Large group vacation rentals in Chittenden, VT

Explore 28 large group vacation rentals, homes, and villas in Chittenden, VT for your next getaway or business trip. With space for everyone, enjoy the comfort and privacy of a home designed for gathering, alongside premium amenities such as Homes with Free Parking and Best Affordable Homes. Throughout your stay, spend time together, share meals, and relax in spacious living areas that make group travel feel cohesive. With options starting as low as $87 per night and homes offering up to 4 bedrooms and 3 bathrooms, it's easy to book a stay that fits your group. And with 24/7 local support and high-speed Wi-Fi, everyone stays connected and protected. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, making each trip more rewarding than the last. Book your next group getaway with Homes & Villas by Marriott.

28 Great for Groups in Chittenden

Inviting Chittenden Apartment Near Pico Mountain!

Pittsford, VT, US
2 Bedrooms 4 Guests
Aug 25 - 27
$334 night

Hike, boat, and ski from this wooded retreat. Nestled in nature's embrace, this serene 2-bed, 1-bath vacation rental is the perfect gem for outdoor lovers. Spend your days hiking the picturesque trails of Green Mountain National Forest, taking a scenic drive to Chittenden Reservoir, and skiing the carefree slopes of Pico Mountain. After a day of adventure, cozy up for a movie on the Smart TV or cook a delicious dinner in the well-equipped kitchen. -- THE PROPERTY -- Meals & Rooms Tax License No. MRT-11153470-001 | 2 Mini-Split A/C Units | Front Porch w/ Cushioned Seating | 2 Mi to Chittenden Reservoir | On-Site River Bedroom 1: Queen Bed | Bedroom 2: Full Bed INDOOR LIVING: Smart TV, board games, ceiling fans KITCHEN: Fridge, stove & oven, microwave, drip coffee maker, cooking basics, dishware & flatware, trash bags, paper towels GENERAL: Free WiFi (shared), baseboard heat, washer & dryer, laundry detergent, iron & board, complimentary toiletries, hair dryer, towels & linens FAQ: 1 Ring exterior security camera (facing out) ACCESSIBILITY: Single story, 2nd-floor unit, stairs to access, internal step to 2nd bedroom PARKING: Circular gravel driveway (6 vehicles) ADDT’L ACCOMMODATIONS: An additional property is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking -- THE LOCATION -- HIKE, BOAT & SKI: Chittenden Reservoir (2 miles), Mountain Top Resort (2 miles), Green Mountain National Forest (6 miles), Pine Hill Park (9 miles), Pico Mountain Ski Resort (10 miles), Killington Resort (15 miles) LOCAL STOPS: New England Maple Museum (7 miles), Wilson Castle (12 miles) FUN FOR ALL AGES: Wonderfeet Kid's Museum (9 miles), Killington Adventure Center (15 miles) AIRPORTS: Rutland Southern Vermont Regional Airport (15 miles), Manchester-Boston Regional Airport (126 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 -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story, 2nd-floor unit requires stairs to access and an additional internal step to reach the 2nd bedroom - NOTE: There's another bookable rental on-site; other travelers may be present and share WiFi connection and parking - NOTE: Your safety matters. This property features 1 Ring exterior security camera located on the front of the house, facing outward toward the driveway. It does not look into any interior spaces. The camera records video and sound when activated by motion

Duplex Unit, 2 Mi to Chittenden Reservoir!

Pittsford, VT, US
2 Bedrooms 6 Guests
Aug 25 - 27
$370 night

Whether you’re looking to ski, hike, or boat in the beauty of Vermont, this 2-bedroom, 1-bath Chittenden vacation rental has it all. You'll feel truly immersed in nature on the wooded mountains. You can experience the beauty of Green Mountain National Forest or hit the slopes at Pico Mountain nearby. Then, return to enjoy the rec room’s pool table and wood-burning fireplace or unwind by the Smart TVs of your own private space. This home’s unique set up keeps your days versatile. -- THE PROPERTY -- Meals & Rooms Tax License No. MRT-11153470-001 | Front Porch w/ Cushioned Seating | Washer & Dryer | Free WiFi (Shared) | 6 Mi From Green Mountain National Forest | On-Site River Bedroom 1: Queen Bed | Bedroom 2: Queen Bed, Full Bed PROPERTY FEATURES: Smart TV, ceiling fans, screened-in deck w/ dining area (seasonal), grill, spacious yard REC ROOM: Smart TV, pool table, wood-burning fireplace, wet bar w/ bar top seating KITCHEN: Fridge, stove & oven, dishwasher, microwave, drip coffee maker, cooking basics, dishware & flatware, trash bags, paper towels GENERAL: Iron & board, complimentary toiletries, hair dryer, towels & linens, hangers, baseboard heating, 2 window A/C units (in bedrooms), wall A/C unit (in bar room) FAQ: 1 Ring exterior security camera (facing out) ACCESSIBILITY: 2 stories, step-free entry, 1st-floor bedroom & bath PARKING: Circular gravel driveway (6 vehicles) ADDT’L ACCOMMODATIONS: An additional property is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking -- THE LOCATION -- HIKE, BOAT & SKI: Chittenden Reservoir (2 miles), Mountain Top Resort (2 miles), Green Mountain National Forest (6 miles), Pine Hill Park (9 miles), Pico Mountain Ski Resort (10 miles), Killington Resort (15 miles) LOCAL STOPS: New England Maple Museum (7 miles), Wilson Castle (12 miles) FUN FOR ALL AGES: Wonderfeet Kid's Museum (9 miles), Killington Adventure Center (15 miles) AIRPORTS: Rutland Southern Vermont Regional Airport (15 miles), Manchester-Boston Regional Airport (126 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 -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: While this 2-story home offers step-free entry and a bedroom and full bathroom on the 1st floor, interior stairs are required to access the bedroom on the 2nd floor - NOTE: There's another bookable rental on-site; other travelers may be present and share WiFi connection and parking - NOTE: Your safety matters. This property features 1 Ring exterior security camera located on the front of the house, facing outward toward the driveway. It does not look into any interior spaces. The camera records video and sound when activated by motion - NOTE: The screened-in deck is not heated and is only available in warmer months, from May to October

