Holiday rentals with a pool in Shandaken

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Top-rated rentals with a pool in Shandaken

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
A bright and modern kitchen features white cabinetry and a stylish backsplash. An island with four wooden stools provides seating. Appliances include a refrigerator, dishwasher, and coffee maker, while natural light fills the space from overhead lighting and large windows.
Townhouse in Hunter
4.85 out of 5 average rating, 185 reviews

Gorgeous Mountain View | Ski/Fast Wi-Fi/Wood Stove

Welcome to your amazing Catskills retreat in Hunter, NY! Marvel at the prime location with spectacular views situated only a 5 minute drive to Hunter Ski Mountain. Near hiking trails, waterfalls, antique shops and excellent restaurants. * 2 mins to Hunter North * 5 mins to Hunter base lodge * 13 mins to Windham * 15 mins to Colgate lake While at home enjoy views of the mountain on our deck - bask in the sun or grill a rack of ribs during the day or enjoy a glass of wine and stargaze at night.

Top guest favourite
A cozy living space is highlighted by a light wooden floor and a white shiplap ceiling. A comfortable brown leather couch and an orange accent chair provide seating. A wooden coffee table sits in front of the sofa. Wall art and a floor lamp add warmth to the room.
Cottage in Kingston
4.93 out of 5 average rating, 394 reviews

Kapitan’s Cottage Private Upstate Catskill Retreat

A vintage rustic country retreat with two floors with modern amenities. 2BR, full & half bathroom. Family & Pet friendly. Large yard surrounded by a mature tree line for secluded privacy. Private stone deck w/ fire pit, BBQ & comfortable deck furniture. Summer Pool access and Generator on site. Close to Kingston, High Falls, Stone Ridge and Woodstock yet just far enough out to feel you're away from city hustle and bustle. Close to miles of hiking, outdoor activities, parks & Ski slopes.

Top guest favourite
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.
Home in Saugerties
5 out of 5 average rating, 158 reviews

Upstate Modern Scandinavian Barn in the Catskills

Renovated 1850's barn with 3 bedrooms and an ample loft space that can serve as a fourth. The house also has a large rec room with cathedral ceiling buttressed by hand-hewn beams, well-equipped kitchen, Scandinavian wood stove, sauna, home gym, and projector. Outside: 2 private decks with amazing views of Overlook Mountain, private grill, private hot tub. On property: shared tennis court, swing set, fishing pond, heated pool (summer only). 2 hours from NYC, 10 min. to Woodstock & Saugerties.

Guest favourite
An aerial view showcases a modern dome structure on a spacious property, illuminated against the night. Surrounding pathways are lined with lights, enhancing the serene outdoor setting. Nearby, a tent with soft lighting hints at an inviting gathering space.
Dome in Hobart
4.92 out of 5 average rating, 193 reviews

Mtn View Lux Dome w/ Heated Plunge Pool

This luxury dome is a modern home perched on a mountain top. Our aim is to combine the comforts of a large hotel suite with all the healing qualities of nature. Venture out or hike our own trails leading to a pond and a stream in the woods. Suited for long term WFH stays! We have Fiberoptic internet (ethernet avail) and plenty of space for your setup. Stroll the property at lunch or jump in the heated plunge pool between calls. Ask me about a special offer for long term stays. (14 days +)

Top guest favourite
Apartment in Windham
4.9 out of 5 average rating, 220 reviews

Hideaway Windham/Hunter Fireplace, Snow & Skiing

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Guest favourite
An aerial view captures a charming cabin surrounded by lush trees, with a vibrant sunset sky in shades of pink and purple. The spacious yard is highlighted by a hot tub, outdoor seating area, and fire pit, inviting relaxation and gatherings in nature.
Cabin in Livingston Manor
4.97 out of 5 average rating, 327 reviews

Experience The Zen House

Enjoy your own private indoor movie theater with 7.1 Klipsch Premiere Surround Sound and leather recliner seats, a spa with a cold plunge pool & sauna, and a hot tub to reach the maximum level of relaxation. Play a game of ping pong, enjoy the fireplace outside and inside along with 5 acres! Amenities Include: - Hot Tub - Bath House with Sauna & Cold Plunge Pool - 12 Person Theater with immersive visual & surround sound + recliners - Game Room - Outdoor Fire Pit - Hammock & much more!

