, or just lingering by the fire can be shared by all. The house also boasts a second living/recreation area on the first floor that adds even more fun, with a large TV, drink fridge, wet bar, and a handcrafted wood counter that’s perfect for snacks, games, or a quick check of your emails. It can be a place for the whole family to hang out, or a separate space for the kids to call their own. Bedrooms and bathrooms are thoughtfully spread out on each of the three levels, sleeping 10, providing privacy, and making it easy for multiple families to stay comfortably. Adults will appreciate the inviting queen bedrooms, and the kids will love their own dedicated bunkroom. To top it off, air conditioning ensures everyone’s comfort even on warmest of summer days. This is a house designed for making memories, whether your gathering by the fire, enjoying nature while soaking in the hot tub, or indulging in game-night in the rec room! ulging in game night in the rec room! • Killington Resort extensive system of mountain biking trails. • Killington Adventure Center – Zip Lines, Mountain Coaster, Free Fall Jump Tower and more • Hiking – Vermont’s Long Trail, Appalachian Trail • Kayaking – Kent Pond, Woodward Reservoir and Chittenden Pond and more • Coolidge Homestead – Vermont’s #1 visited site in Plymouth VT only 10 minutes away • Woodstock VT filled with wonderful shops and art galleries • Marsh Billings Rockefeller National Historical Park in Woodstock VT • Billings Farm Museum – a wonder family activity • Green Mountain Golf Course – the # 1 public course in the state • Killington Golf Course owned by the resort • VINS – Vermont Institute of Natural Science – a rescue and birth sanctuary.

Welcome to BruinsDen, a luxurious ski-on, ski-off rental in Killington, VT. This spacious 4-bedroom retreat offers modern comfort with mountain views, fully stocked kitchen, updated bathrooms, a game room, and an outdoor hot tub. Perfect for families and friends seeking the ultimate alpine escape. Ski on Ski off requires Home Stretch trail to be open - please check with the Killington Resort for trail conditions. Introducing "BruinsDen" - A Luxurious Ski-On, Ski-Off Retreat in Killington, VT Nestled in the heart of Vermont’s pristine winter wonderland, BruinsDen offers an exquisite haven for the discerning traveler seeking the ultimate alpine escape. This stunning rental property sits proudly on the Home Stretch ski trail in Killington, providing an unparalleled ski-in, ski-out experience for guests. With its recent top-to-bottom renovation, BruinsDen effortlessly marries classic mountain charm with modern opulence, offering a lavish home away from home that redefines the art of alpine living. Bedrooms Fit for Royalty: With four well-appointed bedrooms, BruinsDen comfortably accommodates families, friends, or even multiple couples. The master bedroom, a sanctuary of serenity, features a lavish en-suite bathroom and a queen-size bed, ensuring a tranquil night’s sleep. The second bedroom boasts a Full/Full bunk bed, ideal for the kids or those young at heart. A third bedroom is adorned with a luxurious queen-size bed, and the final bedroom provides the perfect retreat for the younger members of your group, offering four twin beds across two bunk beds. Modern Elegance Meets Mountain Comfort: Step into the spacious, open-concept living area where you’ll find a fully stocked gourmet kitchen, a culinary delight waiting to be explored. With top-of-the-line appliances, granite countertops, and ample space, it’s a chef’s dream. Gather around the dining table with loved ones, while taking in the panoramic views through the towering two-story windows. Unwind and Entertain: BruinsDen is not only a retreat for the slopes but also a paradise for relaxation and entertainment. The property features four meticulously updated bathrooms, ensuring both comfort and convenience. For those seeking leisure, a well-appointed living room is perfect for cozy nights in. An office space is available for those who need to attend to business during their stay. And when it’s time to let loose, head to the dedicated game room for a bit of friendly competition. A View That Takes Your Breath Away: The crowning jewel of BruinsDen is its awe-inspiring two-story window that frames a breathtaking panorama of the majestic mountains. Whether you’re sipping morning coffee or enjoying a glass of wine in the living room in the evening, this view will capture your heart and soul, leaving an indelible mark on your memory. Outdoor Serenity: Step outside to the private deck where an inviting outdoor hot tub beckons, offering soothing relaxation under the starlit Vermont sky. Whether you’re soaking in the hot tub or unwinding on the deck, you’ll be captivated by the pristine natural beauty that surrounds you. For those who demand nothing but the best, BruinsDen is the epitome of luxury living in Killington. With its ski-on, ski-off convenience, breathtaking mountain views, and a plethora of modern amenities, this is a rental property that transforms your winter getaway into a truly unforgettable experience. Book your stay at BruinsDen today and elevate your Vermont retreat to new heights. We will send you a door code on the day you check in for access. We are local if you need us.