The Mendon Cottage

Mendon, VT, US
2 Bedrooms 6 Guests
Sep 30 - Oct 2
$203 night

Welcome to your cozy mountain retreat in Mendon, Vermont! This recently renovated 2-bedroom, 2-bathroom home offers the perfect blend of modern comfort and rustic charm, making it an ideal getaway for up to six guests. Situated conveniently close to Pico Ski Resort, Killington Ski Resort, and the town of Rutland, you’ll have easy access to all the best that this region has to offer. The master bedroom features a queen bed with an ensuite bathroom, ensuring privacy and convenience. The second bedroom is spacious, offering two double beds, perfect for families or friends traveling together. An additional bathroom and a laundry room add to the convenience of your stay. Unwind in the inviting living room, where a smart TV awaits for your entertainment needs. The fully equipped kitchen and dining area make it easy to prepare and enjoy meals together. High-speed WiFi ensures you stay connected, whether you’re planning your next adventure or catching up on work. We’re also pet friendly with a pet fee. For your comfort, the home is equipped with mini splits for both heating and air conditioning, so you can relax no matter the season. Step outside to enjoy the fresh mountain air on the front or back deck, complete with a fire pit and BBQ grill for outdoor cooking. This home has been thoughtfully updated with all new furnishings, providing a fresh, modern feel while maintaining a welcoming atmosphere. Whether you’re here for the skiing, exploring the local area, or simply relaxing, this Mendon home offers the perfect base for your Vermont escape. House Rules: - Please be sure that you have entered the correct number of guests as we may have a per-person per-night surcharge to cover expenses. You can contact us for a custom quote before booking. - Our minimum rental age is 25. - We will provide you with door codes for our smart locks 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 on the outdoor deck. 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 doorbell 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. - Up to two dogs are allowed with the payment of our $150 pet fee. - 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. - The garage and basement are not available for guest use. ​​​​​​​ SKI RESORTS: Killington Snowshed Base (8.0 miles), Killington K1 Base (8.7 miles), Pico Mountain (2.2 miles) MEDICAL: Rutland Regional Medical Center (7.3 miles) GOLF: Killington Golf Course (8.0 miles), Green Mountain National Golf Course (6.8 miles) NIGHTLIFE: McGrath’s Irish Pub (2.5 miles), Pickle Barrel (5.9 miles), Wobbly Barn (6.4 miles), Mary Lou’s (7.0 miles), The Foundry at Summit Pond (5.3 miles) WEDDINGS: The Birch Ridge (6.4 miles), Killington Grand Resort (8.0 miles), Mountain Top Inn & Resort (9.3 miles) AIRPORT: Rutland Regional Airport (13.2 miles), Burlington International Airport (92.9 miles), Albany International Airport (104 miles), Manchester-Boston Regional Airport (118 miles), Boston Logan (164 miles)

Killington A-Frame

Killington, VT, US
2 Bedrooms 6 Guests
Aug 30 - Sep 1
$314 night

The Killington A-Frame is a stylish two-bedroom, two-bathroom mountain home tucked into a quiet hillside neighborhood in Killington. Surrounded by trees and backed by the vast Green Mountain National Forest, this is your peaceful escape while still being minutes from all the action. Step inside to a bright open-concept main floor featuring a newly renovated kitchen with soapstone countertops, premium appliances including a Bertazzoni range, and a functional pantry. The cozy living area is centered around a wood stove, perfect for unwinding after a day on the slopes or trails. Both bedrooms are located upstairs, one with a queen bed and the other with two twin beds, along with a second bathroom. Designer touches like shiplap walls, curated lighting, and custom built-ins elevate the entire space. Outside, enjoy a large deck surrounded by nature, ideal for summer stargazing or year-round hot tub soaks after a day on Superstar. The hot tub is available year round with a required $195 setup fee to cover filling, balancing, and maintaining the water. Located just 12 minutes to Killington Resort, 7 minutes to Pico Mountain, and close to hiking, golf, mountain biking, and Kent Pond, this home offers the perfect balance of adventure and relaxation. • The hot tub is available year round and requires a $195 setup fee, which covers filling, balancing, and preparation prior to your stay. You understand that use of the hot tub and sauna is at your own risk and that special risks may be involved. You accept full responsibility for any bodily injury arising from use of the hot tub and agree to hold the owner and property manager harmless. • 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. • You must e-sign and return our written rental agreement after you complete your booking. • 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.

Pico Mountain Condo F106 (Pico Mountain Getaway)

Killington, VT, US
3 Bedrooms 8 Guests
Oct 31 - Nov 2
$484 night

Located right at the base of Pico Mountain, this condo gives you unbeatable ski on/off access and the relaxed, family-friendly vibe Pico is known for. You’re also just 10 minutes from Killington Resort, making it easy to enjoy the best of both mountains. (Local tip: Pico is an amazing choice on peak weekends and holidays when Killington gets busier, and it’s always a favorite for families.) This comfortable three-bedroom, two-bath condo has everything you need for a great mountain getaway. After a day on the slopes, unwind by the gas fireplace or cook dinner in the fully equipped kitchen. There’s plenty of room for everyone to spread out and relax. The layout works perfectly for families or two couples traveling with kids. You’ll find two bedrooms with queen beds and a third bedroom with two single beds. The open kitchen and living area make it easy to gather, eat, and relax after your day outside. Ski right from the condo to Pico or hop in the car for a quick drive to Killington for even more terrain and restaurants. We look forward to hosting you and think you’ll love staying here. • We have some flexibility around standard check-in and check-out depending on other bookings. Guaranteed early check-in or late check-out may be available for an additional fee. • Renters must be at least 26 years old per the condo association. • Smart lock entry allows for easy, contactless check-in. Your unique code will be sent the week of arrival. • Pack ’n play and high chair available upon request. • The entire property is non-smoking and non-vaping. Smoking is allowed only outside and 75 feet from the building. • Quiet hours are 9pm to 8am. We may use Minut smart home technology to monitor volume levels only. It is 100% privacy compliant. • For safety, a camera is located at the entryway of the condo (not inside any living areas). • No pets allowed. Unauthorized pets will result in a $450 fine. • A signed rental agreement is required. • Winter weather can be unpredictable. We do not offer weather-related refunds and recommend travel insurance. All-wheel drive and winter tires are also recommended. The Village Square at Pico Condo Association is a family-oriented community primarily used by owners and committed to the peaceful, safe and quiet enjoyment of their residences. While the Association allows rentals and encourages guests to enjoy their visit, they have implemented certain rules related to the use and enjoyment of the units. These rules allow the Association to issue fines and take other actions particularly as it relates to the enforcement of the minimum age requirement of 25, "Quiet Hours" from 9pm until 8am and their no pet policy. The Association will try to resolve issues through the owner or rental agency in the first instance but reserves the right to take action in real time as circumstances require. In short, please respect your neighbors while you are a guest in these condos. SKI RESORTS: Pico Mountain (0.1 miles), Killington Snowshed Base (6.3 miles), Killington K1 Base (7.0 miles), Mountain Meadows Cross Country (2.4 miles) SHUTTLE: Runs every 15 minutes from Thanksgiving to mid-March right outside the condo GOLF: Green Mountain National (5.4 miles), Killington Golf Course (6.3 miles) NIGHTLIFE: McGrath’s Irish Pub (0.8 miles), Flannels (2.2 miles), Pickle Barrel (4.2 miles), Wobbly Barn (4.7 miles), Nitespot (5.3 miles), The Foundry (3.7 miles) WEDDINGS: Killington Grand Resort (6.3 miles), Mountain Top Inn (11.4 miles) AIRPORTS: Rutland Regional (15.2 miles), Burlington International (71.2 miles), Albany International (108 miles), Manchester-Boston Regional (119 miles)

