House holiday rentals in Woodstock

The exterior of the cottage is shown, featuring rich wood paneling and large glass doors. A stone pathway leads to a charming seating area, which includes a decorative bench. Lush greenery surrounds the property, enhancing the natural environment.

4.91 out of 5 average rating, 783 reviews

Dutch Touch Woodstock Cottage

The Dutch Touch captures the best Woodstock has to offer. Be in the Village and secluded at the same time! This Woodstock treasure is surrounded by gardens, with Monet-worthy views, peaceful mountains and swaying pines. It’s your cozy and peaceful home away from home, yet only a short, pretty walk to the very center of the village. Dutch Touch is the "brain-child" of artist, Manette van Hamel, an early Woodstock arts colony resident whose work is held in the permanent collection of the Met. The kind of place one would expect an artist to build: Perfect for a romantic get-a-way or solo retreat. Recline on your own deck beside a sparkling stream, soak up the sun, read a good book, or walk into town and visit the galleries and shops, or zip up the mountain for hikes, a visit to the Buddhist Monastery or a tour of the Byrdcliffe arts colony. Winter visitors will love the open fireplace, and the fresh winter scent of forest, hearth and home.

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The living and dining area features a combination of natural light and stylish furnishings. A warm wood dining table is surrounded by green chairs, while a cozy seating arrangement includes a leather couch and a unique wood slab coffee table. The space is enhanced by greenery from houseplants.

4.96 out of 5 average rating, 135 reviews

Maple House: Private/Romantic Walk-to-Town Oasis

Treat yourself to a romantic getaway or relaxing retreat in your own newly-renovated historic farmhouse, ideally located on a quiet dead-end lane just 1 block from the Woodstock Village Green ~ the heart of this famous “colony of the arts”. You can walk to restaurants, cafes, galleries, boutiques, theaters, clubs... Or you can stay home and relax in your private oasis of peace and beauty with a fully-fenced landscaped backyard, fireplace, chef’s kitchen, heated soaking tub, and luxury amenities.

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A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

4.94 out of 5 average rating, 398 reviews

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

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The farmhouse exterior features a spacious porch with steps leading down to a grassy area. The surrounding landscape includes trees, providing a natural setting. Large windows allow for plenty of natural light, enhancing the home's open feel.

4.91 out of 5 average rating, 312 reviews

Beautiful farmhouse with Mountain View- HITS- AC

Beautifully renovated 3 bedroom, 1.5 bath farmhouse on 3 acres. Close to Saugerties, Woodstock and Hunter Mountain yet with a large property and Mountain View! 4 minutes to HITS horse show! Close to Skiing! *NEW in 2025- Air Conditioning with mini splits throughout the home! The Hudson Valley has a lot to offer and we hope our home can be your cozy retreat to connect and unwind, cook delicious meals and sleep well as you explore and enjoy the area! Kid Friendly, Playground on the property!

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4.98 out of 5 average rating, 118 reviews

A bright and open living space features a spacious blue sofa and a dining area with a white table surrounded by wooden chairs. Large windows bring in natural light, while a modern kitchen is visible in the background, providing a seamless flow to the outdoor deck.

Home in Mount Tremper

Woodstock Hideaway

Escape to our cozy 3-bedroom, 2.5-bathroom home in the Catskill Mountains! Ideal for families, couples, or friends seeking a relaxing break. Unwind in front of the fireplace, whip up culinary delights in our chef's kitchen or grill out on the back deck. Relax and enjoy breathtaking mountain views by the firepit. Minutes away from hiking, swimming and ski slopes, offering endless outdoor adventures. Explore nearby Woodstock, known for its entertainment, shopping, and farm to table dining options.

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A light-filled living area features an open concept with a spacious gray sofa adorned with decorative pillows and an orange accent couch. A wooden coffee table occupies the center, while a kitchen with modern appliances is visible in the background. Green plants and framed artwork enhance the inviting space.

4.97 out of 5 average rating, 117 reviews

Stunning Light-filled Home w/HOT TUB walk to town

Standby for photos of our premium upgrades. Spotless home in walking distance to town. Featured in Hudson Valley Style magazine Road Affair's "15 Best Airbnbs in Woodstock" pick 2024. Explore Woodstock & nearby mountains from light-filled 1700 sq ft 1-BR home. Enjoy changing seasons from private patio w/hotub, dining, fire pit & grill 365 days a year. 1st floor fully equipped kitchen, 65" tv, dining room table & desk. 2nd floor bedroom is 800 sq ft & full bathroom & desk 2 dogs w/no fee

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A spacious house is surrounded by trees, showcasing large windows and a red roof. A patio area is visible in front, with a picnic table nearby. The natural landscape includes a grassy yard and distant mountain views, providing a serene outdoor setting.