Welcome to our beautifully renovated Barn located just ten minutes away from the historic town of Woodstock. Enjoy breathtaking views of the valley and the surrounding farm, while indulging in the various amenities we have to offer. Please see: Other Things to Note For Area Details, Please see: The Neighborhood & Getting Around •This is a no pet/animal home. •2027 Winter Seasonal Program, Ask How to Save 35% Please note that this is a working farm. The driveway is shared with the Farm Manager, who happily will show you around! Their living quarters are in a separate barn on the property, across from where you’ll stay. The Barn at Winterfound Farm, Home Features: • 3 Bedrooms, 2 Baths, up to 8 guests • All Bedrooms Feature Large Windows & Views • Chef’s Dream! Well-Equipped Kitchen • Private Covered Hot Tub • Free WiFi & Smart TVs • Pack ’n play and/or high chair may be available upon request (subject to availability) Experience the rhythms of our farm as you observe a variety of animals in their natural setting. You may even spot our on-site farmer tending to the farm! With 3 bedrooms and 2 bathrooms, our farmhouse is perfect for families or groups of friends seeking a serene escape. Take advantage of the miles and miles of VAST trails right outside your doors and past the idyllic pond, perfect for hiking, biking, and exploring the beauty of Vermont. Unwind in our private covered hot tub, perfectly placed to offer stunning views of the farm and valley. Located just a short drive from Quechee, PICO, and Killington Ski Resorts, our property is the perfect base for a winter skiing adventure. We are just minutes away from Saskadena Six. In the summer, enjoy the picturesque beauty of the surrounding farm and the vibrant foliage of autumn. With every modern amenity you could need at hand, our farmhouse offers you a unique opportunity to experience a peaceful countryside getaway like no other. Don’t miss out on the chance to stay in our rustic yet high-end getaway. The moment you step through the double front doors of this stunning open-concept home, you are immediately enveloped by the charming ambiance that only a cozy farmhouse can provide. Boasting two bedrooms on the first level, this home is perfect for families or groups of friends looking to experience the tranquility of Vermont country living. One of the bedrooms features a bunk bed, with a full-size bed on the bottom and a twin-size bed on top. A trundle bed is also available, offering ample sleeping space for up to four guests. The full bathroom on this level includes a shower, while the stackable washer and dryer found between the bathroom and the bunk room make for convenient and practical living. Across the hall from the bathroom, you will find the Queen room, a peaceful and serene retreat for two. All bedrooms feature large windows, revealing spectacular views of the surrounding countryside, allowing guests to immerse themselves in the natural beauty of this idyllic location. At the back of the house lies an inviting sitting room, complete with cozy furnishings and access to a large stone patio overlooking the verdant garden and valley beyond. This is the perfect space to unwind, relax, and take in the breathtaking views of the surrounding landscape. Head upstairs for even more entertainment and relaxation, with a plush King-size bed awaiting you in the primary bedroom. The open-concept space on this level includes a charming living room to your right, with a central woodstove surrounded by plush furnishings. Separating the living space from the gourmet kitchen is the spacious dining area, where a stunning natural wood table seats up to eight guests. The views of the valley from the dining area are spectacular. The kitchen is a chef’s dream, equipped with every appliance and spice needed to create culinary masterpieces for friends and family. Between the primary bedroom and the kitchen, guests will also find the second full bathroom with a deep soaking tub and shower, offering the ultimate in relaxation and pampering. Guests are invited to enjoy the charm of the farm by observing the animals from a distance as they go about their day. And for those looking to soak up the natural beauty of the area, there is a covered hot tub equipped to accommodate up to four people, perfect for enjoying stunning views of the valley while soaking away any and all cares. Bed setup: 1st Floor: Bunk bed with twin over double and trundle bed (sleeps 4), Queen bed (sleeps 2) / 2nd Floor: King bed (sleeps 2) *2027 Winter Seasonal Program (Long-Term Reservations): Looking ahead to ski season? Make Vermont home for the season with Portoro’s 2027 Winter Seasonal Program. It’s the perfect way to enjoy an extended stay near the mountains, cozy up for the season, and experience winter the right way. Designed for guests seeking a seamless extended stay in professionally managed homes across sought-after winter destinations. Plan ahead and save 35%. Reach out now to learn more about seasonal availability and details. *Long Term Reservations: Guests booking reservations lasting 55 nights or more are responsible for and agree to pay all utilities which may include, but are not limited to: Propane, Oil, Electricity, Firewood, Trash Removal, and Snow Removal. These charges will be assessed within 60 days after check-out. Reservations with any dates between 1/4/27 and 3/6/27 must be 55 nights or more. This home uses keyless entry for self-check-in; your door code is sent by email and text within two weeks of arrival. Early check-in and late check-out are available upon request (subject to availability). Please contact us at least 24 hours in advance. Come and make unforgettable memories in this charming Vermont haven. We welcome you! This Upper Valley experience seamlessly weaves together the natural beauty of Vermont with the cultural vibrancy of Hanover, creating an unforgettable blend of outdoor adventures, historical exploration, and small-town charm. Whether you’re soaking in the scenic wonders or delving into cultural delights, the Upper Valley promises a journey for every traveler. Discover endless opportunities for adventure and relaxation in the Woodstock-Barnard area of Vermont, where every moment is infused with the essence of New England charm. Nestled amidst breathtaking natural beauty, our vacation rental offers unparalleled access to various attractions and activities that cater to every interest. Traveling to/around the Upper Valley region of Vermont, explore by foot, by ski, by bike, or by horseback: • You’ll definitely need your own car, as there are limited taxis available. While the town itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots. The outer parts of town, such as South Woodstock, are only conveniently accessed by car. • Bike rentals are available in the village, though biking in the commercial area of the village is discouraged, as the flow of people and cars can be concentrated. The terrain has many hills, and a mountain bike should be used to traverse such rugged areas. Airports: • Burlington (BTV) [VT] • Lebanon (LEB) [NH] • Manchester (MHT) [NH] • Boston Logan (BOS) [MA] Popular Landmarks: • Mount Ascutney • Norman Williams Public Library • Woodstock Town Hall • Marsh Billings Rockefeller Historical Site • The New England Falconry • President Calvin Coolidge State Historic Site • Sugarbush Farm • Hanover, home to Dartmouth University Long Term Reservations: Guests booking reservations lasting 55 nights or more are responsible for and agree to pay all utilities which may include, but are not limited to: Propane, Oil, Electricity, Firewood, Trash Removal, and Snow Removal. These charges will be assessed within 60 days after check-out. Reservations with any dates between 1/4/27 and 3/6/27 must be 55 nights or more. House Rules & Important Information By booking with Field & Farm Vacation Homes by Portoro, guests agree to the guidelines below to help ensure a safe, respectful, and enjoyable stay. • Portoro Rental Agreement + Identity Registration: All guests staying at one of our Portoro homes are required to complete identity registration and sign a rental agreement via e-signature. Non-compliance may result in sizable fines. • Age Requirement: The reservation holder must be 25+. • Arrival Support + House Manual + 24/7 Support: Upon arrival, Portoro aims to ensure your safety, proper access to the home, and understanding of guest features. All guests are required to read the house manual upon arrival. If you have any questions, please reach out to Portoro, our team is available 24/7. • Directions + Check-In Details: Before check-in, Portoro will send all check-in details, detailed directions, and a digital guest guide for the home by email and text to help ensure a seamless arrival. • Check-In / Check-Out (Early/Late Requests): Check-in is 3:00pm and check-out is 10:00am. We can’t guarantee early check-ins or late check-outs, and a fee typically applies. When approved, fees apply for times outside a one-hour window of standard check-in/check-out. If you need significant flexibility, the best option is to book an additional night. • Local Taxes (Including Extended Stays): Vermont and applicable local jurisdictions require lodging operators to collect rooms and meals / lodging-related taxes. These taxes are collected within the booking transaction when required. For stays over 29 days, please inquire separately for terms and conditions. • Long Term Reservations: Guests booking reservations lasting 55 nights or more are responsible for and agree to pay all utilities which may include, but are not limited to: Propane, Oil, Electricity, Firewood, Trash Removal, and Snow Removal. These charges will be assessed within 60 days after check-out. Reservations with any dates between 1/4/27 and 3/6/27 must be 55 nights or more. • Animals/Pets, No Pets: This is a no pets property. A $150/day fee will apply for violations, and you may be asked to vacate the premises with no refund (at the discretion of Portoro). Portoro follows ADA guidelines, and any additional community or HOA rules may apply. • No Smoking: This is a no smoking property. Penalty fees apply for violations, and you may be asked to vacate the premises with no refund at the discretion of Portoro. • No Parties or Events: Parties and events are not permitted. • Quiet Hours: 10:00pm-8:00am. These hours reflect local residential expectations, please keep noise low and be mindful of neighbors. • The Quechee Club, NOT Included: This home is not located in Quechee, Vermont; The Quechee Club access is not included with this rental. • Report Damages: Any known damages incurred during your stay must be reported to the property manager immediately. • Security: Some Portoro properties have exterior-only cameras for monitoring. • Seasonal Outdoor Amenities: Grills, patios, decks, and other outdoor amenities, including outdoor furniture, are seasonally available and may be unavailable or limited due to weather or local conditions. Availability is not guaranteed outside the primary season, and some items may be removed, covered, or stored at certain times of year for safety. • Local or Property Water Features: Some Portoro properties may have hot tubs, ponds/streams, or other nearby water features. There is no guard around water features, use at your own risk. • No Feeding Wildlife: Feeding wildlife is strictly prohibited at all properties to avoid property damage and to protect animals. Additional cleaning, sanitation, and remediation fees may apply (at the discretion of Field & Farm Vacation Homes by Portoro/Portoro Homes Inc. and/or any applicable HOA/association). • Wildlife + Pests: You may see local wildlife during your stay (deer, bears, coyotes, raccoons, skunks, rodents, etc.). Please keep the home and outdoor areas free of food and trash, secure all garbage in the provided bins and never leave food outside. For homes that include/offer BBQs, please bring all food items inside and scrape grills clean after use to avoid attracting wildlife. The home is regularly treated for pests, but it’s not unusual for an occasional insect to make an appearance. Please note that this is a working farm. The driveway is shared with the Farm Manager, who happily will show you around! Their living quarters are in a separate barn on the property, across from where you’ll stay.