Pico Mountain H-304

Killington, VT, US
2 Bedrooms 6 Guests
Aug 31 - Sep 2
$188 night

Trailside Loft at Pico Village Resort H‑304 | Ski‑In/Ski‑Out in Vermont Experience the ultimate mountain getaway in this slopefront 2‑bedroom + loft, 1‑bath condo at Pico Village. Trailside Loft at Pico offers true ski‑in/ski‑out access just steps from the Golden Express lift, with a daytime shuttle to Killington’s main base for full mountain flexibility. Layout & Sleep Setup • Bedroom 1: King bed + balcony • Bedroom 2: Queen bed • Loft (open): Twin XL bed + Twin XL trundle • Total capacity: 6 guests Cozy, Renovated Interior Vaulted ceilings, wood accents, and modern upgrades set the tone for comfort. The living area features a marble wood‑burning fireplace, comfortable seating, and a 75” smart TV. The kitchen is fully renovated with granite counters and is stocked for full meals. Dining area seats 8 with additional bar seating for 3. Resort Amenities & Extras Enjoy optional access (day pass) to the Pico Sports Center’s indoor pool, hot tub, saunas, gym, yoga studio, and more. EV chargers are onsite. When you book direct with us, you’ll receive exclusive discounts on ski lift tickets and equipment rentals. Year-Round Appeal While Pico is great for skiing (57 trails, 6 lifts), it also offers summer hiking, biking, golf, waterfalls, and peaceful forest escapes. Free parking and WiFi are included. Important Note This unit sits on the third floor and is only accessible by stairs. ⸻ Why Guests Love H‑304 “True ski-on/ski-off just steps from the trail” “Quiet, clean, and beautifully maintained” “Huge fireplace after a full slope day” “Beds are comfortable and kitchen has everything you need” • Want to save on your ski trip? Book with us and get great discounts on ski and snowboard rentals - more skiing, more savings! • Pico Mountain is closed on Tuesdays and Wednesdays except during peak holiday periods. Our condo is slopeside at Pico. Killington Resort is a 10 minute drive or quick bus ride. • 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 have smart locks for contactless check in. Your unique access code will be sent the week of your arrival. • Our entire property is non-smoking and non-vaping. You may only smoke or vape outside and 75 feet away from the building. Please properly dispose of all butts. • Quiet hours are from 10pm - 8am. We may 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. • Our condo complex has cameras in the common areas and hallways. There are no cameras in living spaces. • Pets are not allowed. There will be a $750 fine for any unauthorized pets. • You must sign and return our written rental agreement. • EV chargers are available onsite. • The Pico Sports Center is in the same complex as our condo and offers day passes to use the gym and pool facilities. • 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. The Village Square at Pico Condo Association is a family-oriented community primarily used by owners and committed to the peaceful, safe and quiet enjoyment of their residences. While the Association allows rentals and encourages guests to enjoy their visit, they have implemented certain rules related to the use and enjoyment of the units. These rules allow the Association to issue fines and take other actions particularly as it relates to the enforcement of the minimum age requirement of 25, "Quiet Hours" from 9pm until 8am and their no pet policy. The Association will try to resolve issues through the owner or rental agency in the first instance but reserves the right to take action in real time as circumstances require. In short, please respect your neighbors while you are a guest in these condos. SKI RESORTS: Pico Mountain (Ski On/Ski Off - 75 steps to the lifts!), Killington Snowshed Base (6.3 miles), Killington K1 Base (7.0 miles), Mountain Meadows Cross Country Ski and Snowshoe (2.4 miles) BUS: The Bus goes from the condo to Killington Resort every hour. It is $2 to the mountain and free to return. GOLF: Green Mountain National Golf Course (5.4 miles), Killington Golf Course (6.3 miles) NIGHTLIFE: McGrath’s Irish Pub (0.8 miles), Pickle Barrel (4.2 miles), Wobbly Barn (4.7 miles), The Foundry at Summit Pond (3.7 miles) WEDDINGS: The Birch Ridge (4.7 miles), Killington Grand Resort (6.3 miles), Mountain Top Inn & Resort (11.4 miles) AIRPORT: Rutland Regional Airport (15.2 miles), Burlington International Airport (71.2 miles), Albany International Airport (108 miles), Manchester-Boston Regional Airport (119 miles)

Pico Mountain C-307

Killington, VT, US
1 Bedrooms 3 Guests
Aug 25 - 27
$119 night

Welcome to Pico’s Doorstep, your mountain retreat at our one-bedroom, one-bathroom condo in Village Square, nestled slopeside at Pico Mountain in Killington, Vermont. Boasting ski on/off access and just a 10-minute drive (or bus ride) to Killington Resort, this is the perfect spot for ski lovers and mountain adventurers. Our condo features a cozy living room with a comfortable sofa bed, perfect for relaxing after a day on the slopes. The open kitchen is fully equipped to cater to your culinary needs. Retreat to the primary bedroom, featuring a plush queen bed, ensuring a restful night’s sleep. The bathroom is equipped with a tub/shower combo. Stay connected and entertained with WiFi and streaming services, and enjoy the warmth of the fireplace on chilly evenings. Step out onto the patio to bask in the stunning mountain views. For your convenience, EV chargers are available onsite. Plus, take advantage of the nearby Pico Sports Center, offering gym facilities and a pool for your fitness and leisure needs. This condo is your gateway to a memorable stay in the heart of Vermont’s ski country. • Want to save on your ski trip? Book with us and get great discounts on ski and snowboard rentals - more skiing, more savings! • Pico Mountain is closed on Tuesdays and Wednesdays except during peak holiday periods. Our condo is slopeside at Pico. Killington Resort is a 10 minute drive or quick bus ride. • 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 have smart locks for contactless check in. Your unique access code will be sent the week of your arrival. • Our entire property is non-smoking and non-vaping. You may only smoke or vape outside and 75 feet away from the building. Please properly dispose of all butts. • Quiet hours are from 10pm - 8am. We may 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. • Our condo complex has cameras in the common areas and hallways. There are no cameras in living spaces. • Pets are not allowed. There will be a $750 fine for any unauthorized pets. • You must sign and return our written rental agreement. • EV chargers are available onsite. • The Pico Sports Center is in the same complex as our condo and offers day passes to use the gym and pool facilities. • 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. The Village Square at Pico Condo Association is a family-oriented community primarily used by owners and committed to the peaceful, safe and quiet enjoyment of their residences. While the Association allows rentals and encourages guests to enjoy their visit, they have implemented certain rules related to the use and enjoyment of the units. These rules allow the Association to issue fines and take other actions particularly as it relates to the enforcement of the minimum age requirement of 25, "Quiet Hours" from 9pm until 8am and their no pet policy. The Association will try to resolve issues through the owner or rental agency in the first instance but reserves the right to take action in real time as circumstances require. In short, please respect your neighbors while you are a guest in these condos. SKI RESORTS: Pico Mountain (Ski On/Ski Off - 75 steps to the lifts!), Killington Snowshed Base (6.3 miles), Killington K1 Base (7.0 miles), Mountain Meadows Cross Country Ski and Snowshoe (2.4 miles) BUS: The Bus goes from the condo to Killington Resort every hour. It is $2 to the mountain and free to return. GOLF: Green Mountain National Golf Course (5.4 miles), Killington Golf Course (6.3 miles) NIGHTLIFE: McGrath’s Irish Pub (0.8 miles), The Rivershed (3.2 miles), Pickle Barrel (4.2 miles), Wobbly Barn (4.7 miles), Mary Lou’s (5.3 miles), The Foundry at Summit Pond (3.7 miles) WEDDINGS: The Birch Ridge (4.7 miles), Killington Grand Resort (6.3 miles), Mountain Top Inn & Resort (11.4 miles) AIRPORT: Rutland Regional Airport (15.2 miles), Burlington International Airport (71.2 miles), Albany International Airport (108 miles), Manchester-Boston Regional Airport (119 miles)

