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House vacation rentals in Shandaken

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Top-rated house rentals in Shandaken

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Top guest favorite

Home in Roxbury

5 out of 5 average rating, 167 reviews

Private 3BR escape w/ sweeping Mt Views & Firepit!

Click: "Show more" to read description before booking. NO PETS Perched high on a private road, The Ridge is a 3 BR / 2 bath newly constructed modern farmhouse w/ sweeping mountain views. Relax & dine outdoors on the wrap around deck & discover all of the comforts of home inside the open concept living space. Set on 5 mountainside acres, 3 min to Roxbury town & 10 min to wedding venues. Outdoor adventures await- 4 season activities at ski mountains, hiking, golf, farmers markets & culinary tours

Top guest favorite

Home in Phoenicia

4.99 out of 5 average rating, 102 reviews

Modern dreamy Hudson Valley home

Gorgeously renovated 3-bedroom home in the heart of the Catskills. Enjoy your own private firepit and outdoor dining, cook and recharge in the light-filled kitchen, feel pampered in the spa-like bathroom with a heated floor - all within 5 minutes of the Phoenicia Diner & Railway Explorers. Nestled in the mountains, this home is the perfect for unwinding & offers green amenities including an EV charger and new eco heating and cooling system. Large windows bring light & views to this dreamy home.

Top guest favorite

A peaceful landscape is captured, featuring rolling hills under a clear blue sky. Lush green fields transition into vibrant fall foliage, showcasing various trees. Subtle sunlight casts gentle shadows across the scene, enhancing the serene ambiance of the natural surroundings.

Home in Woodstock

4.99 out of 5 average rating, 110 reviews

Woodstock Catskill Escape: Bright Views & Private

❤️A beauty in scenic nature with scenic rides to charming historic towns, Woodstock, Kingston, and Phoenicia, Saugerties, ski resorts and many outdoor adventures & various dining options nearby. 🥾 😊 PinkyHouse, where friends and family gather for a lovely time and fond memories, welcomes you to its bright, sweet, peaceful, and private setting on 3.5 acres of green & forest with a brook and view of mountains. Enjoy your relaxing getaway here! 😊 🥾🚙⛰️ * No Pets & No-smoking xoxox anne 😊

A rustic cabin sits amid vibrant autumn foliage, surrounded by tall trees. A wooden deck wraps around the cabin, providing a spacious area for relaxation. A gravel path leads to the cabin, with a single chair positioned on the lush green lawn, inviting guests to enjoy the serene environment.

Home in Mount Tremper

4.93 out of 5 average rating, 232 reviews

Mt. Wonder: Cold Plunge, Sauna, Hot Tub and View

Welcome to the most splendid view in the Catskills. With a private outdoor spa. And just 10 min to Woodstock. This secluded cabin sits on 18 acres w/ private creek access & forest. Seeking a vacation w friends or a romantic escape? This is the place. Enjoy this rustic 2BD 1ba cabin year-round, incl the natural hot tub, sauna & cold plunge Amenities galore incl the spa, BBQ, firepit, games, wood stove & stocked kitchen. Peruse our books, be in nature or enjoy hikes & towns. This is the one.

The exterior of a charming blue house features large windows surrounded by lush greenery. A small guest cottage is visible nearby, set in a well-maintained yard with a grassy area and trees. A distinctive sculpture rests on a rock in the foreground.

Home in Shandaken

4.96 out of 5 average rating, 201 reviews

Catskills Mountain House with a Separate Cottage on a Creek

Beautifully furnished & charming with plenty of outdoor space to play around, have a fire, grill- and beautiful barn. A small stream runs on the edge of the property, perfect to sit beside, and a guest cottage with extra sleeping space (queen, trundle and aerobeds/ bathroom). It's full of unique, hand-crafted and antique furnishing and decor, (fun-fact, former residence of Freakonomics author Stephen Dubner). You'll have free range of the whole place! Shandaken STR Licence #2024-STR-AO-105.

A cozy outdoor seating area is surrounded by trees and fallen leaves. Four red chairs are positioned around a wooden table, with a fire pit in the center. String lights are draped overhead, creating a warm ambiance in the natural setting.

