
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.
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.

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

Contemporary Guesthouse with Heated Pool
Secluded studio on 13 acres in Bearsville with views of meadows, mountains and woods. Stand-alone guest house with queen size sleeping loft, kitchenette, fully tiled bathroom, elliptical trainer, and all amenities. Wake up in the morning and enjoy the amazing views with your coffee, hike in the woods, or meditate at the waterfall. In season enjoy the completely private heated pool. End the day with s'mores around the fire pit. An ideal getaway from the city yet only three miles to Woodstock.

Viewtop Farmhouse-Relax & enjoy summer by the pool
Enjoy View Top Farm House, a rustic, 100+ yr old, farmhouse/former boarding house on 3 beautiful acres, overlooking the Catskill mountains. Enjoy time on the patio by the fire, barbecuing, eating alfresco or swinging in the hammock. Its 15 min to the Rondout, 7 min to the Village of Saugerties. Get breakfast, lunch or dinner out, or cook at home in the large, well stocked kitchen. Minutes from restaurants, antique stores, hiking, and biking. Enjoy many amenities. Well behaved pets are welcome.

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.

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.

Enchanting Upstate Cabin w Pool, Firepit
Welcome to our family-friendly haven in the heart of the beautiful Hudson Valley, just 10 minutes from Kingston, Saugerties, and Woodstock. Less than 2 hours from New York, our retreat offers an idyllic escape surrounded by enchanting forest views. Great for large groups, and year round stays with a heated pool and air conditioning in summer months. Just 40 mins away from skiing Hunter. Listing pics by @dirtandglass and @heypamcakes See more snapshots @theserenityhomes on IG

Lovely country house; stunning view
This 100 year-old home on 83 acres overlooks a beautiful meadow, surrounded by dogwood and maple trees -- breathtaking in spring and fall. The saline pool is open generally between April and October, and surrounded by an abundance of flowers. In the cooler months, an atmospheric wood-burning fireplace makes the cottage cozy. This property is the subject of a book A FIELD OF MY OWN: A Memoir of Place. Please note that 35-40% of the price is fees and taxes from this site.

Peaceful Hudson Valley Getaway
Best for families! Relaxing and playful retreat! Come for the hiking, antiquing, HITS shows, farmer's markets, visits to Bard College! Especially KID FRIENDLY with all the necessary amenities. Enjoy the pool, deck, gas grill, fully stocked kitchen, bikes, hammock, fire pit, and open floor plan for gathering and home cooked meals. Feel free to message me if you are looking for specific dates that are marked unavailable. From June - August, 3 night minimum.

Modern Fall Getaway in Kingston - 1.5hr from NYC
Split-level 5 bd 3 ba home with a private pool, BBQ grill and fire pit. We have a fully stocked kitchen, children's items & are just 5 minutes from town. We‘re looking to share our home as a peaceful retreat with families and quiet groups only as we have neighbors close by. This is our personal home and we have a no-shoe policy. We kindly ask that you pass on this house if you are not comfortable with this. 1 pet under 35 lbs allowed with a pet fee.

Luxe modern A Frame, Hot tub and new heated pool
Experience the luxury of this black double A-frame, finished to the highest standards and nestled in the woods for ultimate privacy. The main bedroom features a soaring ceiling and spa-like en-suite with walk-in shower, tub, bidet, double sink, and heated floors. The sunny second bedroom also has an en-suite. Enjoy a chef’s kitchen, double-sided fireplace, hot tub, and a new pool available June. Pets must be disclosed and approved prior to booking.

Luxury Retreat with pool in historic Kingston
This historical brick building turned into a private residence on the Hudson River is your luxury retreat with top-notch amenities and finishes; perfect for a getaway weekend and longer stay. The house is 7 min walk from the marina and restaurants in the historic district of Kingston and seconds from the Hudson River. Perfect location for hiking lovers, boat lovers, and nature lovers.
Popular amenities for Ulster rentals with a pool
House rentals with a pool

midcentury mod * POOL * walk out trail R2R/Mohonk

Scenic River View Escape | New Paltz

MODERN FARMHOUSE in the WOODS

Saugerties Luxury -Pool, Fire Pit, Close to HITS

Highwoods Haven | saltwater pool and hot tub

Entire Home, Private Indoor Pool

Woodstock Getaway - Heated Pool/Hot Tub/FirePit
Fenced & Salt Water Pool | Cozy Catskills Cottage
Condo rentals with a pool

StunningViews•Bright2BR•Pool•NearFarm•Lakes•Farm

Cozy Gem with Mountain Views

Windham Condo

Cozy Mountain Condo w/ Pool

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

Hideaway Windham/Hunter Fireplace, Snow & Skiing

Luxury Ski in Ski out Condo + Amenities

Cozy Getaway Gem for 2 at Windham Quads.
Other vacation rentals with a pool

Modern Upstate Cabin, near Rhinebeck NY

Panoramic Mountain Views!

Sweet Fern Cottage With Saltwater Pool

Cottage with Private Deck on 8 acres of Woods

Woodstock Mountain Cottage w/ Swimming Pool

Little Farm Stay Catskill

Mtn View Lux Dome w/ Heated Plunge Pool

Modern Barn on 12 acres w Sauna, FirePit+swimming
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Resorts World Catskills
- Windham Mountain
- Catamount Mountain Ski Resort
- June Farms
- Butternut Ski Area and Tubing Center
- Plattekill Mountain
- Taconic State Park
- Thacher State Park
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Storm King Art Center
- Kent Falls State Park
- Hunter Mountain Resort
- Mohonk Preserve
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Peekamoose Blue Hole
- Storm King Art Center
- Millbrook Vineyards & Winery