The Currier Crossing

Killington, VT, US
4 Bedrooms 8 Guests
Aug 25 - 27
$254 night

Welcome to The Currier Crossing, a warm and welcoming 4-bedroom, 3-bathroom home nestled in the heart of Killington, Vermont. Perfect for family getaways and group adventures, this two-level mountain retreat combines cozy charm with modern amenities just minutes from Killington Resort. Spread out across 2,800 square feet, guests enjoy an open-concept kitchen and dining area, a comfortable living room with a wood-burning fireplace, and a well-stocked kitchen featuring a dishwasher, coffee maker, blender, and all essential cookware. Ideal for families, The Currier Crossing includes a travel crib, stair gate, children’s books and games, plus fast WiFi and smart TVs for evening entertainment. After a day on the slopes or nearby hiking and biking trails, unwind with a game of foosball, cozy up by the fire, or enjoy a BBQ on the private deck. A mudroom offers plenty of space for gear, and firewood is provided for guest use. Sleeping arrangements include two queen bedrooms, one double, and two twin beds, comfortably sleeping 8 guests with all linens and towels provided. Three full bathrooms include a tub and shower setup, hair dryers, and essentials. The home is dog-friendly for up to two well-behaved dogs. Guests also receive exclusive discounts on ski and snowboard rentals. Located in a quiet forest setting, The Currier Crossing offers easy access to Killington’s best outdoor attractions including skiing, mountain biking, golfing, and snowmobiling. Enjoy the perfect balance of mountain adventure and peaceful relaxation. Book your stay today and create unforgettable family memories in Vermont.

Powder Run

Pittsfield, VT, US
3 Bedrooms 6 Guests
Aug 25 - 27
$206 night

POWDER RUN: SMART 3BR BASECAMP W/ HOT TUB, AC, EV CHARGER & FLAT PARKING SKIP THE RESORT TRAFFIC. Positioned exactly on the Killington-Pittsfield border, Powder Run offers the easiest winter logistics in the area. This renovated 2,100 sq. ft. home removes the stress of travel: pull into the large flat parking area (no icy driveway drama), plug into the dedicated Level 2 EV charger, and drop your gear in a mudroom equipped with commercial boot dryers. You are ten minutes from the lifts but lightyears away from the noise of the crowded condo complexes. DESIGNED FOR THE APRES SQUAD. The lower patio features a private six-person hot tub that is professionally maintained for your arrival. Upstairs, the open-concept Great Room creates a central gathering point with coffered wood ceilings and a red enamel gas stove. The kitchen is built for real cooking, featuring quartz counters, stainless appliances, and sharp knives. In warmer months, mini-split AC units in every room ensure you sleep cool. FLEXIBLE LAYOUT FOR 8 GUESTS. We designed the sleeping zones to give everyone their own space. Adults can retreat to the Queen bedroom or pick from the spacious Bunk rooms, all featuring clean hardwood floors. The younger crew gets their own territory in either of the Bunk Room (Twin-over-Full with safe integrated stairs) or the Flex Room, which doubles as a media lounge with convertible futons and a TV. Every room is equipped with mini-split AC for rare summer comfort. LOCAL EXPERTS & TICKET DEALS. We are a professional local team, living here year-round to support your stay. Booking this property gives you access to our Curated Local Guide, plus preferred access to ski/board rental savings and limited lift ticket deals through our partners. NOTES • Shared Access: You share the driveway/parking with our neighbor, Peak Hill Home, but your deck and hot tub are strictly private. • Large group? Ask us about booking both homes to sleep 14. HOUSE RULES & FEES • Hot Tub: Included free for peak ski weekends (late Dec to mid-March). Optional $95 setup fee for all other dates. • Quiet Hours: Strictly enforced from 10:00 PM to 8:00 AM. • Occupancy: Max 8 guests. No parties. • Smoking/Pets: Strictly no pets. No smoking/vaping inside or within 75ft ($500 fine). • Exterior Cameras: For safety, cameras are located on the exterior corners of the home. There are no cameras in living areas. • Safety: No fireworks. Guests must e-sign rental agreement.

The Burrow- Near Pico, Hiking, Spacious!

Mendon, VT, US
3 Bedrooms 8 Guests
Aug 25 - 27
$154 night

The Burrow- Bright and spacious 3-bedroom home with a large loft, full kitchen, open living area, and floor-to-ceiling windows that fill the space with natural light. Two full baths, great ski storage at the entry, and plenty of room for families or groups. The loft offers an extra lounge space plus two queen beds. Enjoy the large deck with a grill—perfect for relaxing after a day on the mountain. This three-bedroom home is the perfect place to settle in, spread out, and enjoy your time in Killington. When you first walk in, you’ll notice the roomy entryway with plenty of space to stash skis, boots, and all your gear — super convenient after a day on the mountain. Head upstairs to the main level and you’ll find an open, easy-going layout designed for relaxing together. There’s a full bathroom on this floor, a comfortable living area with a dining space, and a fully stocked kitchen that’s ready for anything from quick breakfasts to full dinners. The floor-to-ceiling windows bring in a ton of natural light and keep the whole space bright and welcoming. This level also has two bedrooms: • Bedroom 1: Queen bed • Bedroom 2: One twin bed + a twin trundle (great for kids or friends traveling together) Up in the loft — accessed by stairs from the living room — you’ll find a second hangout space, another full bathroom, and two more queen beds. The loft feels open and spacious while still giving everyone a bit of privacy. Off the living and dining area, step out onto the large deck. It’s a great spot to get some fresh air, unwind, or fire up the grill. Overall, this home is comfy, bright, and easy to settle into — plenty of space for families or groups who want a relaxed, convenient home base for their Killington trip.

