Large group vacation rentals in Olivebridge, NY

Explore 12 large group vacation rentals, homes, and villas in Olivebridge, NY 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 Air Condition Homes, 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 $145 per night and homes offering up to 7 bedrooms and 5 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.

12 Great for Groups in Olivebridge

Ashokan Acres | Private 125-Acre Retreat • Pond + Hot Tub + Sauna + Trails

Kingston, NY, US
6 Bedrooms 10 Guests
Sep 5 - 7
$1,271 night

Some places make you slow down. Ashokan Acres makes you stop entirely. Set on 125 private acres in the Hudson Valley foothills, this historic stone home is the kind of property that takes a moment to fully absorb. Built during the founding era of the United States, it is one of approximately 50 homes constructed in Marbletown during that period — a detail recognized by the Marbletown Historic Preservation Commission and one that gives the property a weight and character no new build can replicate. Panoramic Catskills views stretch across the horizon. A swimmable pond catches the afternoon light just beyond the patio. Trails wind through your own private land, leading to two seasonal waterfalls you can actually hike to, while a mile of pristine Ashokan Creek frontage — the longest frontage of any property — adds a rare, fishable stretch of water to the experience. There’s a wood-burning sauna, a restored barn repurposed as a gathering space, and an open fire pit where evenings tend to last longer than planned. This isn’t a rental that happens to have outdoor space — the land is the whole point. Inside, the home is as considered as the setting around it. Exposed stone walls and timber beams give the 4,000-square-foot interior a grounded, architectural warmth, while vaulted ceilings and oversized windows flood the living spaces with natural light and frame the landscape like a painting. Two fireplaces add to the atmosphere throughout the home. The kitchen is fully equipped and gourmet-caliber, anchored by a large gas range and outfitted for the kind of meals that call for a big table — and the dining room delivers one. A Sonos stereo system keeps the soundtrack going, and when the mood calls for something more, there’s a piano. Six bedrooms sleep up to 10 across a thoughtful mix of configurations — a king suite, queen rooms, and two bunk-friendly spaces ideal for kids or groups traveling together. Four full bathrooms and a half bath round out the layout, and a game room with a pool table gives everyone somewhere to land between adventures. Outside, the hot tub sits on the patio overlooking the water. The BBQ grill is stocked and ready. The trails — and the waterfalls at the end of them — are yours to explore. Ashokan Acres sits within easy reach of Woodstock, Kingston, and Stone Ridge — each with its own distinct character, from record shops and art galleries to farm-to-table dining and antique hunting. The area draws people who know the Hudson Valley well, and keeps drawing them back. But with 125 acres to roam and a property this complete, leaving feels entirely optional. This is a place that rewards guests who want to genuinely unplug — to trade notifications for birdsong and itineraries for instinct. Come any time of year. The Catskills have a way of being exactly what you need, whatever the season. AvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips. Comprised of quaint towns, each with their own charming main street, upstate New York’s Hudson Valley is famed for its natural beauty and seasonal produce. After all, it was here that inspired an entire artistic movement of Romantic painters who captured the area’s rolling hills, colorful foliage, and pastoral setting. View the landscapes in person by hiking the Catskill Mountains. Then, visit local farms where there’s a lot to pick: apples in the fall, strawberries in the summer, and vegetables in between. Local Attractions: Athens Riverfront Park, Hudson-Athens Lighthouse, Kaaterskill Falls, Olana State Historic Site, Greene County Historical Society, Catskill Animal Sanctuary, Hudson Brewing Company, Dutchman’s Landing Park Home Truths: - This home allows up to 2 pets for a fee; undisclosed pets brought without AvantStay’s approval may result in a $500 fine per pet. - Privacy & Security: Exterior security cameras are in place around the property for your peace of mind. - Nature Immersion: Ashokan Acres is a true wilderness retreat — that means wildlife sightings, the sounds of the forest, and the occasional insect are all part of the experience. Embrace it. - Rural Setting: This property offers a genuine off-grid feel. Connectivity and conveniences will be limited — that’s by design. Come ready to unplug. - Climate: The main house is equipped with central heat and air conditioning. The guest house offers central heat and window AC units for warm-weather stays. - Utility room doors in both structures must be secured - these spaces are NOT intended for guest use. - There is also a pump room area (no door to this space) off the pool table room that is OFF-LIMITS to guests. - The septic system upgrade was completed in June 2026, and there are areas of the yard that are currently going through regrowth. Parking Details: - Parking is available for up to 10 vehicles. --- The room configuration is as follows: Primary Bedroom / King bed Bedroom 2 / Queen bed Bedroom 3 / Twin-over-twin bunk bed Bedroom 4 / Queen bed Bedroom 5 / Queen bed Bedroom 6 / 2 twin beds --- This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. IDs will be requested for verification after booking. All bookings over 28 days require a security deposit. We report and prosecute all Credit Card Fraud. Licence number: STR 2024-02

