House holiday rentals in Town of Shandaken

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.

Value · Location · Comfort

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.

Value · Family · Cleanliness

Embrace nature in style @ #killercatmountainhouse

Natural splendor meets seductive style at #killercatmountainhouse, a design-focused retreat 5 minutes from Hunter Mountain—and 13 minutes to Windham Mountain—that delivers a fresh & unexpected Catskills experience. Embrace summer from our expansive deck, hot-barrel sauna, fire pit & roomy hot tub, or unwind by the fireplace w/records & games. Our Parisian-chic décor provides Insta-worthy moments inside & out, while our epic views & amenities allow outdoor enthusiasts to indulge all season long.

Value · Family · Barbecue

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

Family · Value · Wi-Fi

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.

Family · Value · Quiet

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.

Location · Family · Getting around

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.

Value · Location · Long stay

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

Value · Family · Checkout

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!

Location · Value · Amenities

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.

Location · Value · Hiking

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.

Family · Location · Check-in

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!

Family · Location · Indoor spaces