Home in Livingston Manor

4.93 out of 5 average rating, 144 reviews

Parkston Schoolhouse

Relax and unwind in this historic converted one-room schoolhouse. Built in 1870, the Parkston Schoolhouse served all grade levels in the Livingston Manor area. The schoolhouse was retired and converted to a cozy cottage style home in the mid 20th century and has recently been renovated into a stylish tiny home getaway. The home is tucked into the hillside along the beautiful, winding Willowemoc Creek and is set amidst a lush Catskill landscape just a five minute drive from Livingston Manor.

A serene view of a flowing river bordered by smooth rocks and a grassy shoreline. Lush trees line the riverbank, with distant mountains visible under a soft, golden sunset. The tranquil scene invites leisurely walks along the water's edge.

Home in Mount Tremper

4.91 out of 5 average rating, 200 reviews

Rippleside Retreat - Stay and Relax

LOCATION, LOCATION! Spacious and quiet creek-front and mountain view home. Near Phoenicia and Woodstock for shopping, browsing art galleries, and fine dining. Plenty of hiking trails, fishing, and tubing in the warmer months, and close to skiing at Belleayre, Hunter, Windham, and Plattekill Mountains for winter enthusiasts. The home is conveniently located near the Emerson Resort and Spa, Foxfire Mountain House, Howland House, Mount Tremper Arts, and Onteora Mountain House wedding venues.

Top guest favorite

A bright living area features a blue couch adorned with decorative pillows. A wooden coffee table sits in front, complemented by a woven bowl. Vibrant artwork is displayed on the walls, and a stained glass door invites natural light. A staircase leads to the upper level.

Home in Phoenicia

4.98 out of 5 average rating, 308 reviews

Stony Clove Cottage - sleeps 6, *maximum 4 adults*

Welcome! Stony Clove Cottage sleeps a maximum 4 adults and 2 children. There are 2 queen beds and a bunkbed for children only. Located in the beautiful Catskill Mountains just 2 hours 15 mins. from NYC. Two great ski mountains, Hunter and Belleayre, are each 15 minutes away. Close to amazing hiking trails. Listen to the sound of the Stony Clove Creek and enjoy being in nature, while just 1 mile from Phoenicia's Main Street. Beautiful in all seasons! Shandaken STR License # 2023-STR-AO-059

The exterior of the house is viewed from the backyard, showcasing a spacious deck with a red umbrella. Lush green grass surrounds the area, with tall trees providing shade. The backdrop features rolling hills, creating a serene outdoor environment.

Home in Big Indian

4.91 out of 5 average rating, 133 reviews

5 minutes to Belleayre! The Birch Creek BelleHouse

Our modern home is clean and bright. Just minutes from skiing, hiking, swimming, and fine dining - The gorgeous Birch Creek is right outside . Feel free to take a dip. - A quick walk to Pine Hill Lake for swimming, boating and more. - Many spectacular hiking trails nearby. - It's an easy five minute drive to Belleayre Ski Center - Close to the best restaurants in NY State. - Pets are welcome with an additional fee. - Next door to our other property, the Birch Creek Cottage.

A small office nook features a gray sofa adorned with a textured throw pillow. A wooden desk with two chairs is positioned near a window, allowing natural light to brighten the space. A woven mirror and a framed art piece complete the design, enhancing the cozy atmosphere.

Home in Mount Tremper

4.93 out of 5 average rating, 283 reviews

Overlook Creek Cottage 1 Near Phoenicia

Located on the Esopus, Overlook Creek Cottage is a newly renovated space including modern kitchen and bathroom amenities, mid century modern design with a Bohemian flair and proximity to destinations such as the town of Phoenicia, The Pines restaurant, Phoenicia Diner, Foxfire Mountain House, The Emerson Resort and Mt. Tremper Arts. Nearby to hiking trails and other towns such as Woodstock and Kingston as well as the Ashokan Reservoir.

Top guest favorite

A charming Swiss chalet is nestled among tall trees, surrounded by lush greenery. The house features a welcoming deck and multiple windows that provide natural light. A stone path leads to the entrance, inviting guests to explore the tranquil outdoor setting.