Kripplebush Hollow - Stone Ridge with Water View

Accord, NY, US
3 Bedrooms 6 Guests
Aug 23 - 25
$303 night

Kripplebush Hollow is a sun-drenched retreat in the heart of the Catskills, located 2 hours from NYC. Set on 3+ private waterfront acres, the cabin has 3 bedrooms and 3 full baths. The house features a wood burning stove, waterfront views, and access to the best hiking and dining in the region. Minnewaska, Mohonk, Arrowood Farms, Hasbrouck House, Westwind Orchard and many more are just minutes away. Kripplebush Hollow is the ideal year-round escape! Meander up scenic Kripplebush Road, winding past historic stone homes, and follow the tree-lined driveway up to the house at Kripplebush Hollow. This newly renovated home has memorable Lyonsville Pond views, and a lush yard enveloped by trees and fauna. The open floor plan with soaring ceilings is flooded with natural light through the wall of windows, which makes for some pretty epic sunsets. Cozy up on the sectional sofa and additional club chair beside the woodstove and make some winter memories. The adjacent dining space is beside the kitchen, which has ample counter space for whipping up an amazing meal. The best part is the chef has uninterrupted views out to the pond. A sliding door leads to a pretty sunroom with comfortable seating around a smart TV offering options for movie night. At the rear of the main level is the first of three bedrooms, a queen-sized corner room overlooking the garden. There is also a full bath with a tub/shower and a laundry room. The second floor, which includes a large main bedroom with angled ceiling, has an en suite bathroom with a walk-in shower and soaking tub looking out at the private garden. Outside the bedroom is a lofted reading nook with an inviting club chair. On the lower level the final bedroom, with two single beds, has pleasing water views. There is a communal space with a couch, a games table, and a large smart TV. Kids will particularly love this spot. A full bathroom with a tub/shower rounds out this floor As for the exterior, there is an expansive deck with lounge seating and a picnic table overlooking the pond. There is also a propane grill available on premise. For your little ones, we also have a pack’n’play and a high chair stored in the first floor closet should you need! Kripplebush Hollow is two hours from New York City, and while you’ll definitely want a car to get enjoy the region. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. There is plenty of parking on the premises. Cooling: The home is equipped with three split units — one on each level of the house. License number: 10863

Epic architectural masterpiece w views hot tub

Accord, New York, US
3 Bedrooms 8 Guests
Aug 22 - 24
$1,004 night

Perfect for “cityfolk” looking for a uniquely sophisticated mountain experience! Imagine escaping from the rush of the city and finding this stunning property amidst peace and tranquility, complete with panoramic mountain views, a cozy wood-burning stove, and a soothing hot tub. It’s perfection! Living Spaces With the fascinating juxtaposition of a cozy mountain cabin and an urban industrial-style loft, this property never ceases to surprise and delight. The living room, featuring a plush sectional sofa, is tucked away in a cozy “cabin” atmosphere, with wood beams overhead and a warm wood-burning stove. The 65” HDTV with Netflix and HBO Max allows for the opportunity for a “Netflix and chill” evening in. Cooking & Dining The industrial-style kitchen comes fully equipped with stainless steel appliances, and a row of windows to allow the sunshine in. A breakfast bar provides additional food prep space and seating for 4. The dining room has the best view in the house! Situated directly in front of the dreamy window wall, you’ll have a completely unencumbered view of the woods and the mountains beyond. This section of the home also boasts a two-story ceiling, so your view is not limited to a traditional roof line. It truly feels like there’s almost nothing between you and the nature scene before you. Sleeping Accommodations and Bathrooms On the first level is a king bedroom with a sleeper sofa. A full bathroom and laundry area is on the other part of the level. The second floor is up a flight of industrial-style metal steps, while overlooking the magnificent wood and mountain view. Here, you’ll find two additional bedrooms, both with queen beds and a full bathroom with a soaking tub. Outdoor Amenities Our guests love to enjoy their surroundings up close and personal in the bubbling hot tub. This area is a nirvana for hikers and outdoor enthusiasts. We are a simple drive from the Catskills, the Ashokan Reservoir, Minnewaska State Park Preserve, and Mohonk Preserve. *Ticks/bugs/bees are a regular part of upstate NY. Some things to note: This home is not suitable for small children as the stair rails are wide. Our property is located in Accord, NY. We are south of the Ashokan Reservoir in the Catskills/Hudson Valley Region. Most of our guests drive to our location, but if you’re flying, the closest airport is Stewart International Airport (SWF / KSWF, about 36 miles from Accord.

