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House holiday rentals in Town of Shandaken

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Top-rated house rentals in Town of Shandaken

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Guest favourite
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.
Home in Woodstock

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.

4.94 out of 5 average rating, 398 reviews
Top Guest favourite
Home in Phoenicia

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.

4.99 out of 5 average rating, 134 reviews
Top Guest favourite
A cozy living area features a stone fireplace as its focal point, with a wood-burning stove and a mid-century cabinet. Colorful textiles cover the floor, and a mix of seating options, including a green chair and a couch, invite relaxation. Light streams through the two windows.
Home in Phoenicia

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

Welcome! Stony Clove Cottage sleeps a maximum of 4 adults and 2 children. There are 2 queen beds and a bunk bed 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

4.98 out of 5 average rating, 355 reviews
Top Guest favourite
Two Adirondack chairs are positioned near a tranquil lake, offering views of the surrounding green trees and hills. A fire pit is located in front of the chairs, with large rocks scattered around the area, enhancing the natural setting.
Home in Chichester

Stunning Pvte Lakehouse•Swim•Hike•Mntn Views•F/pit

Wake up to stunning mountain views & enjoy a coffee next to your own private lake surrounded by 5 secluded acres of the bucolic Catskill Mountains. Swim in the clean, clear lake; lie out on the swim dock; row across the lake in the row boat; grill on the wrap-around porch; cook for friends in the gourmet kitchen, or simply relax by the fire (wood-burning fireplace + lakeside FIREPIT). Mins to breweries, hiking & the trendy town of Phoenicia. You need never leave! This is the ULTIMATE getaway.

4.97 out of 5 average rating, 187 reviews
Guest favourite
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

Mt. Wonder: Big Cozy Cabin with Wow View

Welcome to Mt Wonder. With a wood burning hot tub, this quiet cabin perches on 18 acres with creek access, a vast forest & the greatest view in the county. 10 min to Woodstock. Seeking a vacation w friends or a romantic sojourn? Enjoy this rustic 2br 1ba cabin, cozy & spacious - a unique magical feel. Mega amenities incl the tub, wood stove & stocked kitchen. Peruse our books, vibe w the view, enjoy hikes & cute towns. Need more space? Try my cousin's cabin called "Wonders Never Cease"

4.93 out of 5 average rating, 276 reviews
Guest favourite
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 Town of Shandaken

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 #2026-STR-AO-105.

4.95 out of 5 average rating, 223 reviews
Guest favourite
A cozy wooden house is featured, surrounded by lush green grass. A cedar sauna is positioned nearby, illuminated softly, while the house displays inviting outdoor lights. Steps lead to the front entrance, framed by a natural stone path and surrounding foliage.
Home in Phoenicia

Catskills Log Home With Fireplace & Outdoor Sauna

Enjoy the perfect Catskills getaway in our beautiful log house, featuring a wood-burning fireplace, outdoor sauna, 3 BRs, 2 full bathrooms, large, covered balcony with mountain views, TV & game room on the lower level, with a billiard/ping-pong table and fold-out couch, fire pit, grill, hammock, private yard & fast wifi! Book a memorable Catskills trip for couples, families, or friends. Unwind indoors, dine out, or enjoy the great outdoors with lots of nearby hiking and skiing options.

4.9 out of 5 average rating, 231 reviews
Top Guest favourite
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

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

Spacious, peaceful lux cabin atop the Catskills. Enjoy mountain views and soak in the hot tub. Catch up in the vaulted room by the stone fireplace w/ a wide game selection, with a 2nd living room downstairs. Host a dinner party with our fully equipped kitchen. 20 mins to 6 towns. Visit breweries, antique shops, dine, hike, fish, golf, or relax. Great for groups, families, kids & pets. Fast 600mb internet, AC, EV charger, generator. WFH, newborn, pet friendly. 3+ nights get discounted rate

4.99 out of 5 average rating, 169 reviews
Guest favourite
A modern cabin design features broad wooden slats and floor-to-ceiling glass doors. A spacious deck includes loungers and a hot tub, surrounded by lush greenery, enhancing the outdoor aesthetic. Soft lighting illuminates the seating area, creating a welcoming environment.
Home in Hunter

Modern House with Mountain View @Getawind

Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

4.96 out of 5 average rating, 230 reviews
Top Guest favourite
Home in East Jewett

Creekside Couple's Retreat w/Hot tub, Sauna & More

Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

4.99 out of 5 average rating, 151 reviews
Top Guest favourite
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

10 Min from Bellayre! Gingerbread House!

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.

4.98 out of 5 average rating, 169 reviews
Top Guest favourite
The exterior view showcases the two-story Flatrock House, featuring a combination of wood and stone siding. A welcoming entryway is complemented by a stone pathway lined with greenery, while surrounding trees and a lush yard enhance the natural setting.
Home in Town of Shandaken

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!

5.0 out of 5 average rating, 144 reviews

Popular amenities for Town of Shandaken house rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favourite
An aerial view showcases a charming farmhouse surrounded by lush greenery and the Catskill Mountains. A rectangular in-ground pool is visible in the backyard, bordered by a grassy area. A quiet country road runs alongside the property, contributing to the tranquil setting.
Home in Grahamsville

Spacious Catskills Farmhouse on over 5 acres!

