Holiday rentals with a pool in Ulster County

Contemporary Guesthouse with Private 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.

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.

Kapitan’s Cottage: Private Retreat with Salt Pool

A vintage rustic country retreat with two floors with modern amenities. 2BR, full & half bathroom. Family & Pet friendly. Large yard surrounded by a mature tree line for secluded privacy. Private stone deck w/ fire pit, BBQ & comfortable deck furniture. Summer Pool access and Generator on site. Close to Kingston, High Falls, Stone Ridge and Woodstock yet just far enough out to feel you're away from city hustle and bustle. Close to miles of hiking, outdoor activities, parks & Ski slopes.

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..

Pool - Hot Tub - Game Room - Mini Golf - Country

Welcome to our renovated Catskills oasis on the Rondout Creek and Rail Trail, minutes from Minnewaska and the Gunks! Unwind in the year-round covered hot tub, lounge by the pool, gather around the fire pit, or play mini golf under the stars. Inside, relax by the fireplace or hit the speakeasy-style game room with pool, ping pong, Pac-Man, Pop-a-shot, darts, a bar, and TV. We offer private chefs, local meats, and top picks for hikes, bites, and watering holes. Yes, we love pets! 🐾

Secluded Home: Pool, Sauna Tennis & Trails

Welcome to your perfect all-inclusive Catskills getaway. Secluded hilltop cabin in the woods. Cozy home features heated pool, sauna, large 2000sf deck overlooking forest, full size tennis court, 15.5 acres for hiking, fishing, and exploring. Located only 2 hours from New York City & 20 mins from Woodstock. Two-bdrm house with one full bathroom and loft sleeping space. House is located on a quiet road. Turn into the private driveway and get ready to relax and mingle with Mother Nature

Beautiful Salt Water Pool & Fully Fenced 10 Acres

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

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.

Seclusion and Romance - Pool is open and heated!

Amazing 5 Star guest house. Pool is open and heated! Outdoor living room with a wood fireplace. Close to many attractions: hiking, wineries, breweries, restaurants, Sam's Point, etc. Romantic, high end getaway. Amenities: charcoal BBQ, mini fridge, propane grill, full bath, microwave, wood fireplace, fire pit, single induction hot plate, wifi, smart TV, Firewood and fire bricks available.