Foot Loose | Woodsy Retreat • Fireplace • Near Trails + Wineries

Accord, NY, US
2 Bedrooms 4 Guests
Aug 22 - 24
$245 night

Foot Loose brings that easy Hudson Valley feeling to life — warm wood walls, sunlit windows, and a tucked-away setting that feels made for slow mornings, long dinners, and fresh-air evenings. Set in Accord, this cozy 2-bedroom retreat with a bonus sunroom blends cabin character with relaxed, lived-in comfort, creating a stay that feels inviting in every season. Inside, the main living space is bright, open, and wrapped in natural wood, with vaulted ceilings, skylights, and wide windows that pull the surrounding trees right into the room. The living area offers a soft place to unwind, while the dining table for six sets the scene for shared meals, board games, or lingering over coffee. Just off the main gathering space, the fully equipped kitchen comes stocked with the essentials, making it easy to cook in after a day of hiking, exploring, or browsing nearby farm stands. Step outside and the home opens to a peaceful deck surrounded by greenery. Lounge under the umbrella with a book, enjoy morning coffee in the shade, or settle in for an easy evening as the woods quiet down around you. A nearby fire pit area with Adirondack chairs adds another laid-back spot to gather, giving the outdoor space a true upstate retreat feel. The sleeping setup is flexible and comfortable for up to six guests. The primary bedroom features a queen bed, the second bedroom offers a double bed, and the sunroom includes a daybed for an additional guest, a child, or anyone who wants a bright little corner of their own. A shared bathroom with a shower/tub combo keeps the layout simple and convenient. Located in Accord, Foot Loose puts you close to some of the Hudson Valley’s best-loved experiences. Spend the day hiking at Mohonk Preserve or Minnewaska State Park, exploring New Paltz, visiting local orchards and farm stands, or sampling the region’s wineries, cideries, and small-town restaurants. Here, quiet wooded living and easy access to the area’s highlights come together beautifully. AvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips via concierge@avantstay.com. It’s no wonder city dwellers flock to upstate New York’s Catskill Mountains for a break from the daily grind. Its rural beauty and colorful foliage is a beautiful change of scenery. After all, it was here that inspired an entire artistic movement of Romantic painters to capture the area’s rolling hills and pastoral setting. View the landscapes in person by hiking the Catskill Mountains, and then head to the farm to pick seasonal produce. Think apple picking in the fall and strawberries in the summer! Local Attractions: Arrowood, Westwind Orchard, Inness, O&W Rail Trail, Minnewaska Reserve, Ashokan Reservoir, Babblers at Wylder Windham, Mill Rock, Brandywine, Chicken Run, Zicatela’s, The Tap House, Briars & Brambles Bookstore, GardenHeir, Windham Mountain, Tipp’s Tavern, Jimmy O’Connor’s, Windham Diner, The Country Store, Studio Minimale. Home Truths: - Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without AvantStay’s approval there is a fine of $500 per pet. - This home does not have a dishwasher. Parking Details: - Parking is available for 4 cars. --- The room configuration is as follows: Primary Bedroom / Queen bed Bedroom 2 / Full bed Bonus Room / Daybed --- This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. IDs will be requested for verification after booking. All bookings over 28 days require a security deposit. We report and prosecute all Credit Card Fraud.