Home in Big Indian

4.98 out of 5 average rating, 116 reviews

Gingerbread House- a 1950s Catskills Chalet

Perched high among the trees, Gingerbread is a 1950’s Swiss chalet that sits on 4 acres. This is the house everyone slows down for, points and says ‘ that’s the house I would want Upstate’. Well ….she's taken. But I am so happy to welcome you as guests for a short period of time. Gingerbread comes with all the little touches making it feel like the perfect home away for a week, weekend or however long you can escape your regular life.

Top guest favorite

Home in Shandaken

5 out of 5 average rating, 129 reviews

Swim in the Esopus, Close to Phoenicia and Skiing

Flatrock House is located in the heart of The Catskill Mountains. Originally built in the 1950's, our 3200 square ft house was once a bar, disco & casino. Spend your time relaxing in our one-of-a-kind, curated home on 8.5 acres of forever green forest. Whether you're playing in the creek, exploring the forest, picnicking in the yard or just relaxing in front of the wood-burning-stove, you'll feel like you've truly gotten away!

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Shandaken house rentals

Free parking on premises

Air conditioning

House rentals with a hot tub

An inviting BBQ hut features a central fire and cooking space, surrounded by wooden benches. Two glasses of red wine sit elegantly next to a platter of grilled meats, with a warm orange glow emanating from the flames. The natural wood interior adds a rustic touch.

4.93 out of 5 average rating, 182 reviews

Mountain house w/ Scandinavian BBQ hut Spa & more!

Home in Mount Tremper

4.96 out of 5 average rating, 109 reviews

Chef's kitchen, seclusion, and breathtaking views

Top guest favorite

The exterior of a Mid Century Mod house is showcased at night, illuminated by soft outdoor lights. The building features large windows that reveal glimpses of the interior, while the surrounding lawn is landscaped with grass and scattered fallen leaves.

Home in New Paltz

4.98 out of 5 average rating, 500 reviews

midcentury mod * HOT TUB * walk out trail 2 mohonk

Home in Olivebridge

4.92 out of 5 average rating, 461 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

Top guest favorite

A cozy outdoor space features comfortable seating and a modern fireplace, set against a stunning backdrop of lush trees and a colorful sunset. A hot tub is visible nearby, inviting relaxation. Soft lighting adds a warm touch to the tranquil atmosphere.

Home in Lexington

4.99 out of 5 average rating, 122 reviews

Mountain View Chalet: AC, Hot Tub, Firepit, Games

Top guest favorite

A spacious living area features a comfortable gray sofa alongside a wooden coffee table. Shelves adorned with books and decor create an inviting atmosphere. Floor-to-ceiling windows allow natural light to illuminate the space, while a unique patterned area rug adds texture beneath.

4.95 out of 5 average rating, 204 reviews

Hot tub with stunning views, 5 min to Woodstock

A bright living area features a cozy seating arrangement with light-colored furniture and wooden accents. Shelves display various decorative items, while a large window allows natural light to fill the space. The entrance showcases a beautifully carved door and soft greenery adds a touch of nature.

Home in Woodstock

4.92 out of 5 average rating, 186 reviews

Serene Retreat w/ Cedar Hot Tub & Fire Pit

A spacious living area is highlighted by large windows allowing natural light to fill the space. The hardwood floor complements a dining table with chairs, and a cozy seating arrangement near a fireplace. Decor includes plants and a guitar in the corner.

Home in Parksville

4.97 out of 5 average rating, 184 reviews

Cooley Mountain House *Hot Tub*

House rentals with a pool

An above-ground pool is surrounded by a wooden deck featuring lounge chairs. Lush greenery and trees provide a natural backdrop, while a fenced area with a swing set is visible in the distance, creating a serene outdoor space for relaxation.

Home in Woodstock

4.88 out of 5 average rating, 172 reviews

Shula | Farmhouse | Pool, Fire pit, Hot tub

An aerial view captures the sprawling property, surrounded by lush trees. The heated salt-water pool is visible, framed by a wooden deck and lounge chairs. A spacious outdoor deck with seating and a fire pit enhances the inviting outdoor space.

Home in Woodstock

4.86 out of 5 average rating, 214 reviews

Spacious Woodstock Haven Pool, Fire Pit, Nature

An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.