Peak Hill Home

Pittsfield, VT, US
3 Bedrooms 6 Guests
Aug 25 - 27
$205 night

QUIET, WOODED PROPERTY ON KILLINGTON BORDER, minutes from slopes! Peak Hill is a newly rebuilt ski home on the border of Killington and Pittsfield, Vermont and close to all the activity! This home features three bedrooms, two full bathrooms, living room, kitchen, large deck and outdoor area. Spend a day on the slopes (only 10 minutes away) and come back to cook a meal, relax by the gas stove, or catch a show on the smart TV. Sleeping up to 6 people, this is the perfect holiday choice for your family or group. Step into this inviting mountain retreat where the first floor welcomes you with a spacious mudroom, two cozy bedrooms, and a convenient full bathroom complete with a washer and dryer. Ascend the stairs to the heart of the home, featuring a kitchen and living room adorned with a vaulted ceiling, skylights, and abundant windows that flood the space with natural light. The main living area is a cozy haven boasting a gas stove, a smart TV, and plush sofas and lounge chairs for relaxation. Delight in the fully-equipped open kitchen with quartz countertops, sleek dark stainless steel appliances, and a dining area perfect for enjoying meals together. Connected to the living room is a third bedroom and another full bathroom for added convenience. Step outside onto the expansive deck to revel in breathtaking views of the mountain slopes. Bedding is as follows: - Bedroom 1: Queen - Bedroom 2: Twin over full bunk bed - Bedroom 3: Twin over full bunk bed The outdoor area and surroundings: Home offers outside amenities for all seasons and offers a large flat parking space to accommodate everyone. In SUMMER, FALL and SPRING: - Enjoy the outdoor fire pit and seating area - roast your marshmallows by the fire. - Sip your beverage and play outdoor games in a quiet wooded setting - Soak in the fall foliage and peaceful surroundings - Enjoy the large spacious deck In WINTER: - Store your ski and snowboard in the dedicated storage shed by the front door - Park in the flat parking area right off major Vermont road - Hang your gear in the foyer/mudroom and dry your boots with the provided boot dryer - Warm up by the gas stove OTHER THINGS TO NOTE • Hot Tub: The hot tub is included for the peak ski season weekends (late-December to mid-March). For other periods, there is an optional $95 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. • Peak Hill shares a driveway and parking area with another property - Powder Run. Each house has a dedicated parking for 2+ cars with overflow parking located at the base of the property. • For your safety and ours, we have a camera on each corner of the house. They are not in any of the living areas. • The Killington, Vermont area is the perfect place to get away from it all no matter what season it is. There are tons of outdoor activities including: skiing, snowboarding, hiking, antiquing, golf, swimming, shopping, sightseeing, mountain biking and many more. • We’re located less than 4 miles to the Killington Access Road and 8 miles to the slopes. Two golf courses are within 10 minutes of the house with Green Mountain National only 5 mins away. The town recreation center is just a short distance away and features a swimming pool, soccer field, tennis courts, baseball diamond and playground. You’ll also find plenty of trails, ponds, lakes, swimming holes and quaint Vermont towns a short drive away. • Please be sure that you have entered the correct number of guests as we may have a per-person per-night surcharge to cover expenses. You can contact us for a custom quote before booking. • Our minimum rental age is 25. • We will provide you with door codes for our smart locks 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 75 feet away from the property. There is a $500 fine for smoking in or near the house. • You must e-sign and return our written rental agreement after you complete your booking. • The property is NOISE SENSITIVE. Strict quiet hours must be observed 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. • Pets are not permitted. There is a $750 fine for any unauthorized pets. • 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. • 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 (7.9 miles), Killington K1 Base (8.6 miles), Pico Mountain (6.2 miles) GOLF: Green Mountain National Golf Course (2.9 miles), Killington Golf Course (7.9 miles) DINING / NIGHTLIFE: Pickle Barrel (5.8 miles), Wobbly Barn (6.3 miles), The Foundry at Summit Pond (5.4 miles), Rivershed (4.8 miles) WEDDINGS: Killington Grand Resort (8.0 miles), Mountain Top Inn Resort (14.1 miles) AIRPORT: Rutland Regional Airport (21.2 miles), Burlington International Airport (71.6 miles), Albany International Airport (113 miles), Manchester-Boston Regional Airport (116 miles) We look forward to hosting you!

The Maple Leaf

Killington, VT, US
3 Bedrooms 8 Guests
Aug 25 - 27
$298 night

Spacious 3BR Home Near Killington with Indoor Hot Tub, Fire Pit, and Dual Living Rooms Enjoy a true Vermont getaway in this private vacation home just five minutes from Killington Resort. Surrounded by trees on a quiet lot, this two-level property is ideal for families, couples, or friends looking for space, comfort, and the perfect base after a day on the mountain. The home features a rare indoor hot tub (fee may apply - see below), two full living rooms, and comfortable sleeping for up to eight guests. Whether you’re here for ski season, hiking trails, or fall colors, this home is built for relaxation and flexibility. Guests booking through Vrbo receive exclusive discounts on local ski rentals through trusted partners. Highlights include: - Private indoor hot tub located in its own dedicated room - Two large living rooms with Smart TVs - Wood-burning fireplace in one living room, propane stove in the other - Fully equipped kitchen with stainless steel appliances, microwave, cookware, and coffee maker - Dining area with views of the surrounding forest - Three bedrooms and two full bathrooms: - Bedroom 1: Queen bed - Bedroom 2: Queen and Double beds - Bedroom 3: Full bed, Twin bed, and Bunk bed - Fire pit in the yard - BBQ grill on the deck - High-speed Wi-Fi and in-home laundry - Entryway with space for skis, boots, and gear - Private driveway parking Unlike condos or attached units, this is a standalone home with no shared walls and plenty of space for your group to relax. The layout works especially well for multiple families or guests who want to unwind without feeling crowded. After a day at the resort or on the trails, return to a warm fire, a good meal, and a private hot tub waiting for you. With ski rental discounts, flexible living space, and a location just minutes from the slopes, this home offers comfort and convenience in every season. • 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 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. • Want to save on your ski trip? Book with us and get great discounts on ski and snowboard rentals - more skiing, more savings! • 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 on the outdoor deck. 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 front of the house facing the driveway. There are no cameras inside the house. • Quiet hours are from 10pm - 8am. We may use Minut, smart home technology that measures volume levels throughout the property and allows us to respond to noise nuisances without disrupting your stay. NoiseAware 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. • 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. • 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. • 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 RESORTS: Killington Snowshed Base (6.6 miles), Killington K1 Base (7.3 miles), Pico Mountain (4.9 miles) GOLF: Green Mountain National Golf Course (1.5 miles), Killington Golf Course (6.6 miles) NIGHTLIFE: Pickle Barrel (4.5 miles), Wobbly Barn (5.0 miles), Gondoughla (5.6 miles), The Foundry at Summit Pond (4.0 miles) WEDDINGS: Killington Grand Resort (6.6 miles), Mountain Top Inn & Resort (15.8 miles) AIRPORT: Rutland Regional Airport (19.7 miles), Burlington International Airport (86.4 miles), Albany International Airport (105 miles), Manchester-Boston Regional Airport (124 miles), Boston Logan (170 miles)