Relax in Style at Historic Modern on Main with Modern Amenities & Wooded Views

Stone Ridge, NY, US
3 Bedrooms 6 Guests
Aug 22 - 24
$320 night

Discover the perfect blend of modern comfort and vibrant style in this stunning 3-bedroom home nestled in the heart of Stone Ridge, New York. Surrounded by mature trees and natural beauty, Historic Modern on Main is a beautiful two-story home with a charming flower-lined entrance that sets the tone for your stay. Inside, you’ll find a contemporary interior design that’s both colorful and inviting, featuring bright living spaces that inspire relaxation and connection. The home comfortably accommodates guests with one king bedroom and two queen bedrooms, ideal for families or groups seeking privacy and comfort. Two full bathrooms showcase beautiful, high-end finishes, while an additional half bathroom adds convenience for larger gatherings. The fully equipped kitchen is thoughtfully designed with modern appliances and ample counter space — perfect for cooking and entertaining whether you’re preparing a quick breakfast or a celebratory dinner. Every detail inside this home reflects a commitment to style and functionality, from the spacious living areas to the carefully curated décor that complements the serene wooded surroundings. Whether you’re unwinding indoors or stepping outside to enjoy the peacefulness of the natural landscape, this home offers an ideal retreat after a day of exploring. AvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips! Comprised of quaint towns, each with their own charming main street, upstate New York’s Hudson Valley is famed for its natural beauty and seasonal produce. After all, it was here that inspired an entire artistic movement of Romantic painters who captured the area’s rolling hills, colorful foliage, and pastoral setting. View the landscapes in person by hiking the Catskill Mountains. Then, visit local farms where there’s a lot to pick: apples in the fall, strawberries in the summer, and vegetables in between. Local attractions: Stone Ridge offers easy access to some of the Hudson Valley’s top spots—hike the cliffs and trails of Mohonk Preserve and Minnewaska, explore Woodstock and Kingston’s arts and dining scenes, visit Olana and Opus 40, sip along the Shawangunk Wine Trail, and unwind by the Ashokan and Rondout Reservoirs. Home Truths: - This home allows up to 2 pets for a fee; undisclosed pets brought without AvantStay’s approval may result in a $500 fine per pet. Parking Details: - Driveway parking available for up to 8 vehicles. This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. There is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We’ve enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions. As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards. IDs will be requested for verification after booking. All bookings over 28 days require a security deposit. We report and prosecute all Credit Card Fraud.

’Casa Reál’ ~ Expansive Woodstock House w/ Hot Tub

West Hurley, NY, US
4 Bedrooms 8 Guests
Aug 30 - Sep 2
$578 night

Welcome to 'Casa Reál,' an exquisite 4-bedroom, 4-bathroom ranch vacation rental in the iconic upstate town of Woodstock. This wonderful mid-century home is situated on a semi-private lot with scenic tree views and a hot tub, mere minutes from town, surrounded by towering pines and beautiful landscaping. Inside, find a bright living space, custom drapery, contemporary furnishings, and a gourmet kitchen. Dine al fresco on the oversized screen porch and end the night gathered around the fire pit! -- THE PROPERTY -- Fire Pit w/ Adirondack Chairs | Newly Renovated Kitchen, Bathrooms, & Outdoor Spaces | Baby Grand Piano This unique Woodstock home is a perfect home base for those looking to get outdoors with nearby hiking trails, skiing areas, and local attractions, all located within a day trip of NYC. Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: King Bed | Bedroom 4: Queen Bed OUTDOOR LIVING: Private hot tub, new screened-in porch & skylights, 2-acre lot, Weber gas + charcoal barbecue grills, massive lawn INDOOR LIVING: Mid-century modern furnishings, sunken living room, wood-burning fireplace, formal dining room, all new hardwood floors, white baby grand piano, custom window treatments CHEF'S KITCHEN: Fully equipped & newly renovated (over $70,000) w/ quartz countertops, V-Line 6-burner gas range stove, new wet bar, ice maker & wine cooler, stainless steel appliances, 2 dishwashers, refrigerator w/ icemaker, juicer GENERAL: Washer/dryer, air conditioning, linens/towels, suitable for children, suitable for elderly, pet fee (paid pre-trip) -- THE LOCATION -- SKIING AREAS: Windham Mountain (30 miles), Belleayre Mountain Ski Center (31 miles), Mohawk Mountain Ski Area (58 miles), Thunder Ridge Ski Area (60 miles) OUTDOOR RECREATION: Woodstock Waterfall Park (3 miles), Ashokan Reservoir (6 miles), Overlook Mountain Wild Forest (10 miles), Falling Waters Preserve (12 miles), Minnewaska State Park Preserve (32 miles), fishing, hiking THINGS TO DO: Woodstock Playhouse (2 miles), Stockade District (9 miles), Rondout Lighthouse (12 miles), Vanderbilt Mansion National Historic Site (26 miles), New York City (112 miles) AIRPORT: New York Stewart International Airport (47 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 - Dog friendly with $150 fee (+ fees & taxes, maximum 2 allowed) - No cats allowed - No events, parties, or large gatherings - Additional fees and taxes may apply