4.99 out of 5 average rating, 127 reviews

Broadview Retreat House, walk to town

"Broadview Retreat House" is located in Woodstock NY. The house is a 12 minute walk to Tinker Street, the center of town. Enjoy the peaceful mountain views . Great for families with kids. Easy Cancellation Policy. 4 large bedrooms and 2 full bathrooms. Large stocked kitchen. Detailed Host Guidebook with area restaurants, things to do. Contactless check in. Tons of extras included. Entire house to yourself. Vintage Airstream may occasionally house owners. *STR permit #21N-142 Town of Woodstock

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The quaint exterior of the house is framed by lush greenery and flowering shrubs. A stone pathway leads to the front entrance, enhanced by a large window that allows natural light to fill the interior. A majestic tree adds a touch of elegance to the scene.

4.96 out of 5 average rating, 272 reviews

Grandma's Place an Easy Walk to Woodstock

Simply decorated and conveniently located, Grandma's Place is on a quiet road just minutes from all Woodstock has to offer. Vintage furnishings make this popular rental a fun place to stay. The house shares a roof with Grandma's Apartment but the spaces are separated with a secure and sound proofed door. The only shared areas include the driveway and garden. If you wish to rent only one bedroom, please see link at Grandma's Place - Queen Only and send an inquiry about your desired dates.

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4.97 out of 5 average rating, 171 reviews

Fall Escape | EV | Hot Tub

The Maverick — A Mid-Century Escape Escape to The Maverick, a beautifully restored 1964 Mid-Century Modern retreat just 5 minutes from downtown Woodstock. Featured in Atomic Ranch and Country Home, this secluded design-forward hideaway blends iconic furnishings, soaring skylights, nature, and indoor-outdoor living. Relax on the expansive decks, explore nearby trails, or unwind in the new 7-person luxury spa hot tub beneath the stars. Come for the design, stay for the experience.

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A bright and airy living room features large windows allowing natural light to fill the space. A stylish sectional sofa in warm tones is arranged on a patterned area rug, complemented by a coffee table. Skylights enhance the openness, while artwork decorates the walls.

4.92 out of 5 average rating, 206 reviews

Fabulous Family House nr Woodstock Center

Our gorgeous newly decorated Woodstock abode is the perfect destination for a family vacation. Ideally located in town, walking distance to Woodstock center and the legendary Levon Helms Studios. 15 mins to HITS. Close to hiking, swimming & biking. A fully equipped kitchen, new Weber grill, wood-burning fireplace + plenty of wood & space for everyone. Bring to the end a perfect day upstate day by grilling or playing one of our multiple games inc corn hole, darts, scrabble etc.

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A peaceful outdoor space is presented, featuring a fire pit surrounded by seating chairs on a grassy area. A hammock is seen in the background, providing a cozy spot for relaxation amid lush greenery. The natural setting invites calmness and outdoor enjoyment.

4.91 out of 5 average rating, 535 reviews

Brookside, Walk to Town Center, Dog Friendly

Perfect Catskills basecamp! Three-bedroom getaway an 8-minute stroll to Woodstock’s shop and restaurants yet tucked beside a babbling brook. Why guests love it: • Bright living room with huge couch for cozy fireplace moments with friends and family • Ultra-fast Wi-Fi for work or play (3 desks) • Dog-friendly & fully stocked kitchen • Fire pit • Connected to nature As Superhosts we are committed to keeping the home spotless. Just press the reserve button and relax :)

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4.98 out of 5 average rating, 147 reviews

Spacious, Private, Close to Town, Work From Home

Spacious, modern ranch-style house on 1.9 acres, atop a hill, with plenty of natural sunlight. Designed and decorated for a relaxing time in Woodstock, the home has an open and flowing layout. Conveniently located minutes from the center of town, it's perfect for those who want convenience to shopping and restaurants. A perfect home for a family getaway, work-from-home alternative or company retreat in the Catskills / Hudson Valley. Outdoor fire pit in the front yard!

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Popular amenities for Woodstock house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene outdoor space features a saltwater pool surrounded by lush greenery and fencing. Lounge chairs with brightly colored towels are positioned on the stone patio, inviting relaxation alongside the tranquil water.

4.93 out of 5 average rating, 124 reviews

Summer Paradise - Pool, Fire-pit, Nursery!

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A panoramic view of distant mountains stretches under a clear blue sky. The landscape features a mix of trees and open areas, showcasing the natural beauty of the surroundings.

4.88 out of 5 average rating, 153 reviews

Gorgeous Villa Mntn Views • POOL • hot tub •grill!

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A refreshing swimming pool is surrounded by a wooden deck adorned with colorful flower pots. Comfortable lounge chairs offer a place to relax under a blue umbrella while a table invites outdoor dining. Lush greenery envelops the area, providing a private and serene setting.

4.9 out of 5 average rating, 212 reviews

HOT TUB on Secluded 7acres, Heated Pool, Stream !

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4.97 out of 5 average rating, 129 reviews

Woodstock Family Home w/ Tree House + Heated Pool

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An aerial view captures the red dairy barn, featuring a colorful roof with decorative elements. Surrounding greenery and open fields create a serene backdrop, while a winding path leads to the barn entrance, inviting exploration of the surrounding landscape.

