Holiday rentals with a pool in Esopus Creek

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

4.94 out of 5 average rating, 399 reviews

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.

An aerial view captures the red dairy barn, featuring a colorful roof with decorative elements. Surrounding greenery and open fields create a serene backdrop, while a winding path leads to the barn entrance, inviting exploration of the surrounding landscape.

4.99 out of 5 average rating, 279 reviews

The Woodstock Barn House - Sauna, Gym, Jacuzzi

19th Cent Hand-Hewn Dairy Barn. LOVE BIG GROUPS - if your #s exceed 10 we can accommodate. Pet Friendly Inquire for summer dates! IG: @woodstockbarnhouse 2 guest 1 night stays inquire for clean discount Travel & Leisure "Gorgeous Old Catskill Barn" House Beautiful "Best Upstate New York Weekend Destinations " Pool about May to midOct Hot Tub - all year Gym Sauna Fire Pit Projector Tv Pizza Ovens Cabana Kitchen 2 miles from center of town. *No checkin avail Tgiving, Xmas Day, Easter Sunday

4.88 out of 5 average rating, 221 reviews

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

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

A panoramic view of distant mountains stretches under a clear blue sky. The landscape features a mix of trees and open areas, showcasing the natural beauty of the surroundings.

4.88 out of 5 average rating, 154 reviews

Gorgeous Villa Mntn Views • POOL • hot tub •grill!

POOL NOW OPEN!! 5/8/26 Our beautiful Villa has amazing mountain views, a clean, modern design & is the perfect getaway to socialize & relax. It is ideally located for hiking & has a gorgeous, private heated salt water pool (mid May- mid Oct) & a wonderful hot tub which is open year round! It is on a pvte, quiet road 5 mins to town. In addition to the 3-bed, 2-bath main house there is a spacious studio cottage with full bathroom, heat/AC that can be used as WFH pvte office w/ high speed internet.

4.97 out of 5 average rating, 176 reviews

A spacious living area features two modern armchairs with orange accent pillows facing a large picture window. The serene view of the wooded area surrounding the private pond is visible, inviting natural light into the space. A low coffee table occupies the center, complemented by a soft sofa nearby.

Cottage in Saugerties

Black Ridge Cottage: Pond, Cowboy Pool & Sauna

Kick back and relax in this calm, stylish space, with private wildlife filled pond & cowboy pool This house is great for a family, or two couples. There are lots of relaxing spaces inside and several seating areas in nature outside. Ten minutes to the towns of Woodstock and Saugerties, you will have the perfect location to enjoy the best experiences the Hudson Valley has to offer. This 4 bedroom, 3 bath house has been recently gut renovated. Enjoy the beautiful design and natural landscape.

4.98 out of 5 average rating, 122 reviews

Home in High Falls

Comfortable & Spacious Country Home - All Seasons

We welcome you to stay at our inviting home in the hamlet of High Falls. The two-story early 1900's era farmhouse is set on 12 private acres off a quiet country road in a lovely residential area. Grounds feature access to woods, pond and canoe-ready Roundout Creek. A large sunlit family room, a variety of games, vast outdoor space with furnished patio, in-ground pool/deck/BBQ/swings/firepit/hammock offer the perfect place to relax and restore your connection to nature, friends and family.

5.0 out of 5 average rating, 172 reviews

An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.

Home in Saugerties

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.

4.98 out of 5 average rating, 129 reviews

An aerial view captures The Evergreen retreat set on three acres, showcasing a spacious yard surrounded by trees. A heated pool is visible beside a patio area with a dining table, while a fire pit is centrally located, enhancing the outdoor experience.

Home in 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.

4.97 out of 5 average rating, 130 reviews

Woodstock Family Home w/ Tree House + Heated Pool

Town of Woodstock Special Use (aka STR) Permit #23-0683. Featured in Hudson Valley Style Magazine, this fully updated modern farmhouse is ready to host. Radiant-heated full baths, whole-house generator, PRIVATE heated saltwater pool (schedule/weather permitting), four-season porch, indoor fireplace, fully equipped kitchen, outdoor grill, etc. Basement includes ping pong and pool tables. All bedrooms and full baths upstairs. Half bath on the main floor. Dogs are not permitted at any time.

4.9 out of 5 average rating, 144 reviews

Chalet in Ruby

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

4.91 out of 5 average rating, 117 reviews

Cabin in Kingston

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.

A refreshing swimming pool is surrounded by a wooden deck adorned with colorful flower pots. Comfortable lounge chairs offer a place to relax under a blue umbrella while a table invites outdoor dining. Lush greenery envelops the area, providing a private and serene setting.