Mohonk View - Hot Tub & Beautiful Mountain Views!

Accord, NY, US
3 Bedrooms 6 Guests
Sep 6 - 8
$510 night

Take in the peaceful surroundings of this cozy 3 bed, 3 bath contemporary home in Accord, NY just under 2.5 hours from NYC. Boasting outdoor loungers and a hot tub for a truly relaxing experience, Mohonk View is the epitome of serenity where nature and comfort meet. With large windows throughout the home, the interior is flooded with warm natural lighting creating an inviting atmosphere. Enjoy the enclosed seating and dining area with mountain views and a lush background setting! Tucked away in a private location, Mohonk View remains conveniently close to a wide variety of exciting attractions and outdoor adventures. Nearby towns: Kerhonkson (10mins), Stone Ridge (15mins), High Falls (17mins), New Paltz (30mins), Saugerties (45mins) Mohonk View warmly welcomes its guests with exceptional views as you walk along the beautiful bluestone path, thoughtfully designed to take advantage of the breathtaking landscape and mountain views. With ample outdoor space and a relaxing cedar hot tub, this property promises an unforgettable vacation experience. The living room boasts vaulted ceilings complemented by maple accents and a cozy wood-burning stove creating a spacious and warm ambiance. The fully equipped kitchen is designed for both functionality and style featuring high-end appliances. Just off the kitchen is a spacious screened-in porch which serves as another inviting living and dining area. This versatile space truly shines as an ideal spot for entertaining guests or enjoying a peaceful morning coffee while immersed in nature’s beauty. Enjoy the uninterrupted views of the surrounding mountains and appreciate the beauty of the changing seasons throughout the year. Nestled to one side of the house the master bedroom has high ceilings, a TV, en suite bathroom and sliding glass doors allowing for plenty of natural light and stunning views. The deck outside the master bedroom is the ideal spot for yoga sessions or lounging with a good book. The second bedroom has a queen sized bed with a dedicated working space and a bathroom next door. Designed with kids in mind, the third bedroom features bunk beds and large windows that fill the room with light. This property immerses you in nature while providing the comforts of home, perfect for relaxation. As you sip your morning coffee with a stunning view or settle in for an evening under the stars, savour the balance of rustic charm and modern amenities. Mohonk View is 2 hours and 15 minutes from New York City. A car is essential for getting there and exploring the area. The main access routes are the New York State Thruway (I-87) and Route 17. We strongly recommend a 4x4 or a car with four-wheel drive, especially in winter, to handle snow and gravel roads.

