
Holiday rentals with a pool in Shandaken
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Shandaken
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Shandaken rentals with a pool
House rentals with a pool

Private Hudson Valley Country Retreat

Woodstock Family Home w/ Tree House + Heated Pool

Hudson Valley Black Barn w/ Firepit + Fireplace

Canopy Hill House - Modern w/ Pool+Hot Tub+Mt View

4Br Mountain Brook House on 130 acres w/ trails

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

Modern Barn on 12 acres w Sauna, FirePit+swimming

BoHo Scandi Farm Retreat, Fireplace, Dogs Welcome
Apartment rentals with a pool

Cozy Gem with Mountain Views

Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub

Windham Condo

Hideaway Windham/Hunter Fireplace, Snow & Skiing

4 Bedroom Condo, Close to Golf Courses and Biking

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

Luxury Ski in Ski out Condo + Amenities

Autumn Retreat w/wood burning fireplace
Other holiday rentals with a pool

Serenity Meadows: Heated pool and hot tub, Firepit

Luxe Family Retreat w/ FP, HT & Cabana

The Happy Hemlock

Mansion of Belleayre Mountain! + POOL/SAUNA

Cold Brook Cottage

The Bend: Stony Clove Suite • Pool • Sauna • Creek

The Kripplebush Farmhouse: Pool, WBF, Location!

Fawn Hill Cabin: Cozy Log Cabin in Phoenicia
Quick stats about holiday rentals with a pool in Shandaken
Total rentals
80 properties
Nightly prices starting at
€ 69 before taxes and fees
Total number of reviews
2.7K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Destinations to explore
- Plainview Holiday rentals
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- Philadelphia Holiday rentals
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- Rentals with a sauna Shandaken
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- Fitness-friendly rentals Shandaken
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- Rentals with pools Ulster County
- Rentals with pools New York
- Rentals with pools United States
- Hunter Mountain
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- John Boyd Thacher State Park
- Howe Caverns
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Bash Bish Falls State Park
- Zoom Flume
- Brotherhood, America's Oldest Winery
- Hudson Highlands State Park
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Windham Mountain
- Taconic State Park
- Villa Roma Ski Resort
- Plattekill Mountain
- Opus 40
- Hunter Mountain Resort
- Benmarl Winery
- Millbrook Vineyards & Winery
- Hudson Chatham Winery