RoundTop Chalet – Hot Tub, Fire Pit & Mountain Views Relax in your own private mountain hot tub at RoundTop Chalet, a three-bedroom, two-bath vacation home in Plymouth, Vermont. Perfectly located between Killington and Okemo resorts, this modern-rustic retreat features vaulted pine ceilings, wide windows, and a spacious open floor plan ideal for families and small groups. Mini-split heating and cooling systems in every room provide personalized comfort throughout the home. The great room offers a gas fireplace and panoramic Green Mountain views. The kitchen is fully equipped with stainless-steel appliances, stone countertops, and everything needed for easy meals at home. Upstairs, the primary suite includes a king bed and private bath. The lower level adds two more bedrooms, a full bath, laundry, and a second lounge area for movie nights or kids’ space. Step outside to a wraparound deck with grill and outdoor dining area, or unwind in the private hot tub. Evenings by the fire pit are peaceful and star-filled, surrounded by quiet woods. RoundTop Chalet sits just nine minutes from the Killington Skyeship Gondola, seventeen minutes from Okemo Mountain Resort, and twenty-three minutes from Pico Mountain. Lakes, hiking trails, and snowmobile routes are all close by. Guests who book this home through Simple Vacation Rentals can access limited discounts on Killington lift tickets and ski-rental gear, available while supplies last. Whether it’s ski season, summer on the lakes, or fall foliage adventures, RoundTop Chalet offers the perfect Vermont escape - comfortable, scenic, and close to everything. Notes: • Round Top Rd. can get slippery in the winter. The road and driveway are frequently plowed, but drivers coming up during the winter should have AWD, 4X4, or chains as needed. • Want to save on your ski trip? Book with us and get great discounts on ski and snowboard rentals - more skiing, more savings! • The hot tub is included for the peak ski season (late-December to mid-March). For other periods, there is an optional $195 set up fee. You understand use of hot tub is at your own risk and that special risks may be involved in using the hot tub. You accept full responsibility for any bodily injury arising from use of the hot tub, and hold owner and property manager harmless. • Our minimum rental age is 25. • We will provide you with door codes for our smart locks to come and go as you please and for contactless check in and out. • We have some flexibility around our standard check in and check out times depending on other bookings. Guaranteed early check in or late check out may be available for an additional charge. • Our entire home is non-smoking (e-cigs included). You may only smoke outside. There is a $500 fine for smoking in the house. • You must e-sign and return our written rental agreement after you complete your booking. • For your safety and ours, we have a camera on the house pointed at the driveway which records all the time. Cameras are not in any of the living areas. • Quiet hours are from 10pm - 8am. We use Minut, smart home technology that measures volume levels throughout the property and allows us to respond to noise nuisances without disrupting your stay. Minut is 100% privacy compliant and is required on this property. If you have any questions, please ask. We are committed to your comfort so please let us know if we can do anything during your stay to make it more enjoyable. • Fireworks are not permitted. • Winter weather is unpredictable. We do not offer weather-related refunds and recommend purchasing travel insurance for any unforeseen events.