10 Mi to Killington | AC | Four-Season Retreat

Mendon, VT, US
2 Bedrooms 5 Guests
Aug 25 - 27
$219 night

Near Hiking, Waterfalls & Mountain Biking | Minutes to Killington & Rutland Nestled in Mendon, VT, this cozy 2BR/1BA condo is surrounded by the stunning Green Mountain National Forest and is a perfect year-round base for adventure. Enjoy skiing, hiking, mountain biking, waterfalls, scenic gondola rides, and vibrant fall foliage. Explore the charming village of Woodstock, covered bridges, local shops, and nearby Quechee Gorge — Vermont’s 'Little Grand Canyon' — all a short scenic drive away. -- THE PROPERTY -- MRT-11153470-001 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 bunk bed (twin/full) INDOOR LIVING - 3 Smart TVs, video game console - Propane fireplace - Dining table, high-top seating - Boot & glove dryer OUTDOOR LIVING - Furnished patio - Dedicated ski locker KITCHEN - Refrigerator, dishwasher, stove/oven, microwave - Cooking basics - Drip coffee maker, toaster - Hot water kettle GENERAL - Free WiFi - Electric baseboard heating, mini-split units in all rooms - Linens/towels, complimentary toiletries FAQ - Quiet hours (10:00 PM-6:00 AM) ACCESSIBILITY - Single-story unit, 1st-floor condo - 2 flights of stairs required to enter PARKING - Designated spot (1 vehicle) -- THE LOCATION -- -Central access to Killington, trails & Vermont destinations 2 mi to Pico Mountain 10 mi to Killington Resort (skiing, biking, gondola rides, hiking) 2–4 mi to Gifford Woods State Park & Appalachian Trail 4 mi to Thundering Brook Falls 8 mi to downtown Rutland (dining, shops, Paramount Theatre, Wilson Castle) 15 mi to Rutland Airport Day trips: Woodstock (covered bridges, shops, dining) & Quechee (dramatic gorge, state park, hiking, river views) -- 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 -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - Please observe quiet hours from 10:00 PM to 6:00 AM ADDITIONAL INFORMATION - This single-story property on the 1st floor requires 2 flights of stairs to enter

Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole

Killington, VT, US
4 Bedrooms 8 Guests
Aug 25 - 27
$164 night

Welcome to Alpine Chalet at Pico Mountain, Killington, VT. This 4-bedroom retreat is perfect for mountain getaways, located just across from the slopes. It features a King bedroom with en suite, two Queen rooms, and a fourth room with a Queen and twin bunk. Enjoy the fully stocked kitchen, dining for 8, a cozy living room with a wood-burning fireplace, a bonus room, and an in-unit washer/dryer. Outside, relax on the deck, use the Weber grill, enjoy the fire pit, corn hole, and unique tree house. Welcome to Alpine Chalet, a stunning vacation retreat located at Pico Mountain in Killington, VT. Set along a beautiful drive with breathtaking mountain views, this charming chalet is just across from the slopes, making it a perfect home base for your alpine adventures. Inside, you’ll find four cozy bedrooms: a King suite with an en suite bathroom, two Queen rooms, and a fourth room with a Queen bed and a twin bunkbed. A second full bathroom serves the remaining bedrooms. The renovated kitchen is fully stocked and opens to a dining area with seating for 8, ideal for shared meals after a day on the slopes. Unwind in the living room by the wood-burning fireplace or spread out in the bonus room, perfect for kids or extra entertainment space. The chalet also offers the convenience of an in-unit washer and dryer. Step outside to enjoy a large deck with Adirondack chairs, a Weber grill, a fire pit, and a corn hole setup for outdoor fun. Don’t miss the unique tree house, offering stunning views of the surrounding mountains. You will have the entire home, driveway and yard to enjoy. The pool, sauna, and gym are all resort amenities provided by the Pico Fitness Center, which is a short drive down the road and through the Pico parking lot! They are open 6:00 a.m.- 8:00 p.m. Monday to Friday and 8:00 a.m. to 6:00 p.m Saturday and Sunday. They provide showers, lockers and a changing room, remember to bring a towel! The pool is by reservation only. We are local if you need us.

Lovely home close to hiking & skiing w/WiFi, firepit, balcony, wood stove, & W/D

Pittsfield, VT, US
3 Bedrooms 9 Guests
Aug 25 - 27
$247 night

With a warm and welcoming atmosphere and a secluded location close to hiking trails and skiing, this beautiful home is going to make for the ideal space for your next getaway with the people you love. Explore the scenic scenery around you together or pack your clubs and hit the fairway after a short drive to White River Golf Course. Try one of the local restaurants before heading back to your vacation retreat to wind down. Inside, the home features three levels of comfort and convenience, the main level boasting an attractive open concept that encompasses the living, dining, and kitchen areas. After a day of hot-weather hiking or some winter action, you can kick back in the living room to catch up with old friends or head into the sitting room to pluck a book off the private library shelves. The kids can spread out some of the provided board games while the wood-burning stove keeps the home nice and toasty. Throw a good record on the turntable then head into the full kitchen to prepare a delicious meal for everyone to savor at the dining table with seating for six. You can use the private gas grill to host those fun outdoor barbecues on the deck. Don’t worry about stains - the private washer and dryer will easily knock out whatever the kids pick up while they eat. Downstairs, you’ll find a spacious entertainment area featuring comfortable furniture, a TV, and a work desk for remote workers with and students to handle those last-minute tasks as this property has recently been upgraded with fiber optic internet. When evening falls, gather everyone around the firepit to toast some S’mores and enjoy an evening of stargazing. THINGS TO KNOW Streaming services are available, but guests must log in using their accounts. This vacation home is not equipped with air-conditioning. Four-wheel drive is highly recommended to access the home during winter months. Parties and loud noise are not permitted. Vermont Meals and Room Tax Number: MRT-11472019

CubsCorner - Pool, Sauna, Gym, Close to Mountain!