Home in New Paltz

4.86 out of 5 average rating, 167 reviews

Scenic River View Escape | New Paltz

A private saltwater pool is surrounded by lush greenery, featuring a smooth stone deck. The clear blue water invites relaxation, while steps lead into the pool. Trees provide natural shade along the perimeter, creating a serene outdoor setting.

Home in Woodstock

4.86 out of 5 average rating, 136 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

A charming farmhouse is framed by vibrant autumn foliage, with a wooden gate leading to a gravel path. Leaves strewn across the ground add to the seasonal ambiance, while the white exterior of the house is complemented by dark green accents.

Home in Saugerties

4.94 out of 5 average rating, 154 reviews

5BR close to Village | Diamond Mills | HITS | Pool

Top guest favorite

A spacious deck features two comfortable chairs and a round table at its center, offering a clear view of the expansive Catskill Mountain landscape. Lush greenery and rolling hills stretch into the distance under a bright blue sky.

Home in Stamford

4.98 out of 5 average rating, 120 reviews

Hawk View

An open living space features a grand piano positioned near large windows that offer views of the surrounding mountains. A light-colored sectional sofa and a round coffee table create a comfortable seating area, accented by a dining table beside it. Natural wood beams add architectural interest.

Home in Saugerties

5 out of 5 average rating, 153 reviews

Upstate Modern Scandinavian Barn in the Catskills

A welcoming front patio is shown with two chairs positioned near the house. Surrounding lush green grass extends to the horizon, featuring a backdrop of gentle hills and a few distant buildings, including a red barn, under a clear blue sky.

Home in Narrowsburg

4.95 out of 5 average rating, 210 reviews

Modern House with Private Pool, Hot-Tub, Fireplace

House rentals with free parking

A wooden dock extends over the calm water, featuring two lounge chairs facing the serene lake. Lush greenery borders the lake, with rolling hills visible in the background under a partly cloudy sky.

Home in Swan Lake

4.94 out of 5 average rating, 135 reviews

Bright Lake House with Hot Tub, Kayaks & Firewood

A side view of the house is captured, showcasing a welcoming porch and a gently sloping lawn. Lush greenery surrounds the area, with trees in the background complemented by distant mountains under a clear blue sky.

Home in Margaretville

4.95 out of 5 average rating, 199 reviews

Secluded Catskills Retreat with Mountain Views

Top guest favorite

The exterior of the house is framed by lush greenery, featuring a wooden pathway leading to the entrance. Potted plants with purple flowers adorn the area, and a decorative wind chime hangs in a circular frame, enhancing the natural setting.

Home in Catskill

4.97 out of 5 average rating, 190 reviews

Modern Prefabricated Architectural Retreat

Top guest favorite

A modern house is seen, constructed with a combination of stone and wood materials. Large picture windows are positioned throughout, allowing natural light to flow in. A landscaped rocky path leads to the entrance, surrounded by greenery and trees.

Home in Rhinebeck

5 out of 5 average rating, 224 reviews

Eagle Rock House

Top guest favorite

4.98 out of 5 average rating, 117 reviews

Lux Modern Cabin at Hunter Mountain

A warm living space is highlighted by neutral tones and natural light flowing through large windows. A comfortable sofa is paired with a wooden coffee table, and a TV is mounted on the wall. Green plants are placed thoughtfully around the room.

Home in Big Indian

5 out of 5 average rating, 16 reviews

Green Valley House: four-season Catskills getaway

The cozy living area features a green sectional sofa adorned with patterned cushions. Two orange accent chairs are positioned around a unique coffee table. A vintage wooden side table and a television set against a light wall complete the space, illuminated by warm overhead lighting.

Home in Phoenicia

4.93 out of 5 average rating, 174 reviews

Cozy getaway. Close to all. Heart of Phoenicia

Home in Halcottsville

4.93 out of 5 average rating, 353 reviews

Spacecraft Sanctuary x Stargate Self-Care Retreat

Quick stats about house rentals in Shandaken

Total rentals
160 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
12K reviews
Family-friendly rentals
160 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
20 properties have a pool

Destinations to explore