Welcome to Trailside Village Condo #1 – Your Ultimate Slopeside Escape! This beautifully appointed 1-bedroom, 1-bathroom condo provides true ski-in/ski-out access on Killington’s Great Eastern Trail (weather permitting). Designed for up to 4 guests, it features a king bed in the bedroom and two sofa beds in the cozy living area. The open-concept living space offers a wood-burning stove (firewood included), smart TV, and high-speed Wi-Fi for entertainment. The fully equipped kitchen includes modern appliances, cookware, and dining essentials. Step onto the private deck with a BBQ grill and unwind in the outdoor hot tub under the stars (hot tub fee applies mid-March to mid-December). After a long day, rejuvenate in the cedar sauna or enjoy the spacious bathroom with a tub and shower. Additional amenities include an in-unit washer/dryer, private parking, and pet-friendly accommodations (pet fee applies). Perfectly located, this slopeside retreat is minutes from Killington’s shops, dining, nightlife, and outdoor activities like skiing, hiking, and biking. Book Trailside Village Condo #1 now for a relaxing and unforgettable Vermont getaway! • Ski On/Off: This home is located on the Great Eastern ski trail and offers ski on/off access when the trail is open. Early/late season trail conditions are weather-dependent, and neither the host nor property manager is responsible for these conditions. Reservations cannot be canceled due to weather or lack of snow. For up-to-date trail information, visit the Killington Resort website before booking. Your dates may fall under early/late season rates. • Rental Agreement: Guests must e-sign and return our written rental agreement. • Hot Tub: The hot tub is included for peak ski season weekends (late December to mid-March). For all other periods, there is an optional $195 setup fee. You understand that use of the hot tub is at your own risk and that special risks may be involved in using the hot tub. You accept full responsibility for any bodily injury arising from use of the hot tub, and hold owner and property manager harmless. • Guest Occupancy: Do not exceed the agreed guest occupancy. Over-occupancy will result in immediate eviction and fines. • Minimum Rental Age: Guests must be 25 years or older to rent this property. • Shoes: Please do not wear shoes inside the house. • Check-In/Out: Smart lock door codes will be provided for contactless check-in and check-out. While we offer some flexibility with check-in and check-out times depending on other bookings, guaranteed early check-in or late check-out may be available for an additional fee. • Smoking Policy: The entire home is non-smoking, including e-cigarettes. Smoking is only permitted outdoors. A $750 fine will be charged for smoking inside the house. • Cameras: For safety and security, there are exterior cameras on the property capable of recording at all times. There are no cameras in any living areas. • Quiet Hours: Quiet hours are from 10 PM to 8 AM. The property may use Minut, a smart home device that monitors noise levels to address disturbances without disrupting your stay. Minut is 100% privacy compliant and required for this property. Please reach out if you have questions. • Fireworks: Fireworks are not permitted at this property. • Parties/Events: Parties and events are not allowed. • Pets: This property is pet friendly with the payment of our non-refundable pet fee per dog. • Winter Weather: Winter weather can be unpredictable. We do not offer refunds due to weather or ski trail conditions and recommend purchasing travel insurance for unforeseen events. All-wheel drive and winter tires are strongly recommended. • Limitation of Liability: The owner and their rental agent shall not be held liable for any injuries or damages to the tenant, the tenant’s family, or guests that occur during the tenant’s occupancy of the property. The Tenant agrees to indemnify and hold the property manager and their representatives harmless from any and all claims, liabilities, or legal actions arising from the Tenant’s use or occupancy of the premises. SKI ON / SKI OFF: Great Eastern Trail, just out the door! Typically open January to March, so please confirm weather conditions. SKI RESORTS: Bear Mountain Lodge (1.4 miles), Skyeship Base (1.7 miles), Killington Snowshed Base (3.5 miles), Killington K1 Base (4.3 miles), Pico Mountain (9.1 miles) GOLF: Killington Golf Course (3.2 miles), Green Mountain National Golf Course (9.6 miles) NIGHTLIFE / DINING: Pickle Barrel (5.2 miles), Wobbly Barn (4.7 miles), Preston’s (3.2 miles), Choices (3.7 miles) WEDDINGS: Killington Grand Resort Hotel (3.2 miles), Mountain Top Inn & Resort (20.1 miles) AIRPORT: Rutland Regional Airport (24.1 miles), Burlington International Airport (80.3 miles), Albany International Airport (108 miles), Manchester-Boston Regional Airport (110 miles), Boston Logan Airport (153 miles)

Welcome to Gondola Lodge! This private, four-bedroom home is a short driving distance from the Skyeship gondola and only three miles from Bear Mountain Lodge. Take a walk or snowshoe on the dead-end street and enjoy the view of the river. This location provides you and your beloved group with great skiing, snowmobiling, hiking, biking, and golfing opportunities. New to the vacation home market, this home is newly constructed with all the modern furnishings needed for a breezy stay! Nestle in and relax in front of any of the four stone fireplaces. The spacious kitchen is the perfect entertainment space with a beautiful coffee bar. The open-concept living/dining area spills onto the wrap-around deck with an outside fireplace. The second level features three bedrooms and a second family/game room. The third level is a primary suite with a private bath and another stone fireplace. With two levels of bedrooms, a full bath on every level, and two family rooms, this home is great for two small families or multi-generations looking for plenty of room to spread out. Additionally, this retreat has a newly added washer/dryer for your laundry needs. THINGS TO KNOW This vacation rental is not equipped with air-conditioning. Streaming services available with guests’ own account(s). Town of Killington Short Term Registration Number: 007622 Vermont Meals and Room Tax Number: MRT-11472019

For your next family reunion or company outing, consider the Sunburst Chalet as the place to stay, play, and enjoy Killington Vermont! As one of the largest premiere rental house properties in Killington, this house is able to accommodate a maximum capacity of 25 guests. With both indoor and outdoor hot tubs, everyone can relax and unwind after a hard day on the slopes. Multiple flat screen TVs and two fireplaces allows you to spread out and enjoy every ones company. There are two spacious kitchens and several gas grills on the deck to feed your large crowd. The Green Mountains offer many summer activities for the outdoor enthusiast. Killington Resort offers mountain biking trails for all abilities, zip lines and a free fall jump tower for the dare devils and more in the Adventure center. Hike Vermont’s Long Trail or branch off on to the Appalachian Trail and discover amazing views and water falls. Rent a Kayak and spend a bucolic day on Kent Pond or go river tubing on the White River. History buffs can enjoy visiting many Revolutionary battlefields as well as taking a trip to The Calvin Coolidge Homestead and Library in Plymouth, VT just 15 minutes from Killington. Woodstock, the quintessential Vermont town, is home to the Billings Farm and Museum and the Marsh-Billings-Rockefeller National Historical Park. Vermont’s best public golf course, Green Mountain National Golf Course, is located right here Killington as well as the very challenging Killington Golf Course. We have everything for the whole family. This spacious retreat has seven bedrooms and five baths. The sleeping configurations are almost endless. The main level has three bedrooms with queen beds, and two bathrooms. The lower level has two queen bedrooms, a bedroom with three bunk beds, a bedroom with a queen bedroom and a bunk bed, and a queen sleeper sofa for that extra space. Sunburst Chalet is one of the best big house vacation rentals that Killington has to offer!

Look no further for the ultimate ski retreat, where you can watch the gondolas go by from the living area and spacious deck of this four-bedroom Killington home. Mountain views and a short walk to great slopes mean you can’t go wrong with this lovely vacation rental. Snow-capped trees surround the lodge-style home, which is located less than a quarter-mile from Killington’s beginner-level Great Eastern Trail and intermediate-level Home Stretch Trail. This home was recently renovated. In the living room, lofted ceilings emphasize the large windows facing the woods and majestic ski gondolas floating by outside. Warm up by the rustic stone fireplace, use the WiFi to check the snow report, or watch a DVD on the 50-inch cable TV. In the updated full kitchen nearby, maple cabinetry, granite countertops, and all the essential appliances ensure you have everything you need. Whether you’re dining at the table inside or lounging on the deck for an al fresco meal, there are plenty of spots to take in the rustic, woodsy vibe at this locale. Thanks to four bedrooms and two full bathrooms, will sleep up to eight people. The first bedroom is located off the kitchen and features a king bed and a full bathroom. Downstairs, there’s a bedroom with a queen bed and a private TV and DVD player, another full bath, and two more rooms with twin-over-full bunk beds in each. Killington, VT is a scenic New England destination for nature-lovers and anyone looking for hikes, mountain biking, and of course, winter recreation. Visit in the fall for stunning foliage, in the winter for plenty of skiing, or in the summer to make the most of the variety of trails and hiking opportunities. Book the mountain retreat of your dreams at this spacious lodge getaway in the Killington Peak area! Town of Killington Short Term Registration Number: 007900 Vermont Meals and Room Tax Number: MRT-11472019 THINGS TO KNOW