Trail’s End - Modern and Private Cabin in the Wood

Kerhonkson, NY, US
2 Bedrooms 4 Guests
Aug 23 - 25
$336 night

Escape to Trail’s End, a beautifully designed and modern cabin in the picturesque Hudson Valley, less than 2.5 hours from NYC. This newly built 2-bed, 1-bath cabin blends modern comforts with the simplicity of the countryside. Set on just under 2 acres, enjoy floor-to-ceiling windows, a cozy wood-burning stove, a sleek kitchen, a luxurious bathroom with dry sauna, and a fire-pit outside. Nearby towns: Kerhonkson(20mins), Stone Ridge(20mins), Accord(25mins), & Kingston(40mins) As you step inside, you are greeted by an airy open-plan design, where floor-to-ceiling windows flood the space with natural light, offering breathtaking views of the surrounding landscape. The living area beckons with its cozy ambiance, complete with a wood-burning stove and a flat-screen TV, perfect for unwinding after a day of exploration. The sleek and fully equipped kitchen boasts modern amenities, including a built-in cooktop and oven set amidst elegant black tiles and countertops. Adjacent to the kitchen, a spacious dining area with seating for six invites you to savor shared meals while soaking in the stunning vistas through the oversized windows. With two comfortable bedrooms featuring plush queen beds and large window/doors providing seamless access to the outdoors, Trail’s End ensures a restful night’s sleep immersed in nature. The luxurious bathroom offers a large standing shower and dry sauna. Outside, on nearly 2 acres of land, you’ll find a fire pit where you can gather under the stars, surrounded by the tranquility of the natural surroundings. Venture beyond the cabin, and you’ll discover a wealth of attractions in the area. Explore the nearby Vernooy Kill State Forest, home to the enchanting Vernooy Kill Falls and Swim Hole, offering opportunities to reconnect with nature. Situated between the Route 209 and Route 28 corridors, Trail’s End provides easy access to a multitude of outdoor activities, from hiking and rock climbing at Mohonk Mountain and Minnewaska State Park to skiing and snowboarding along the Rt. 28 corridor. Whether you’re seeking adventure or simply craving a peaceful retreat, Trail’s End offers the perfect balance of modern elegance and rustic charm, ensuring a truly rejuvenating countryside escape. Trail’s End is about 2.5 hours from New York City and guests can travel around by car as it is a rural area with limited public transportation. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. License number: 11777

Abbey Road Farmhouse - Pool, Firepit and Stunning Views

Mount Tremper, NY, US
7 Bedrooms 14 Guests
Aug 22 - Sep 21
$295 night

Nestled in the heart of tranquil upstate New York, Abbey Road Farmhouse offers an idyllic escape just 2.5 hours from NYC. With ample space for up to 14 guests, the main house boasts 5 beds, 3.5 bath, a cozy living room, modern kitchen, office & gym. A charming 2-bed, 2-bath cottage includes a full kitchen, living room and private deck. Outside enjoy the pool(seasonal), outdoor dining, firepit, & expansive backyard. Nearby towns: Phoenicia (5 mins), Woodstock (25 mins), and Hunter (25 mins). As you step into the main house, you are greeted by an ambiance of warmth and hospitality. The spacious living room, adorned with large windows framing picturesque views, invites you to unwind by the cozy fireplace or sink into the plush couch while enjoying your favorite shows on the TV. The adjacent modern kitchen, complete with a large island and top-of-the-line appliances and everything you need to whip up delicious meals for your loved ones. And for those who need to catch up on work, a convenient office space awaits with a desk and comfortable chair. Retreat to the well-appointed bedrooms, where tranquility and comfort merge seamlessly. The main house boasts a variety of sleeping arrangements to suit every guest’s needs, including a king bed, three bedrooms with queen beds, and the fifth bedroom with two twin beds. With three bathrooms and an additional powder room, convenience and privacy are ensured for all. Indulge in a rejuvenating soak in the luxurious bathtub, or sink into plush bedding for a restful night’s sleep amid the serene countryside surroundings. Venture outdoors to discover a paradise of leisure and recreation. A sprawling deck hosts a glistening pool(seasonal and sun loungers. Gather around the fire pit for conversations under the stars or dine alfresco on the stone deck. Enjoy the views overlooking the meticulously landscaped gardens, framed by charming stone walls and white fences, offering a picturesque backdrop for cherished memories. The front deck’s rocking chairs are perfect for moments of tranquil contemplation. Nestled beside the main house, the quaint and charming cottage offers cozy and inviting spaces. Relax in the sitting area, featuring large windows and a wood-burning stove for extra warmth. Step onto your private deck with outdoor seating to enjoy the peaceful surroundings. The living room provides plenty space for relaxation and entertainment, with a large TV above the fireplace. A convenient work station is available for staying connected. Two bedrooms with queen beds offer a restful retreat, while two full bathrooms includes a tub and shower combo. Escape to Abbey Road Farmhouse, where every corner is a testament to tranquility, comfort, and cherished moments with loved ones. Experience the allure of upstate living at its finest, where memories are made and dreams are realized. Abbey Road Farmhouse is just about two and a half hours from New York City, and you’ll definitely want a car to get there and around the area. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. * Please note that the pool is available during the summer season only. Please inquire regarding opening and closing dates. *Note: the pool does not have a ladder to get in and out, or stairs.* * The Main House has central A/C. The Cottage has window units in each bedroom in the summer. License number: 11788

Quaint Woodstock Escape - 2 Mi to Tinker St!