4.99 out of 5 average rating, 277 reviews

The Woodstock Barn House - Sauna, Gym, Jacuzzi

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An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.

5.0 out of 5 average rating, 172 reviews

Upstate Modern Scandinavian Barn in the Catskills

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A spacious living area features a hand-built stone fireplace adorned with decorative elements. Large windows allow natural light to fill the room, which includes a dining space with a long table set for guests. Comfortable seating is positioned around the fireplace on a well-defined area rug.

4.96 out of 5 average rating, 113 reviews

MODERN FARMHOUSE in the WOODS

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4.98 out of 5 average rating, 161 reviews

A wooden exterior is complemented by solar panels on the roof, showcasing sustainability. Surrounding foliage displays autumn colors, with trees and shrubs framing the entrance. The home features a welcoming porch area leading to large glass doors that invite guests inside.

Home in Mount Tremper

Secluded Woodstock Retreat -Heated Pool and Sauna

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Weekly house rentals

A bright sunroom features a comfortable seating area adorned with patterned cushions. Large windows allow natural light to fill the space, complemented by a small lamp and a decorative rug with a floral design. A propane stove adds warmth, while potted plants bring a touch of nature inside.

4.89 out of 5 average rating, 202 reviews

Architect's Farmhouse in Woodstock

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A spacious living area features a charcoal sofa paired with a sleek black armchair. Natural light streams through large windows, illuminating an art piece above a wooden coffee table. A wood-burning stove adds warmth, complemented by a stack of logs nearby.

4.93 out of 5 average rating, 225 reviews

Escape to Pine Lane

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A spacious living room features a large gray sectional sofa paired with a coffee table made of rich wood. Natural light fills the space through multiple windows, highlighting the minimalist decor and a cozy fireplace set against a dark stone wall.

4.99 out of 5 average rating, 154 reviews

Hudson Valley Evergreen Treehouse

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4.95 out of 5 average rating, 370 reviews

A charming farmhouse exterior is presented, featuring a well-maintained porch with seating. The facade showcases a combination of horizontal and vertical siding, complemented by a sloped roof. Lush greenery surrounds the property, enhancing the serene atmosphere of the rural setting.

Home in Kingston

Hudson Valley Hygge House~ comfort in the country!

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A spacious living room features a light-colored sectional sofa and a unique wooden coffee table. A stone fireplace is set against a wood-paneled wall, while large windows provide natural light. The open-concept layout connects to a dining area visible in the background.

4.98 out of 5 average rating, 188 reviews

The Woodstock Getaway

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4.91 out of 5 average rating, 194 reviews

In-Town Woodstock Retreat • Hot Tub • Dog-Friendly

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4.99 out of 5 average rating, 131 reviews

Woodstock Catskills Retreat~Sweet, Private & Views

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4.91 out of 5 average rating, 258 reviews

A spacious two-story home is surrounded by lush greenery, featuring a combination of dark wood and orange exterior accents. A gray car is parked under a covered area, and two blue adirondack chairs sit on the lawn amidst colorful flower beds.

Home in Hurley

Comfortable Woodstock Getaway

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Private house rentals

4.9 out of 5 average rating, 105 reviews

Catskills Retro Retreat- Upstate Home w/ Hot Tub

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A serene landscape is captured, featuring a tall tree with budding leaves beside a rustic barn. Mist gently envelops the grassy area, creating a tranquil atmosphere as light filters through the trees in the background.

4.98 out of 5 average rating, 195 reviews

The Stone House

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4.93 out of 5 average rating, 281 reviews

Home in Hurley

Hot tub with stunning views, 5 min to Woodstock

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A modern living room features a wooden media console with a flat-screen TV and a stylish lamp, against a deep blue accent wall. A framed artwork sits on the console, while a hallway leads to other rooms, showcasing hardwood flooring and a hint of the staircase.

4.86 out of 5 average rating, 266 reviews

Cozy Woodstock Escape · Hot Tub & Village Access

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A bright dining area features a long white table surrounded by wooden chairs. Large glass doors open to a deck with river views. Sunlight fills the space, highlighting the clean lines of the cabinetry and décor in soft, neutral tones.

4.94 out of 5 average rating, 199 reviews

Upstate Waterfront Saugerties Retreat-Near HITS

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Superhost

A serene view of expansive mountains is captured under a clear blue sky, complemented by lush greenery in the foreground. A variety of trees and a rural landscape with a distant red barn can be seen, creating a peaceful natural setting.

4.9 out of 5 average rating, 531 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

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A spacious outdoor dining area features a long wooden table set with plates, wine glasses, and food, surrounded by nature. In the background, a wooden cottage is visible, framed by trees. A cozy fire pit with Adirondack chairs adds to the inviting atmosphere.

4.9 out of 5 average rating, 482 reviews

Hot Tub, Fire Pit, Fully-Fenced Yard, Pellet Stove

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