The Shredquarters is your ultimate basecamp for four-season mountain adventures. Just minutes from Killington Resort’s world-class skiing and mountain biking, you’ll also find hiking trails, golf courses, and endless outdoor activities right on your doorstep. The chalet spans two floors with plenty of room for 8 guests. The upper level features a well-equipped kitchen that flows into a large dining and living area, with a wood-burning fireplace (firewood provided) and 55” Smart TV. The primary bedroom on this level includes a queen bed and full bath. Downstairs you’ll find two additional bedrooms – one with a queen bed and another with two sets of bunk beds – perfect for families or groups. Plus, a full bathroom, updated ski room with space for all your gear, and dedicated office for those mixing work and play. Outside, the wrap-around, covered deck offers stunning views of Killington and Pico peaks, perfect for morning coffee or après-ski. \- Be sure to list the correct number of guests so we can keep things running smoothly (we might have a small per-person charge to cover expenses). \- We love a good time, but our minimum age for renting is 25. \- Come and go as you please with our easy-peasy smart lock access codes! \- We get it—flexibility is key! We can offer early check-in or late check-out for a small extra fee if our schedule allows. \- Our home is a smoke-free zone (e-cigs included!). A $500 fine will apply if you light up indoors. \- For everyone’s safety, we’ve got an exterior camera keeping an eye on the driveway. \- Quiet time is from 10 PM to 8 AM—let’s keep the noise down so everyone can rest easy! \- Your furry friends are welcome—up to two dogs for a $155 pet fee. (No cats allowed, though—they might just cause a ruckus!) \- No washer/dryer on-site—be sure to pack accordingly! \- Winter weather can be unpredictable, so we don’t offer weather-related refunds. We recommend travel insurance and, for your safety, all-wheel drive and winter tires are a must!

Welcome to your perfect mountain getaway at Mt. Green Resort in Killington, VT. Nestled just steps away from the renowned Killington Ski Resort, this cozy 1-bedroom condo offers the ultimate convenience for ski and snowboard enthusiasts. The interior is thoughtfully designed with a fully equipped kitchen with Nespresso machine for the coffee-enthusiasts, allowing you to prepare your favorite meals with ease. The dining table offers seating for four. The spacious living room features comfortable seating, an electric fireplace, and a smart TV, perfect for relaxing after a day on the slopes. Step out onto the private balcony to take in the breathtaking mountain views and crisp, fresh air. The bedroom is furnished with a plush queen-sized bed, ensuring a restful night’s sleep. There is also a smart TV and electric fireplace. Additional sleeping arrangements are available with a sofa bed and memory foam rollaway bed in the living room, making this condo suitable for up to four guests. The bathroom is modern and clean, stocked with essentials for your stay. As a guest at Mt. Green Resort, you’ll have access to an array of amenities designed to enhance your vacation experience. Enjoy a swim in the indoor pool, unwind in the hot tubs, or maintain your fitness routine in the well-equipped gym. For ultimate relaxation, visit the on-site spa for a soothing massage or treatment. The resort also features a convenient on-site restaurant, serving delicious meals, and a ski shop where you can rent or purchase gear. (See seasonal schedule below.) Transportation to the mountain is a breeze with the complimentary shuttle service from Thanksgiving to Easter, ensuring you can hit the slopes without any hassle. The condo’s prime location also means you’re close to local dining, shopping, and entertainment options in Killington. We also offer discounted ski and snowboard rentals to our guests. Ideal for skiers, snowboarders, and nature lovers, this charming retreat promises a memorable and relaxing stay. Whether you’re here for an adventurous winter getaway or to explore the beautiful landscapes during the warmer months, Mt. Green Resort offers the perfect home base.​​​​​​​ CONSTRUCTION NOTICE: Our building is not part of the Mountain Green summer 2026 construction project. However, Buildings 1 and 2 nearby are getting new siding, windows, and doors from May through December 2026, so some daytime construction noise is possible. • Want to save on your ski trip? Book with us and get great discounts on ski and snowboard rentals - more skiing, more savings! • RESERVED INDOOR PARKING SPOT: You have spot #6 reserved for one car. • Indoor amenities (Building 3): Pool, hot tubs, saunas, and steam room open daily from 9 AM to 9 PM; fitness center open 24/7. Key cards (in condo) required for access. • Outdoor amenities (between Buildings 1 & 2): Seasonal heated saltwater pool, BBQ grills, and fire pit (Memorial Day to mid-September, 9 AM–10 PM). Key cards required. • The free shuttle service to the resort leaves every 15 minutes outside the condo from Thanksgiving to Easter. We are also only a 7 minute walk to Snowshed Lodge. • There are Tesla destination chargers available in the upper Snowshed parking lot - a short walk from the condo. Non-Tesla EVs may use these with an J1772 adapter. Overnight parking is not allowed there. • We have some flexibility around our standard check in and check out times depending on other bookings. Guaranteed early check in or late check out may be available for an additional charge. • We will provide you with door codes for our smart locks for contactless check in and check out. No one will meet you at the property. •• Our entire property is non-smoking and non-vaping, including balconies and decks. You may only smoke outside and 75 feet away from the building. Please properly dispose of all butts. • Quiet hours are from 10pm - 8am. • We welcome families and occupants over the age of 25. We have a strict rule of no parties, large groups or events at this property. • Pets are not allowed. There will be a $450 fine for any unauthorized pets. • You must sign and return our written rental agreement. • A community laundry room is available in each building. The condo does not have its own washer and dryer. • Winter: Building maintenance may access the condo to shovel decks and patios to prevent ice buildups and leaks. This is a homeowner’s association requirement and we appreciate your cooperation. • The entire town has well water that is high in mineral content. We recommend bringing bottled water if you do not like the "taste" of well water. • Winter weather is unpredictable. We do not offer weather-related refunds and recommend purchasing travel insurance for any unforeseen events. All wheel drive and winter tires are also recommended. SKI RESORTS: Killington Snowshed Base (0.4 miles), Killington K1 Base (1.1 miles), Pico Mountain (6.2 miles), Mountain Meadows Cross Country Ski and Snowshoe (3.9 miles) SHUTTLE: Every 15 minutes outside the condo from Thanksgiving to mid-March. GOLF: Killington Golf Course (0.3 miles), Green Mountain National Golf Course (6.3 miles) NIGHTLIFE: Pickle Barrel (2.1 miles), Wobbly Barn (1.6 miles), Nitespot (1.0 mile), The Foundry at Summit Pond (2.7 miles) WEDDINGS: Killington Grand Resort (0.3 miles), Mountain Top Inn & Resort (17.1 miles) AIRPORT: Rutland Regional Airport (20.7 miles), Burlington International Airport (77.2 miles), Albany International Airport (113 miles), Manchester-Boston Regional Airport (116 miles)