West Hurley, NY, US
3 Bedrooms 6 Guests
Aug 23 - 25
$456 night

Highlighted by its spacious grounds and close proximity to restaurants, entertainment, and shopping, this secluded Woodstock retreat is well-equipped for relaxation and fun. This 3-bedroom, 2-bathroom vacation rental features a convivial common area with a Smart TV and 2 fireplaces, as well as a fire pit to gather around when it’s time to unwind. In addition to nearby hiking trails and fishing, nature lovers can enjoy spotting deer and other wildlife in the open fields surrounding the house! -- THE PROPERTY -- Fire Pit | Eat-In Kitchen | 2 Brick Fireplaces This charming home is perfect for small families and groups of friends to enjoy a quiet stay in Woodstock with easy access to local attractions. Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bed INDOOR LIVING: Smart TV, 2 family dining tables, cable/satellite TV, laptop-friendly work area, vaulted ceilings, exposed beams OUTDOOR LIVING: Spacious yard, charcoal grill, patio w/ outdoor dining area, Adirondack chairs KITCHEN: Cooking basics, stainless steel appliances, dishwasher, stove/oven, microwave, coffee maker GENERAL: Free WiFi, linens/towels, washer/dryer, complimentary toiletries, central heating, ceiling fans, window A/C units, laundry detergent, trash bags/paper towels FAQ: 2 steps required to access, 1 bedroom & 1 bathroom on 1st floor, 2 additional long-term rentals on-site PARKING: Driveway (3 vehicles) -- THE LOCATION -- TINKER STREET (2.0 miles): Woodstock’s Main Street featuring restaurants, shops, playhouses, art galleries, flea market, and boutiques OUTDOOR FUN: Woodstock Golf Club (1.6 miles), Woodstock Waterfall Park (2.2 miles), Ashokan Rail Trail (2.5 miles), Overlook Mountain Trailhead (4.6 miles), Forsyth Nature Center (8.6 miles), Falling Waters Preserve (11.7 miles), Poets’ Walk Park (12.8 miles), Kaaterskill Wild Forest (17.6 miles) ART + ENTERTAINMENT: Woodstock Playhouse (1.6 miles), Colony (2.1 miles), Levon Helms Studio (2.7 miles), Brydcliffe Theatre (3.9 miles), Opus 40 (6.5 miles), The Center for Photography at Woodstock (9.6 miles) EATS + DRINKS: Cucina (1.5 miles), R&R Taproom (1.6 miles), The Mud Club (1.9 miles), Bread Alone Bakery (2.0 miles), Tinker Taco Lab (2.1 miles), Station Bar & Curio (2.3 miles) MUSEUMS: Woodstock Artists Association & Museum (2.1 miles), Hudson River Maritime Museum (10.9 miles), Trolley Museum of New York (10.9 miles) AIRPORTS: Hudson Valley Regional Airport (41.6 miles), New York Stewart International Airport (47.4 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 - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property has 1 bedroom and 1 bathroom on the 1st floor, but an internal flight of stairs is required to access the upstairs bedrooms and bathroom - NOTE: There are 2 additional units on-site occupied by long-term renters, other guests may be present during your stay

Charming Cottage w/ Yard - 2 Mi to Tinker St!

