
Holiday rentals with a pool in Shandaken
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Top-rated rentals with a pool in Shandaken
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Only Ski In Out on Mtn| Hike, Golf, Fish, Recharge
Slopeside 1BR cabin sleeps 4! Step right onto Hunter Mountain from your porch or drive 5 min to scenic hiking trails. Prime location near the charming, colorful village of Tannersville. Enjoy a fully stocked kitchen & bath, high-speed WiFi, and an entertainment system with Netflix & all your other favorite streaming! Stay longer with the convenience of a W/D & dishwasher. Cozy up by the fireplace, take in the mountain views, or explore nearby dining, breweries, and outdoor adventures year-round!

4Br Mountain Brook House on 130 acres w/ trails
Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

Secluded Woodstock Retreat with Pool and Sauna
Stunning, tranquil mountainside retreat with exposed beams, saltwater swimming pool, sauna, fireplace, soaking tubs and rain shower. Situated on a 5-acre wooded hilltop a ten minute drive from Woodstock and close to miles of walking trails. Roast marshmallows on the fire pit, flip burgers on the top of the line charcoal grill, and enjoy one of the best stargazing spots around. Indoors, find a well equipped kitchen and cinema sized tv screen with Netflix/Apple TV. Convenient to ski slopes.

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 +)

Design Farmhouse w/ Pool + Firepit | Hudson Valley
A private, design-forward escape in Accord. One of the Hudson Valley’s most sought-after locations. BoHo Farm House is a luxe 3BR/3BA on 8 acres with a large dog-friendly fenced area. Recently renovated and featured in PureWow, the home offers vaulted ceilings, a light-filled open living space, chef’s kitchen, cozy fireplace, fire pits, and spa-like baths. Minutes from Inness, Westwind Orchard, Arrowood, and Stone Ridge, with easy access to hiking, skiing, and top farm-to-table dining. ⸻

Private Catskills Cabin Retreat w/Hot Tub
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!

Woodstock Historic Artist Estate- The Museum House
The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

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.
Fenced & Salt Water Pool | Cozy Catskills Cottage
The perfect spot to unwind with family, friends, and pups. Spend the day hiking, visiting farms, or trying local restaurants, then come home to the yard for kid-and-dog frolicking, “Squirrel TV” through long windows. Soak in the claw-foot tub or the jetted spa tub, then gather by the fire with wine and board games. Swim and make s’mores in summer, watch snow fall in winter, and enjoy peaceful views in every season, relax, play, laugh, repeat.

Spacious Catskills Farmhouse on over 5 acres!
Spring into fun in the Catskill Mountains! Enjoy a hike at one of our local trails or nature preserves. Try your luck at the casino, spend a day at the indoor water park, or play a round of golf at one of the local courses. You will feel right at home in this charming & restored 5BR farmhouse. Located on 5+ acres near the great Catskills Forest Preserve, this is a great place for four-season recreation.

MODERN FARMHOUSE in the WOODS
MODERN FARMHOUSE in the WOODS. 3 Bdr., 2 Bath. Very convenient to Saugerties and Woodstock. New 18' x 36' pool (Open Memorial Day through mid-September). Gourmet kitchen, hand-built stone fireplace, Child friendly. 3 beautiful acres, woods, and a big yard for grilling & fun. Swing set for the kids, stone fire pit for everyone! Washer & Dryer available for stays of 3+ days.

Ski & Sauna! Modern Mountain Escape
Welcome to a brand new Catskills getaway. Inspired by Japanese and Scandinavian design, every detail has been thought through to create the perfect private retreat where interiors blend seamlessly with the surrounding mountains. You’ll see high end finishes throughout the space and all the amenities you could desire. Welcome to a relaxing stay at your home away from home.
Popular amenities for Shandaken rentals with a pool
House rentals with a pool

Shula | Farmhouse | Hot tub, Fire pit, Pool

Gorgeous Villa MntnViews, POOL, hot tub, grill!

Scenic River View Escape | New Paltz

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

Modern Lux 5-Bed, Double Fireplace, Dogs Welcome

Upstate Modern Scandinavian Barn in the Catskills

6-Acre Lux Estate: Hot Tub, Fireplace, Near Skiing

Fawn Hill: Elevated Log Cabin w/ Year-Round Pool
Apartment rentals with a pool

Cozy Gem with Mountain Views

Windham Condo

Hideaway Windham/Hunter Fireplace, Snow & Skiing

4 Bedroom Condo, Close to Golf Courses and Biking

5-Star Lux Condo: Ski-In/Out, Heated Pool, Hot Tub

Luxury Ski in Ski out Condo + Amenities

Cozy Mountain Condo

Ski Windham Mountain ( Catskills, NY)
Other holiday rentals with a pool

Catskills Creek | Forest Views, Hot Tub & Pool

Newly Built Private Home & Pool

Woodstock Barn Artist’s Retreat in Bearsville

The Little Shelter at Gunks EcoLodge

Tranquil Retreat in Kerhonkson

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

Cold Brook Cottage

Converted Church w/Pool & Hot Tub – Hudson Valley
When is the best time to visit Shandaken?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $234 SGD | $230 SGD | $211 SGD | $203 SGD | $203 SGD | $244 SGD | $289 SGD | $284 SGD | $220 SGD | $274 SGD | $272 SGD | $275 SGD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
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 $103 SGD per night before taxes and fees

Verified guest reviews
Over 2,770 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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- Rentals with pools Ulster County
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- Resorts World Catskills
- Windham Mountain
- Howe Caverns
- Thacher State Park
- Hunter Mountain Resort
- Plattekill Mountain
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Taconic State Park
- Opus 40
- Benmarl Winery
- Storm King Art Center
- Walkway Over the Hudson State Historic Park
- Millbrook Vineyards & Winery
- Poets' Walk Park
- Mohonk Preserve
- Peekamoose Blue Hole
- Lake Minnewaska