Elegant one-bedroom unit located .06 miles from the Killington resort, newly renovated with fresh decor. This one-bedroom unit has a single King-sized bed in the master bedroom and a pull-out sofa in the living room. The bathroom is equipped with a step-in tub/shower. Perfect for a family weekend getaway at the Killington ski resort. The kitchen has a cozy feel and is outfitted with a dishwasher, a full-size refrigerator, a full-size electric oven/stove, a drip coffee maker, and a microwave. The unit features a living room area combined with a dining area and seating for four people. The living room gives access to a small balcony to enjoy the Killington mountain fresh air. For entertainment, each room has a flat-panel tv and Wi-Fi internet connection. Complementary parking is available onsite. Washer and dryer included in the unit. The outdoor pool, hot tub, and, tennis courts are open during summer only. (please note this unit has no air conditioning) Beautiful golf course right next door! NEW FOR THE 2026 SEASON! The Pinnacle Hot Tub and Lounge in Killington, Vermont, offers a relaxed and comfortable après-ski environment for guests. The facility features a 20-person hot tub, a steam room, and a sauna, coming soon. Guests can enjoy a beer and wine bar with light snacks on site, and complimentary towels are provided. The lounge is open Daily from 3:00 p.m. to 9:00 p.m.,( subject to staffing availability) making it the perfect place to relax after a day on the slopes. • Killington Resort extensive system of mountain biking trails. • Killington Adventure Center – Zip Lines, Mountain Coaster, Free Fall Jump Tower and more • Hiking – Vermont’s Long Trail, Appalachian Trail • Kayaking – Kent Pond, Woodward Reservoir and Chittenden Pond and more • Coolidge Homestead – Vermont’s #1 visited site in Plymouth VT only 20 minutes away • Woodstock VT filled with wonderful shops and art galleries • Marsh Billings Rockefeller National Historical Park in Woodstock VT • Billings Farm Museum – a wonder family activity • Green Mountain Golf Course – the # 1 public course in the state • Killington Golf Course owned by the resort • VINS – Vermont Institute of Natural Science – a rescue and birth sanctuary.

Nestled alongside the picturesque Black River, this charming 4-bedroom, 2-full bathroom house in Plymouth, VT, is the perfect retreat for families and dog lovers alike. With its stunning riverfront location, you can enjoy breathtaking views and a plethora of outdoor activities such as kayaking, fishing, and bird watching right at your doorstep. This home is ideally situated between the renowned ski destinations of Killington and Okemo, making it a fantastic base for winter sports enthusiasts. Inside, you’ll find a cozy living space complete with a wood-burning fireplace, perfect for warming up after a day on the slopes. The fully equipped kitchen features modern appliances, including a Nespresso coffee maker, ensuring you can start your day with a fresh brew. The property also offers an office space and essential amenities like a washer/dryer, internet access, and an electric vehicle charger (non Tesla/J1772 Level 2 charger), making your stay comfortable and convenient. Whether you’re looking to explore the scenic beauty of the area or simply relax by the river, this dog-friendly home provides a secluded escape with easy access to local attractions. Enjoy the vibrant downtown of Okemo for shopping and dining, or take advantage of the nearby hiking and biking trails. With its combination of comfort, convenience, and natural beauty, this Plymouth getaway is the ideal destination for your next vacation. Book your stay today! Vermont Meals and Room Tax Number: MRT-11472019

Beautifully renovated one-bedroom condo just 0.06 miles from Killington Resort, thoughtfully decorated to capture Vermont’s cozy mountain charm. Ideal for a family weekend getaway or a couples’ escape, this unit comfortably sleeps up to four guests. Beautiful golf course right next door! The bedroom features a queen-sized bed, while the living room includes a pull-out sofa. The bathroom offers a convenient step-in tub/shower. The fully equipped kitchen has everything you need for home-cooked meals, including a full-size electric stove/oven, full-size refrigerator, dishwasher, microwave, and drip coffee maker. The open-concept living and dining area includes seating for four and opens onto a private balcony—perfect for enjoying the fresh Killington mountain air. For entertainment and convenience, each room is equipped with a flat-panel TV and complimentary Wi-Fi. Free on-site parking is included. GRAND REOPENING FOR THE 2026 SEASON! The Pinnacle Hot Tub and Lounge offers a relaxed and welcoming après-ski experience right in Killington. Guests can unwind in a spacious 20-person hot tub and enjoy access to a steam room and sauna (coming soon). The lounge features a beer and wine bar with light snacks, complimentary towels, and Wi-Fi for guest use. The lounge is open Daily from 3:00 p.m. to 9:00 p.m.,( subject to staffing availability) making it the perfect place to relax after a day on the slopes. Killington Resort—“The Beast of the East”—offers the most skiable terrain in the region, top-tier snowmaking, and legendary après-ski nightlife. The mountain caters to all skill levels, with lessons ranging from beginner to advanced instruction led by seasoned professionals, including former Olympians. Beyond skiing and riding, the Killington area offers year-round fun for everyone: snowmobiling tours through the Green Mountains, tubing, ice skating at Foundry Pond, and vibrant nightlife at local favorites like the Wobbly Barn, Pickle Barrel, and Jax’s. Come experience Killington—where unforgettable mountain memories are made. • Killington Resort extensive system of mountain biking trails. • Killington Adventure Center – Zip Lines, Mountain Coaster, Free Fall Jump Tower and more • Hiking – Vermont’s Long Trail, Appalachian Trail • Kayaking – Kent Pond, Woodward Reservoir and Chittenden Pond and more • Coolidge Homestead – Vermont’s #1 visited site in Plymouth VT only 20 minutes away • Woodstock VT filled with wonderful shops and art galleries • Marsh Billings Rockefeller National Historical Park in Woodstock VT • Billings Farm Museum – a wonder family activity • Green Mountain Golf Course – the # 1 public course in the state • Killington Golf Course owned by the resort • VINS – Vermont Institute of Natural Science – a rescue and birth sanctuary.

Dancing Bears is a two home compound in the heart of Killington. Great location just off the access road, minutes to the slopes, walking distance to the market, restaurants and shuttle. Enjoy 2 homes on 2.7 gorgeous acres. Plenty of space for friends and family to connect and relax. Two hot tubs, 2 game rooms, 4 TVs, tons of indoor and outdoor space to make wonderful memories with friends and family. Enjoy 8 bedrooms with new luxurious linens, 4 baths and fully stocked kitchens. There are two homes on the property, each sleeps 10 and has 4 bedrooms and 2 baths. There is ample parking onsite and the homes are accessed via smart lock, so you will receive a code for the doors.