4.91 out of 5 average rating, 125 reviews
Guest favourite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

4.88 out of 5 average rating, 220 reviews
Guest favourite
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

4.98 out of 5 average rating, 161 reviews
Guest favourite
A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.
Home in Kerhonkson

A Very Cozy House With a Very Big Yard

4.95 out of 5 average rating, 409 reviews
Guest favourite
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.
Home in Saugerties

Summer Paradise - Pool, Fire-pit, Nursery!

4.93 out of 5 average rating, 124 reviews
Superhost
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
Home in Newburgh

Entire Home, Private Indoor Pool

4.81 out of 5 average rating, 136 reviews
Top Guest favourite
Home in Kerhonkson

Luxe modern A Frame, Hot tub and new heated pool

4.97 out of 5 average rating, 117 reviews
Top Guest favourite
Home in Athens

Lake House close to Skiing & Indoor Hot Tub

4.96 out of 5 average rating, 112 reviews

Weekly house rentals

Top Guest favourite
A circular stone fire pit area is surrounded by five red Adirondack chairs on a well-maintained grassy lawn. Lush green trees provide shade, with a view of a charming house in the background, contributing to a serene outdoor setting.
Home in Big Indian

Birch Creek Mountain House

4.95 out of 5 average rating, 139 reviews
Top Guest favourite
Home in Halcottsville

Luxury farmhouse at the porch

5.0 out of 5 average rating, 120 reviews
Top Guest favourite
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!

4.95 out of 5 average rating, 370 reviews
Guest favourite
An open living space features a stone fireplace at its center, flanked by large windows that provide natural light. Comfortable seating is arranged around a coffee table, and a dining area with chairs is visible in the background, all designed with rustic cedar beams overhead.
Home in Big Indian

Contemporary MOUNTAINSIDE home

4.97 out of 5 average rating, 195 reviews
Guest favourite
A charming farmhouse is set alongside a serene pond, with lush greenery and mountains in the background. A balcony extends from the upper level, and a small dock is visible on the water. Adjacent structures contribute to the rural appeal.
Home in Arkville

Scenic farmhouse near Belleayre Mountain

4.83 out of 5 average rating, 153 reviews
Top Guest favourite
A spacious outdoor deck is showcased, featuring two white lounge chairs positioned opposite a small glass table. Lush green hills are visible in the background under a partly cloudy sky, highlighting the serene natural surroundings of the retreat.
Home in Halcottsville

Spacecraft Sanctuary x Stargate Self-Care Retreat

4.93 out of 5 average rating, 390 reviews
Top Guest favourite
A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.
Home in Accord

Accord River House

4.99 out of 5 average rating, 106 reviews
Guest favourite
A spacious country house is surrounded by lush greenery and mature trees. A gazebo is elegantly positioned on the lawn, while a meandering stream flows gently nearby, enhancing the natural setting.
Home in Pine Hill

Birch Creek Retreat ~ 8BR/8BA New Hot Tub + Sauna

4.96 out of 5 average rating, 160 reviews

Private house rentals

Top Guest favourite
Home in Woodstock

Woodstock Catskills Retreat~Sweet, Private & Views

4.99 out of 5 average rating, 131 reviews
Top Guest favourite
A spacious living room features high wooden ceilings and warm-toned walls. A cozy seating arrangement includes a leather sofa and armchair, placed around a central area rug. A fireplace is surrounded by decorative elements and neatly stacked firewood. Large windows provide natural light and views of the outdoors.
Home in West Kill

Waterfront Lodge near Breweries • Group Home

4.97 out of 5 average rating, 150 reviews
Top Guest favourite
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.
Home in Saugerties

The Stone House

4.98 out of 5 average rating, 195 reviews
Top Guest favourite
A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.
Home in Staatsburg

Boulder Tree House

4.99 out of 5 average rating, 138 reviews
Top Guest favourite
The exterior of the cottage features a light-colored facade with a prominent wooden front door. A stone walkway leads through a well-maintained lawn to the entrance, complemented by a porch and large windows reflecting the natural surroundings.
Home in Andes

Andes Cottage

4.99 out of 5 average rating, 114 reviews
Top Guest favourite
A large hot tub is positioned beneath a wooden shelter, surrounded by lush greenery. Adirondack chairs are placed nearby, providing a comfortable seating area. The bubbling water of the hot tub invites relaxation, set against a backdrop of tall trees and vibrant foliage.
Home in Arkville

Mountain Escape with a Large Hot Tub and more!

4.96 out of 5 average rating, 112 reviews
Top Guest favourite
A spacious living area is defined by large windows, allowing natural light to fill the room. A central wood stove offers warmth, while a sectional couch invites relaxation. Decorative bookshelves and comfortable poufs enhance the inviting atmosphere, complementing the serene surroundings.
Home in Prattsville

Tranquil, Modern Retreat w/ Great Views, Sauna

4.96 out of 5 average rating, 112 reviews
Guest favourite
An outdoor hot tub is situated on a wooden deck, with a 55-inch TV mounted on the wall nearby. Soft lighting creates an inviting ambiance as the sun sets behind distant hills, offering a serene escape for relaxation and entertainment.
Home in Lanesville

Hunter Mtn Ski Chalet! Hot Tub, Outdoor TV Firepit

4.91 out of 5 average rating, 185 reviews

Destinations to explore