Killington, VT, US
1 Bedrooms 4 Guests
Aug 25 - 27
$102 night

Welcome to CubsCorner, a 1-bed short-term rental in Killington’s RobinWood neighborhood, minutes from Pico Mountain and 7 from the Killington base. Fully renovated, it features a fireplace, quartz counters, and a stylish bathroom. The queen bed with premium linens ensures a restful stay. The kitchen is fully stocked, and a murphy bed for additional guests. Relax in the spacious living room with a 55-inch Roku TV. Book now for a Vermont retreat! Welcome to CubsCorner, your charming 1-bedroom vacation rental nestled in the heart of the picturesque RobinWood neighborhood in Killington, Vermont. This cozy retreat is strategically located, providing you with easy access to both Pico Mountain, just across the street, and the Killington base, a mere 7-minute drive away. CubsCorner is a haven for outdoor enthusiasts, as it’s just a 3-minute walk from the famed Long Trail and Appalachian Trail, offering breathtaking hiking opportunities right at your doorstep. After a day of adventure, return to the comfort of this fully renovated home that seamlessly combines modern amenities with the warmth of a mountain retreat. Step inside to discover a beautifully redesigned space featuring quartz countertops, a welcoming fireplace, and a bathroom adorned with elegant tiled finishes and a sleek glass shower. The bedroom beckons with a sumptuous queen bed dressed in luxury linens, ensuring a restful night’s sleep. For those who enjoy culinary endeavors, the fully stocked kitchen awaits your culinary creations. Whether you’re preparing a hearty breakfast before hitting the slopes or whipping up a cozy dinner after a day of exploration, you’ll find everything you need at your fingertips. CubsCorner is designed to accommodate additional guests with a murphy bed in the living room. The spacious living area invites relaxation, boasting a 55-inch TV equipped with Roku guest mode streaming. Unwind in style as you catch up on your favorite shows or plan your next day’s adventures. Whether you’re seeking a romantic getaway or a solo mountain retreat, CubsCorner in Killington, VT, provides a perfect blend of comfort, convenience, and natural beauty. Make your short-term stay memorable in this thoughtfully curated home away from home. This is the lower level apartment of a stand alone home. The owner occasionally uses the home as a vacation home. There is a separate entrance to the unit and the driveway is shared, but parking is on one side for this unit. We are local if you need us. The pool, sauna, and gym are all resort amenities provided by the Pico Fitness Center, which is a short drive across the road. They are open 6:00 a.m.- 8:00 p.m. Monday to Friday and 8:00 a.m. to 6:00 p.m. Saturday and Sunday. They provide showers, lockers and a changing room, remember to bring a towel! The pool is by reservation only.

Winter Brook

Killington, VT, US
3 Bedrooms 8 Guests
Aug 25 - 27
$269 night

Renovated Winter Brook Retreat | AC | Peaceful Brookside Setting Your stay includes two complimentary day passes to the Killington Rec Center pool, complete with a diving board. Nestled on a quiet knoll beside a babbling brook, this fully renovated Winter Brook retreat offers a peaceful setting close to all of Killington’s year-round adventure. The home features a beautiful new kitchen, wood floors, luxurious updated bathrooms, and stylish new furnishings. The open-concept living area is ideal for gathering with family and friends, especially around the wood-burning stove after a day on the slopes. On the main floor, one bedroom includes a bunk bed with a full bed below and twin bed above, while the second offers a queen bed; both share a remodeled full bath. Upstairs, the spacious loft features a king bed and a well-appointed primary bath with a garden tub and separate shower. A heat-pump system provides reliable comfort year-round, keeping the home warm in winter and cool in summer. Killington Golf Course and Green Mountain National Golf Course are both just minutes away. Please note: A caretaker resides in the lower-level apartment. Killington offers outstanding skiing and riding for every ability, plus snowmobile tours, tubing, ice skating, and a lively après-ski scene with favorites such as the Wobbly Barn, Pickle Barrel, and Jax’s. Come enjoy a relaxing Vermont getaway and create memories that will last a lifetime. • 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 bird sanctuary.

Near Hiking Trails & Ski Resorts: Killington Home!

Killington, VT, US
3 Bedrooms 8 Guests
Aug 25 - 28
$334 night

Pets Welcome w/ Fee | In-Unit Washer + Dryer | Seasonal Deck & Fire Pit Tucked away in Killington, this 3-bedroom, 2.5-bath home provides a cozy atmosphere and convenient location! Venture out in the winter to hit the slopes at Pico Mountain Ski Resort. In the warmer months, enjoy fishing, hiking, and biking in Green Mountain National Forest and Gifford Woods State Park. After, curl up by the wood-burning stove for a cozy night in or fire up the grill and dine on the deck. -- THE PROPERTY -- MRT-11153470-001 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 king bed - Bedroom 3: 2 twin bunk beds HOME FEATURES - 4 Smart TVs - Wood-burning stove (firewood provided) - 8-person dining table - 4-person breakfast bar - Seasonal deck w/ seating - Seasonal backyard w/ fire pit - Gas grill (propane provided) - Dog bed & dishes KITCHEN - Dishwasher, stove/oven, fridge, stainless steel appliances - Drip coffee maker (starter coffee provided) - Crockpot, microwave, toaster, blender, ice maker, water filter - Dishware/flatware, spices, basic cooking essentials GENERAL - Free WiFi - Central A/C & heating, ceiling fans - Washer & dryer, laundry detergent - Towels/linens, hair dryer - Trash bags/paper towels FAQ - Pet fee (paid pre-trip) - 1 exterior security camera (facing out) ACCESSIBILITY - 2-story home, 2 steps to enter PARKING - Gravel driveway (3 vehicles) -- THE LOCATION -- - 0.7 miles to Pico Mountain Ski Resort - 1 mile to Appalachian Trail Crossing - 3 miles to Green Mountain National Forest & Gifford Woods State Park - 23 miles to Marsh-Billings-Rockefeller National Historical Park - 28 miles to Silver Lake State Park -15 miles to Rutland Southern Vermont Regional Airport -- 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 -- - No smoking - Pet friendly w/ $125 fee per stay (+ fees & taxes, 2 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - Your safety matters. This property features 1 exterior security camera located on a tree in the front of the property, facing the front entrance. It does not look into any interior spaces. The camera records video and sound when activated by motion - This 2-story home requires 2 steps to enter - The deck, backyard, and additional outdoor amenities are available seasonally