Discover one of Vermont's hidden gems when you book this Plymouth vacation rental, known as the 'Mountain Casa'. Featuring 4 floors of impeccably curated living space, a grandiose private indoor pool, a fully equipped kitchen, and a location central to Okemo Mountain and Killington ski slopes, this 4-bedroom, 5.5-bath home provides the perfect backdrop for an unforgettable family getaway. Ski the day away, then come 'home' for a relaxing dip in the pool complete with its own stone waterfall! -- THE PROPERTY -- MRT-11153470-001 | Sauna | Laptop Friendly | 5,000 Sq Ft | Maximum Occupancy of 8 Per HOA Rules Seamlessly blend outdoor excitement with luxury R&R for a unique Green Mountain State experience that will keep you, your friends, and your family coming back for more! Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin Beds OUTDOOR LIVING: 3 furnished outdoor areas, dining set INDOOR LIVING: 2 Smart TVs, books, Alexas on each floor, 2 fireplaces, en-suite bathroom(s), bathrobes, dining table, wet bar, private indoor pool KITCHEN/KITCHENETTE: Fully equipped, drip coffee makers, coffee grinder, microwave, toaster, blender, KitchenAid stand mixer, ice maker, dual ovens, cooking utensils, cutlery, spices, dishware & flatware, breakfast bar GENERAL: Free WiFi, central heating & A/C, security system, complimentary toiletries, pool towels, towels/linens, washer/dryer, pool toys FAQ: Stairs required for access (indoor & outdoor), 4WD recommended in winter, external security cameras (3 cameras, facing out), no pets allowed PARKING: Driveway (3 vehicles), street parking (first-come, first-served) -- THE LOCATION -- SKI THE SLOPES: Okemo Mountain Resort (10.0 miles), Killington Ski Area (15.7 miles), Pico Mountain Ski Resort (18.5 miles), Suicide Six (23.0 miles), Magic Mountain (28.0 miles), Bromley Mountain Ski Resort (32.4 miles), Mount Sunapee Resort (44.8 miles) HIKE & BIKE: Camp Plymouth State Park (3.7 miles), Coolidge State Park (8.1 miles), Healdville Trail (11.5 miles), Thundering Brook Falls (16.0 miles), Deer Leap Trail (18.8 miles) HISTORIC SITES: Calvin Coolidge State Historic Site (5.8 miles), Marsh-Billings-Rockefeller National Historical Park (20.2 miles), Saint-Gaudens National Historical Park (28.0 miles) ENTERTAINMENT: Long Trail Brewing Company (11.3 miles), Vermont Country Store (19.8 miles), Harpoon Brewery (28.4 miles), Silo Distillery (28.4 miles) NEARBY TOWNS: Ludlow (10.0 miles), Killington (15.7 miles), Woodstock (19.7 miles), White River Junction (33.8 miles) AIRPORT: Rutland Southern Vermont Regional Airport (24.7 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - Absolutely no pets allowed. Violation of this rule may result in eviction from the property - No smoking - No events, parties, or large gatherings over the maximum occupancy. Violation of this rule may result in eviction from the property - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs and may be difficult for guests with limited mobility - NOTE: 4-wheel drive or all-wheel drive is necessary in the winter months to access the property - NOTE: Your safety matters. There are 3 security cameras, located at the front door, driveway, and lower-level patio door, facing out. They do not look into any interior spaces

Welcome to our mid-century modern chalet, perfect for a serene wooded mountain escape year-round. Recently renovated, this home offers all the comforts to make you feel right at home. Enjoy a cozy getaway with family and friends in this beautifully designed retreat. The Space Our newly designed and furnished chalet is equipped with everything you need for a comfortable stay. Conveniently located, this fully renovated home accommodates up to eight guests in four bedrooms and two bathrooms. Enjoy modern amenities, including new appliances, fast and reliable WiFi, and two 55” HD televisions. The gas fireplace warms the living room, providing a cozy atmosphere with enough seating for everyone to enjoy movie nights. Outdoor Spaces Upper Deck: Start your day with morning coffee alfresco, seated at the tables and chairs. A grill is also available for outdoor cooking. Lower Deck: Perfect for warmer months, this beautifully lit seating area is ideal for gatherings with friends. Open a bottle of wine and unwind. Newly Added Hot Tub: Relax in the newly added four-person hot tub, perfect for soothing sore muscles after a day of adventure. • The hot tub is included for the peak ski season weekends (late-December to mid-March). For other periods, there is an optional $195 set up fee. You understand use of hot tub and sauna is at your own risk and that special risks may be involved in using the hot tub. You accept full responsibility for any bodily injury arising from use of the hot tub, and hold owner and property manager harmless. • Please be sure that you have entered the correct number of guests. • Our minimum rental age is 25. • We will provide you with access codes for our smart locks to come and go as you please. • We have some flexibility around our standard check in and check out times depending on other bookings. Guaranteed early check in or late check out may be available for an additional charge. • Our entire home is non-smoking. There is a $500 fine for smoking in the house. • Quiet hours are from 10pm - 8am • Fireworks are not permitted. • Winter weather is unpredictable. We do not offer weather-related refunds and recommend purchasing travel insurance for any unforeseen events. All wheel drive and winter tires are also recommended. SKI RESORTS: Killington Snowshed Base (3.0 miles), Killington K1 Base (3.7 miles), Pico Mountain (3.3 miles), Mountain Meadows Cross Country Skiing (1.0 mile) GOLF: Killington Golf Course (3.0 miles), Green Mountain National Golf Course (3.5 miles) NIGHTLIFE: Pickle Barrel (0.9 miles), Wobbly Barn (1.4 miles), Nitespot (2.0 miles), The Foundry at Summit Pond (0.3 miles) WEDDINGS: Killington Grand Resort (3.1 miles), Mountain Top Inn & Resort (14.2 miles) AIRPORT: Rutland Regional Airport (18.6 miles), Burlington International Airport (74.4 miles), Albany International Airport (113 miles), Manchester- Boston Regional Airport (116 miles)

