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

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.

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.

Scenic River View Escape | New Paltz

Unwind in nature. House is located on the river bank with river views and surrounded by tall trees with a huge porch and private backyard. The house was recently renovated with all the modern amenities. The place breathes with tranquility and peace and was stylishly decorated with a lot of care and consideration to guests' experience by an experienced host. Just come as you are and enjoy as we have all you need here including top notch complimentary tea, coffee, yoga mats and much more

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..

Light-Filled Upstate Home, Perfect Location

Located just south of the Catskills in the beautiful Rondout valley, under 2 hours away from Midtown Manhattan, The House On Smith Lane was built in the modern farmhouse style. Striking the perfect balance between classic and comfortable, our home is equipped with fully modern amenities, including state-of-the-art kitchen and appliances, nest thermostat heating system, and an in-ground pool with bluestone coping (pool is open from Memorial Day to Labor Day). @thehouseonsmithlane

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.

Perfect Summer House 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.

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.

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.

Cozy Catskills Escape: Sauna, Animals, Mt Views

Make the most of winter’s final weeks and take a break upstate. Escape the city bustle for a cozy, restorative stay at Napping Horse Farm! The Bird's Nest is a light-filled retreat nestled on 30 secluded acres at the foot of Overlook Mountain. Perfect for couples, solo travelers, and small families seeking wellness, stillness, and a memorable experience with rescue farm animals. Nature, comfort, and deep calm just 2 hours from NYC.

Kapitans Cottage Private POOL Minutes to Kingston

Soak up summer at this cozy vintage Catskills retreat with an in-ground saltwater pool (mid-May–Sept). Just minutes to Kingston, High Falls, Stone Ridge- restaurants, shops & farmers markets, plus miles of hiking trails, rail trails & swimming holes across the Hudson Valley. 2BR, 1.5BA with private yard, stone deck, fire pit & BBQ. Pet-friendly, peaceful and perfect for couples, families or midweek escapes. Generator on-site.