Vacation rentals with a pool in Ulster

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

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.

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.

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.

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

Welcome to The Evergreen, our Catskills retreat located 5 minutes from Woodstock village. Sitting on 3 acres amongst the trees, this property boasts beautiful outdoor space with a heated pool*, hot tub, outdoor dining area, grill, and a fire pit, creating the perfect setting for relaxation and entertainment. This charming property offers 5 bedrooms & 3 full bathrooms, perfect for large families or groups of friends. It also features a study, ideal for those who need to balance work and play.

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.

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

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 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.

Upstate Getaway btw Rhinebeck+Hudson

Our home is located on an unpaved, private road in a quiet area and features an in-ground, heated, saltwater pool open between Memorial Day and Late September. In 2026, the pool will be available for bookings 5/22 - 9/18. A quiet and private getaway in the Hudson Valley and convenient to many popular activities. NOTE: For bookings during pool season, guests will be asked to review and agree to the safety rules relating to the pool.

Bluestone Escape - Where everyone is at home.

Bluestone Escape is a thoughtfully curated home designed by NYC interior designer Rhobin DelaCruz. Each decision was carefully made with comfort and style as the foundation of all choices. Bluestone Escape isn't just another rental, it's an experience. From hand picked artwork to the simpler detail of USB enabled outlets, Bluestone Escape will feel like the second home you are glad you have.

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.