
Vacation rentals with a pool in Ulster
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Ulster
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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

Modern Upstate Cabin, near Rhinebeck NY
[ 🏊🏽♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

chezbevet-country cabin retreat
Town of Woodstock, NY permit No: 19H-017 Country Cabin Guest House Retreat in beautiful Woodstock, NY.Nestled in the mountains, near waterfalls and streams,3 miles from Village Green,5 min. from The KTD Monastery,10 min. from OPUS40 and HITS.Shopping,restaurants,skiing,hiking and the ambiance of Woodstock in the Catskill Mts.1 mile from Grammy Award Winner Levon Helm’s Rambles.Enjoy Maverick Concerts,Woodstock Playhouse and Historic Byrdcliff.The beautiful inground saltwater pool is now open

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.

Hudson River views with pool and hot tub
The Riverview Terrace House is located in a quiet neighborhood in Kingston NY overlooking the beautiful Hudson River. Just an hour and forty five minutes from NYC it is the perfect get away for family and friends. We welcome you to enjoy the house with 5 bedrooms, 2.5 baths, a pool open during summer months thru Labor Day and a hot tub open year round. Centrally located between uptown Kingston and Rhinebeck you will have access to the all of the great amenities the area has to offer.

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..

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.

The Little Shelter at Gunks EcoLodge
Now open in Winter, but subject to refunded cancellation if Snow makes the driveway unpassable for those without 4 or all wheel drive. This rental is a small cabin in the woods of New Paltz, NY. The cabin sleeps 4 with 2 twin beds in the loft and has a pullout couch with a quality queen size mattress. The kitchen is equipped but does not have an oven. Streaming TV and Internet. Check out our other listings at the EcoLodge, with Private Rooms/Baths, on the "About Me" page.

Secluded peaceful loft in barn by woods
La Barn Bleue sits on top of a hill by a forest, in a secluded and peaceful property. The main house, where we live is 150 feet down the hill. The apartment sleeps up to 4 people. The bedroom/lounge loft has one king bed and 2 twin beds. Ideal for families and kids above 5 years old. Because we use a rope railing, we cannot host kids under 5 years old for security reasons. We offer Wifi, AC/heat split unit, outdoor Picnic table, bbq, petanque court and pool!

Tyrolean Style Country House in Saugerties, NY
Tyrolean style, two family house on two acres, (owner and family are onsite and lives in the bottom unit) fully furnished 3 bed, 2 bath home, fireplace. AC in master and living room only. WIFI throughout. Guests have separate parking, entrance, back deck with a big table & 8 chairs. The house is newly renovated, new luxurious bedding in each bedroom. Wake up surrounded by trees and to a beautiful sunrise. Perfect for a romantic weekend or family vacation.

The Harvest Guest House~ Hidden Gem with Pool
Reconnect with yourself & nature. The Georgian style home is set on 6 wooded acres and surrounded by rugged rock ledges, minutes to Marist, The Culinary, Roosevelt & Vanderbilt estates. THE HARVEST GUEST HOUSE offers a genuine Hudson Valley stay. Your suite has its own private entrance, bathroom & fireplace. Enjoy a comfortable place to unwind after exploring nearby trails, river towns, and historic sites. Relaxed, real, and rooted in nature.

Airy & Private Escape on Mountain Rest Road *Pool*
Relax and unwind in our bright and private 2BR apartment located at the edge of Unison Arts Center’s sculpture garden (paths through woods and fields). A mile from New Paltz on the way to Mohonk Preserve, this simple but comfortable space features work by local artists and regional photographs. One of the bedrooms has an additional half-bathroom with a hand-made mosaic. Guests have their own entrance.
Popular amenities for Ulster rentals with a pool
House rentals with a pool

Saugerties Luxury Close to HITS, skiing, hikes

midcentury mod * HOT TUB * walk out trail 2 mohonk

Woodstock Family Home w/ Tree House + Heated Pool

Catskills SKI HAUS Winter Wonderland

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Gorgeous Villa MntnViews, nr SKI, firepl, hot tub!

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

MODERN FARMHOUSE in the WOODS
Condo rentals with a pool

Cozy Gem with Mountain Views

Windham Condo

Luxury 3-bedroom Condo on Windham mountain

4 Bedroom Condo, Close to Golf Courses and Biking

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

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

Luxury Ski in Ski out Condo + Amenities

Cozy Mountain Condo
Home rentals with a private pool
Magnificent Hudson River Estate with Infinity Pool and Spa

Rhinebeck Country Living with a Modern Twist
Fenced & Salt Water Pool | Cozy Catskills Cottage
Catskills Winter Ski Retreat – Near Belleayre!
When is the best time to visit Ulster?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$52,793 GYD | G$62,183 GYD | G$53,419 GYD | G$43,194 GYD | G$72,825 GYD | G$80,546 GYD | G$102,248 GYD | G$125,827 GYD | G$68,443 GYD | G$78,877 GYD | G$83,468 GYD | G$83,468 GYD |
| 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 vacation rentals with a pool in Ulster

Total vacation rentals
Explore 40 vacation rentals in Ulster

Nightly prices starting at
Ulster vacation rentals start at G$20,867 GYD per night before taxes and fees

Verified guest reviews
Over 2,370 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
40 of Ulster vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Ulster rentals

4.9 Average rating
Ulster stays are highly rated by guests—averaging 4.9 out of 5!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Thunder Ridge Ski Area
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- Resorts World Catskills
- Thacher State Park
- Windham Mountain
- Hunter Mountain Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Kent Falls State Park
- Plattekill Mountain
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Bear Mountain State Park
- Taconic State Park
- Norman Rockwell Museum
- Opus 40
- Berkshire Botanical Garden
- Naumkeag