Discover luxury slope-side living at this Killington Resort condo. Primed for wintertime recreation, this elegant escape boasts unbeatable access to world-class slopes, just a short walk or shuttle ride away. Plus you’ll have access to an indoor pool, hot tub, and sauna to help you rest and recharge after the day’s runs. An ideal getaway for any time of year, Killington Mountain Resort offers a bounty of activities and attractions to enjoy outside of ski season. There is also gym equipment available, as well as a game room which offers a billiards table and arcade games. The condo’s second-floor location is ideal, with no noise above you and unobstructed views of the grounds. The Trail Creek Ski Home Trail leads directly from the mountain slopes to the base of the stairs for the condo, while the Trail Creek Amenities Building is directly across the way. This area also has much to offer outside the resort, with endless food and drink options, specialty shops, live music, and seasonal events to discover just a short drive from home. Cozy up on the luxurious leather sofa while streaming your favorite shows and movies on the smart TV or just relax and enjoy the warmth of the wood-burning fireplace set in gorgeous indigo granite mined straight from the Chippewa Stone Quarry. An up-cycled hickory barn beam mantle dating from the 1840s further adds to the piece’s beauty. Cured firewood is available at four different woodsheds situated around the Trail Creek grounds for your convenience. The stainless steel full kitchen has everything you need for home cooking, including a dishwasher for easy cleanup. From coffee to après-ski beverages, the private balcony offers a scenic perch to enjoy views of Trail Creek and the surrounding forest. Town of Killington Short Term Registration Number: 006174 Vermont Meals and Room Tax Number: MRT-11472019​​​​​​​ RESORT AMENITIES - Pool - Hot tub - Sauna - Gym - Game room - On-site ski lift access

Delight in this friendly, fully renovated (2022) modern ski condo next to Killington’s popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65" TV. Enjoy the Whiffletree condo association’s outdoor pool and tennis courts in the summer. Our condo was just renovated in 2022 to give it a fresh, fun feel while elevating your Vermont experience. It is perfectly geared for a couple, family or a few friends to use as a home base for skiing, boarding, leaf-peeping, hiking, golfing, mountain biking, or just experiencing Vermont. Parking is included and is in the lot right in front of the building. There are stairs to access the apartment. We have keypad lock on the door so you can come and go as you please, but we are available to help if needed. We’ll send you a complete guide to CozyCub with key codes, wifi info, directions, guest information, and can offer suggestions for things to do and places to go during your stay, if you’d like. CozyCub is well situated right next to the most popular base areas of the Killington resort. The Killington Golf Course is right next door and an easy walk -- In the winter, it hosts the tubing area. Whiffletree also has a pool, tennis courts, BBQ picnic area, jungle gym, and Gazebo with views over the golf course and far into the Green Mountains. Killington is known for offering the most extensive ski trails in the Northeast, and is an amazing base for mountain biking, leaf peeping, apple picking, enjoying great restaurants with friends, snow mobiles, and much more! If you are just looking to relax, book a massage across the street, take a walk down Killington Road, or cuddle up for a binge streaming night. As a part of the Whiffletree condos at Killington, CozyCub has a Ski-Off trail, so anyone in your party can end their day on the slopes when they choose. To get to the base areas, you can wait for the regular shuttle at the end of the parking lot, or walk 1/2 mile to Killington’s full-service Snowshead base area.

Whiffletree F6 is a beautifully renovated 2-bedroom, 1-bathroom condo located at the base of Killington Resort, offering the best of both winter and summer. Whether you’re here for skiing, snowboarding, hiking, or mountain biking, this stylish and comfortable retreat is perfect for families, couples, or small groups. In the summer, you can enjoy Whiffletree’s outdoor heated pool, tennis courts, and a playground for the kids, while exploring nearby hiking trails and the Killington Adventure Center. In winter, the condo offers easy access to the slopes via shuttle, and conditions permitting, you can ski right back to your unit. Inside, the condo features a cozy living space with a queen bed in Bedroom 1 and a full bed in Bedroom 2. The updated kitchen and living area provide all the comforts you need after a day of adventure. Please note: the gas fireplace is currently inoperable and will not be repaired until after the season. Whiffletree F6 is the perfect base for all-season fun in the heart of Killington. • Killington Resort extensive system of mountain biking trails. • Killington Adventure Center – Zip Lines, Mountain Coaster, Free Fall Jump Tower and more • Hiking – Vermont’s Long Trail, Appalachian Trail • Kayaking – Kent Pond, Woodward Reservoir and Chittenden Pond and more • Coolidge Homestead – Vermont’s #1 visited site in Plymouth VT only 20 minutes away • Woodstock VT filled with wonderful shops and art galleries • Marsh Billings Rockefeller National Historical Park in Woodstock VT • Billings Farm Museum – a wonder family activity • Green Mountain Golf Course – the # 1 public course in the state • Killington Golf Course owned by the resort • VINS – Vermont Institute of Natural Science – a rescue and birth sanctuary.

Welcome to Trail Creek Unit #74—our inviting two-bedroom + loft condo. Just a short walk to Snowshed Lodge, next to the Killington Grand Resort, and across the street from the Killington Golf Course, this top-floor retreat offers peace, privacy, and ski-home access in the winter. The spacious layout includes a main floor with mudroom entry, primary bedroom with king bed and ensuite bath, a second bedroom with two XL twin beds, a second full bath, living room with vaulted ceiling, a fireplace (with complimentary firewood), a full pull-out couch, a dining area with seating for six, a fully equipped kitchen, and an in-unit laundry. Proceed upstairs to the loft for two additional twin beds and an additional comfy seating area. There is fast WiFi throughout, cable TV, streaming services, and air conditioning units within the two bedrooms for summer stays. Step out onto the balcony for beautiful, wooded creek views or head to the Trail Creek Activity Center with its indoor pool, hot tubs, sauna, fitness room, and game room. Whether you’re skiing, hiking, mountain biking, golfing, or simply relaxing, this condo is the perfect home base for your Killington adventure. RESORT AMENITIES • Ski in access via green trail. • Bus shuttle service to Killington base lodges – leaves every 15 minutes outside the condo complex from Thanksgiving to mid-March on Saturdays and Sundays only. • Short 1/3 mile walk to Snowshed base lodge. • Short drive to K1 and Ramshead base lodges. • The Activity Center at the condo is open 10:00 AM – 10:00 PM and offers: Indoor saltwater swimming pool, hot tubs, sauna, exercise equipment, pool table and arcade games. • Free firewood. • Free parking for 2 vehicles. THINGS TO KNOW • Smart locks with unique code for contactless check-in. • For your safety & ours, we have a doorbell camera at the front entrance that records video only, no audio, for security purposes. It only captures the exterior entryway and does not monitor any indoor spaces. • Parking is approximately 150 feet from the condo; a short walk along a path is required. Luggage carts are available for your convenience. • Unit is located on floor 2 (no noise above). • Pack ’n play and high chair provided. • Pets are not allowed. There will be a $450 fine for any unauthorized pets. • Property is non-smoking and non-vaping. • All wheel drive and winter tires are recommended. • Quiet hours are from 10:00 PM – 8:00 AM. Town of Killington Short Term Registration Number: 007940 Vermont Meals and Room Tax Number: MRT-11472019