West Hurley, NY, US
2 Bedrooms 4 Guests
Aug 22 - 24
$334 night

Take a break from the chaos of city life and head to the quaint village of Woodstock, where this cozy vacation rental awaits your stay. Nestled in the Catskills Mountains, this 2-bedroom, 1-bath cottage promises a peaceful escape with a patio, grill, and fire pit outside and homey furnishings with ample bohemian charm inside. When you’re ready to wander off, indulge in the art, music, and eats of Tinker St or immerse yourself in nature’s beauty at Overlook Mountain or Kaaterskill Wild Forest! -- THE PROPERTY -- Furnished Patio | Charcoal Grill | Washer/Dryer A tranquil retreat awaits you and your family in the Catskills, where this delightful cottage places you in proximity to the best hikes, shops, and restaurants in Woodstock. Bedroom 1 (1st Floor): Queen Bed | Bedroom 2 (2nd Floor): Queen Bed OUTDOOR LIVING: Large yard w/ wooded views, private patio w/ fire pit, picnic table, grill KITCHEN: Fully equipped, cooking basics, drip coffee maker, 2-person breakfast bar, 4-person dining table INDOOR LIVING: Smart TV, ceiling fans, designated workspace in Bedroom 1, walk-in closets GENERAL: Free WiFi, central heating & A/C, complimentary toiletries, linens/towels, laundry detergent ACCESSIBILITY: 2-story home, step-free entry, bedroom/bathroom on 1st floor PARKING: Gravel driveway (3 vehicles) -- THE LOCATION -- TINKER STREET (2.0 miles): Woodstock’s Main Street featuring restaurants, shops, playhouses, art galleries, flea market, and boutiques OUTDOOR FUN: Woodstock Golf Club (1.3 miles), Woodstock Waterfall Park (2.2 miles), Ashokan Rail Trail (2.3 miles), Forsyth Nature Center (7.7 miles), Overlook Mountain (9.8 miles), Falling Waters Preserve (11.7 miles), Poets’ Walk Park, Kaaterskill Wild Forest (17.9 miles) ART + ENTERTAINMENT: Woodstock Playhouse (1.7 miles), Colony (2.1 miles), Center for Photography (2.1 miles), Levon Helms Studio (2.8 miles), Brydcliffe Theatre (3.9 miles), Opus 40 (6.5 miles) EATS + DRINKS: R&R Taproom (1.6 miles), Cucina (1.6 miles), The Mud Club (1.9 miles), Bread Alone Bakery (2.0 miles), Tinker Taco Lab (2.1 miles), Station Bar & Curio (2.3 miles) MUSEUMS: Woodstock Artists Association & Museum (2.1 miles), Hudson River Maritime Museum (10.9 miles), Trolley Museum of New York (10.9 miles) AIRPORTS: Hudson Valley Regional Airport (42.5 miles), New York Stewart International Airport (47.4 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: Although this property offers step-free entry with a bedroom and bathroom on the main floor, interior stairs are required to access the 2nd-floor bedroom

Family Home w/ Outdoor Oasis in Hudson Valley

High Falls, NY, US
3 Bedrooms 9 Guests
Sep 1 - 3
$364 night

Tree-Lined Property on 1 Acre | 3 Mi to Hiking Trails Step into laid-back adventure at this High Falls vacation rental — perfect for families and friend groups chasing Hudson Valley fun. The 3-bed, 2-bath home invites you to unplug and unwind, whether you de-stress in the sauna, dine on the deck, or curl up by the wood stove. Feeling inspired to explore? View fall foliage at Minnewaska State Park or stroll the Walkway Over the Hudson. Upstate memories await! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 twin bunk bed w/ twin trundle - Additional Sleeping: 1 portable crib INDOOR LIVING - Board games & books, children's toys - Wood-burning stove - Dining table - 2 desks OUTDOOR LIVING - Deck w/ retractable shades & string lights - Outdoor sofa, outdoor dining set - Backyard, playground set - Sauna (waiver required) - Front deck w/ bistro set KITCHEN - Dishwasher, refrigerator, stove/oven, microwave - Drip coffee maker & Italian press - 4-slice toaster, toaster oven - High chair - Cooking basics, dishware & flatware, trash bags & paper towels GENERAL - Central heating & A/C - Washer & dryer - Towels & linens provided. - Free Wi-Fi FAQ - 2 exterior security cameras (facing out) ACCESSIBILITY - Single-story home - 6 steps to enter at front door, 3 steps to enter at backdoor PARKING - Driveway (4 vehicles) -- THE LOCATION -- - Near hiking & biking trails, rock climbing - 3 miles to Mohonk Preserve - 8 miles to New Paltz: Historic Huguenot Street, restaurants & cafes, shops - 7 miles to Minnewaska State Park Preserve - 13 miles to Kingston, 22 miles to Woodstock - 14 miles to Ashokan Reservoir - 18 miles to Walkway Over the Hudson State Park - 34 miles to New York Stewart International 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 - No pets allowed - No events, parties, or large gatherings - Must be at least 18 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story home requires 6 steps to enter at the front entrance and 3 steps to enter at the rear entrance - A waiver is required prior to using the sauna - Your safety matters. This property features 2 exterior security cameras. Camera 1 is on the front door facing the front entry, and camera 2 is on the back door facing the back entry. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion

Vacation Rentals in Olivebridge 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 Olivebridge

Saved Home Image
Sign in or join now to view and save the homes you love