Top guest favourite
Cabin in Shandaken
4.96 out of 5 average rating, 217 reviews

Catskills Retreat: 4Br l Fire-pit l Hot Tub l Hike

7 min drive to Phoenicia 10 min drive to Belleayre 25 min drive to Hunter 35 min drive to Windham Renovated 1920’s cabin style home nestled on 4 acres in the Catskill Mountains. Easy to get to and conveniently located near great restaurants, skiing, hiking, tubing, fishing, and swimming holes. A ton of outdoor space to enjoy in addition to our fully private seasonal pool (Late May-Sept). 6 person hot tub is available year round. Not for parties!! Please be mindful of our neighbors!

Top guest favourite
A wooden lounge chair is positioned near a serene saltwater pool, surrounded by lush greenery. The pool's clear water reflects the inviting outdoor space, which is complemented by concrete paving and a manicured lawn.
Home in Cottekill
4.95 out of 5 average rating, 288 reviews

Peace & Privacy - High Falls (hot tub & salt pool)

Enjoy the serenity of this contemporary home on six private acres central to all the Hudson Valley has to offer; just 20 min. from the NYS Thruway. Year-round hot tub, seasonal salt water pool, fireplace, gourmet kitchen, and large deck & patio w/ fire pit make this the ultimate getaway. Sports enthusiasts, shoppers, and diners will delight in how close we are to amazing Catskills attractions. New Paltz, Kingston, Mohonk Preserve and Minnewaska State Park are just 15 minutes away.

Superhost
Cabin in South Kortright
4.89 out of 5 average rating, 265 reviews

Contemporary Cabin w/ Hot Tub, Lake & Fireplace

Ticking all the boxes, this beautiful cabin has everything you could want for your retreat from city life! Five acres of private forest encapsulates the perfect seasonal mood as you step from the great room onto the huge wrap-around deck. Relax and enjoy the property with its hot tub, fireplace, A/C, BBQ grill and poolside loungers. For the adventurous at heart, check out the community shared lake access (non fishing), rivers, hiking trails and ski stations right at your fingertips.

Guest favourite
A wooden deck is furnished with comfortable seating and a coffee table, providing a serene view of rolling mountains and a tranquil pond. The sky is filled with fluffy clouds, reflecting warm hues as the sun sets, enhancing the natural beauty of the landscape.
Cottage in Denver
4.94 out of 5 average rating, 153 reviews

Country Cottage w/ HOT TUB & Views

Welcome to the most peaceful and tranquil place in the world. Our beautiful home is situated on 3 acres of private land with a private pond and incredible views of the mountains. Escape your life and stressors, and come stay in the fresh air where all you will hear are birds chirping - no sirens, cars or people. The cottage is fully stocked to be enjoyed for all 4 seasons! Relax in the hot tub, or go for a swim in the pond. Our property is the perfect vacation getaway.

Top guest favourite
An aerial view showcases a secluded log home surrounded by lush green trees on a mountainside. The property features a pool and well-maintained landscaping, creating a serene natural environment. Rolling hills and forest are visible in the background, enhancing the sense of privacy and tranquility.
Chalet in Olivebridge
4.99 out of 5 average rating, 170 reviews

Spruced Moose Lodge & Treehouse w/ New Hot Tub!

Secluded log home nestled in 5 acres of Catskill mountain forest, with 4 bedrooms & 3.5 baths (incl. basement with built-in full size bunks). Enjoy a sunroom, screened porch, pool+ brand new hot tub, projection screen home theater & a treehouse that resembles a floating pirate ship 30 feet up in the trees. We renovated the kitchen & master bed with new walls of windows in May - pics to come! Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Guest favourite
Cabin in Lanesville
4.94 out of 5 average rating, 357 reviews

Only Ski In Out on Mtn | Hike, Golf, Fish, Relax

Mountainside 1 bedroom cabin that fits 4! Ski on/off Hunter Mountain right from your doorstep. Enjoy hiking within a 5-minute drive or walk right onto the mountain from your porch. Unbeatable location on Hunter Mountain, short drive to the picturesque, colorful village of Tannersville, majestic Kaaterskill Falls, and renowned fishing! Fully stocked kitchen/bathroom, full entertainment system with streaming, high-speed WiFi, and dedicated work space.

Popular amenities for Shandaken rentals with a pool

When is the best time to visit Shandaken?

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Avg. price$237 SGD$233 SGD$213 SGD$206 SGD$206 SGD$247 SGD$293 SGD$288 SGD$223 SGD$195 SGD$245 SGD$208 SGD
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Quick stats about holiday rentals with a pool in Shandaken

  • Total holiday rentals

    Explore 80 holiday rentals in Shandaken

  • Nightly prices starting at

    Shandaken holiday rentals start at $104 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,710 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    70 of Shandaken holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Shandaken rentals

  • 4.7 Average rating

    Shandaken stays receive an average rating of 4.7 out of 5 from guests

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