Jack S’Bearo- AC, Pool, Mountain Views, Hiking, Gym

Killington, VT, US
1 Bedrooms 4 Guests
Aug 25 - 27
$89 night

Ahoy, ski enthusiasts! "Jack S’Bearo" - a renovated 1-bed, 1-bath on Pico Mountain, VT, offers an exhilarating ski experience steps from the lift and a shuttle to Killington Resort. The new kitchen, wood-burning fireplace, and balcony make it a haven for relaxation. This ski on/ski off treasure boasts a cool design for easy access to the slopes. Grab your gear from the ski locker, step outside, and set sail to the lifts. Make "Jack S’Bearo" your pirate’s cove, where adventure meets comfort! Ahoy, ski enthusiasts! Welcome to "Jack S’Bearo," your swashbuckling sanctuary on Pico Mountain in Killington, VT. This fully renovated one-bedroom, one-bathroom condominium offers an exhilarating ski experience just steps from the lift, with a shuttle service to boot, ensuring a seamless journey to the legendary Killington Resort. Embark on a treasure trove of delights as you enter this meticulously updated unit. A newly minted kitchen, equipped with top-notch appliances designed specifically for this space, awaits to be the galley where you prepare hearty feasts fit for a pirate crew. The wood-burning fireplace adds a touch of nautical warmth, perfect for recounting the day’s adventures on the slopes. "Jack S’Bearo" isn’t just a condo; it’s a fully furnished haven with a bright and welcoming atmosphere from the moment you set foot on board. This ski on/ski off vessel allows you to navigate the slopes effortlessly. Take the elevator or climb the stairs to the first deck, grab your gear from the dedicated ski locker, and step outside—just a pirate’s walk away from the lifts. The sleeping quarters are fit for a captain! The king size bed is made with 600 thread count cotton sheets and there is a desk in the living room that is a murphy bed with a full size bed with a real mattress - so much better than a pull out couch or below deck hammock! Picture yourself on the balcony, raising a tankard to the breathtaking mountain views, surrounded by the crisp Vermont air. This condo promises an unforgettable experience, where the spirit of adventure meets the comfort of home. So, weigh anchor and set your course for "Jack S’Bearo," where every stay is a tale of mountainous excitement and cozy retreats. Arrr, don’t miss the chance to make this pirate’s cove your temporary abode! You will have full access to the condo. We are local if you need us. The Village Square at Pico Condo Association is a family-oriented community primarily used by owners and committed to the peaceful, safe and quiet enjoyment of their residences. While the Association allows rentals and encourages guests to enjoy their visit, they have implemented certain rules related to the use and enjoyment of the units. These rules allow the Association to issue fines and take other actions particularly as it relates to the enforcement of the minimum age requirement of 25, "Quiet Hours" from 9pm until 8am and their no pet policy. The Association will try to resolve issues through the owner or rental agency in the first instance but reserves the right to take action in real time as circumstances require. In short, please respect your neighbors while you are a guest in these condos. The pool, sauna, and gym are all resort amenities provided by the Pico Fitness Center, which is a short walk or drive across the parking lot. They are open 6:00 a.m.- 8:00 p.m. Monday to Friday and 8:00 a.m. to 6:00 p.m. Saturday and Sunday. They provide showers, lockers and a changing room, remember to bring a towel! The pool is by reservation only.

Pico C103

Killington, VT, US
1 Bedrooms 4 Guests
Aug 25 - 27
$125 night

Pico C103 Cozy Condo Steps from the Lifts at Family Friendly Pico Mountain Pico C103 is perfectly located right at the base of Pico Mountain the ultimate family friendly ski destination. The chairlifts are just a short walk from your door, making it easy to ski out in the morning, come back for lunch, and hit the slopes again for the perfect ski day. This warm and welcoming one bedroom condo is ideal for a weekend getaway. Relax by the fireplace after a day of outdoor adventure or take the short drive to Killington Mountain, just minutes away, to experience even more skiing and the area’s vibrant nightlife. Guests also have access to a coin operated laundry conveniently located on the ground floor, and the shuttle bus to Killington runs right from Pico, so you can enjoy the best of both mountains without the hassle of driving. During your stay, enjoy access to the Pico Fitness Center, where you can work out in the gym, unwind in the sauna, swim laps in the pool, or join a spin or yoga class. The Village Square at Pico Condo Association is a family-oriented community primarily used by owners and committed to the peaceful, safe and quiet enjoyment of their residences. While the Association allows rentals and encourages guests to enjoy their visit, they have implemented certain rules related to the use and enjoyment of the units. These rules allow the Association to issue fines and take other actions particularly as it relates to the enforcement of the minimum age requirement of 25, "Quiet Hours" from 9pm until 8am and their no pet policy. The Association will try to resolve issues through the owner or rental agency in the first instance but reserves the right to take action in real time as circumstances require. In short, please respect your neighbors while you are a guest in these condos. Come experience the best of both worlds the cozy charm of Pico and the excitement of Killington right from Pico C103. 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.

Pico D305

Killington, VT, US
1 Bedrooms 4 Guests
Aug 25 - 27
$125 night

Pico D305 – Ski-In Convenience and Cozy Comfort at the Base of Pico Mountain Welcome to Pico D305, a beautiful one-bedroom condo perfectly located right at the base of family-friendly Pico Mountain. Step outside and hit the slopes — you can ski all day and return to your warm and welcoming condo to relax by the fireplace and unwind. This cozy home features a queen-sized bed in the bedroom and a comfortable living area designed for relaxation after a fun day outdoors. A coin-operated laundry is conveniently located on the ground floor of the building for guest use. Getting around is easy — take the shuttle bus on weekends and holidays directly to Killington’s Snowshed Base Lodge, or drive just a couple of miles to experience Killington’s lively nightlife, restaurants, and entertainment. During your stay, enjoy access to the Pico Fitness Center, offering a gym, sauna, lap pool, and a variety of fitness classes including spin and yoga — perfect for both relaxation and staying active. Please note: This unit does not have air conditioning. The Village Square at Pico Condo Association is a family-oriented community primarily used by owners and committed to the peaceful, safe and quiet enjoyment of their residences. While the Association allows rentals and encourages guests to enjoy their visit, they have implemented certain rules related to the use and enjoyment of the units. These rules allow the Association to issue fines and take other actions particularly as it relates to the enforcement of the minimum age requirement of 25, "Quiet Hours" from 9pm until 8am and their no pet policy. The Association will try to resolve issues through the owner or rental agency in the first instance but reserves the right to take action in real time as circumstances require. In short, please respect your neighbors while you are a guest in these condos. Experience the perfect blend of big mountain skiing and small mountain charm at Pico D305 — your ideal Vermont getaway. • 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.

Vacation Rentals in Chittenden by Amenities & Features

More space, more privacy, more points with every home rental.

What makes Homes & Villas by Marriott Bonvoy a unique home rental experience? Unlike other home rental sites like AirBNB, when you book a vacation rental with Homes & Villas by Marriott Bonvoy you always have the whole place to yourself. Plus, as a member of Marriott Bonvoy, you can earn points towards free nights with every stay.

Vacation Rentals Near Chittenden

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