Vacation rentals with a pool in Catskill Mountains

Woodstock Mountain Cottage w/ Pool and Mtn Views

This romantic 2 bed cottage has large beamed ceilings, fully stocked kitchen, bathtub, mountain views, and hiking trails. We use strict cleaning protocols to ensure each stay is perfect and feels like home. The house is equipped with fast wifi and a ROKU Ultra for all of your tv needs! Located just 3 mins driving to the center of Woodstock. Swim in the pool, hike a nearby trail, enjoy nature, grill or relax in the hammock. Pool is shared with hosts. No guests of guests allowed and no parties.

Bella Cottage w/Pool, BBQ - Catskill Getaway

** Pool opens May 8 weekend! It is an above ground heated pool, the temp preset to 84 Disconnect, relax and rejuvenate in this cute country home! Enjoy the serene, wooded surroundings as you watch deer trot by and end your day unwinding under starlit night skies. This 2-acre gem is tucked away on a private drive, just off the main road. Though secluded, grocery stores and restaurants are just down the street. The house is equipped with all the modern amenities to make your stay comfortable.

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.

Luxury Prvt Estate w/Hot Tub+Gameroom nr Rhinebeck

Perched at the top of a hill on 20 private acres, this upscale, modern log home serves as an ideal home base to discover the picturesque Hudson Valley. The Hammock Hill House offers guests upscale features such as heated gunite pool, Sonos speakers, and a gourmet kitchen complete with Wolf and Miele appliances. A lower level lounge promises hours of fun with a full-size pool table, darts, and classic board games. Either the hot tub or the firepit are a perfect end to a busy day of exploration.

Mtn View Lux Dome w/ Heated Plunge Pool

This luxury dome is a modern home perched on a mountain top. Our aim is to combine the comforts of a large hotel suite with all the healing qualities of nature. Venture out or hike our own trails leading to a pond and a stream in the woods. Suited for long term WFH stays! We have Fiberoptic internet (ethernet avail) and plenty of space for your setup. Stroll the property at lunch or jump in the heated plunge pool between calls. Ask me about a special offer for long term stays. (14 days +)

midcentury mod * POOL * walk out trail 2 mohonk

A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. IN GROUND SWIMMING POOL & HOT TUB short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk to an organic farm? A scenic mile to R2R trail to Mohonk, Water St. mkt & the Village of NP WHOLE PLACE IS YOURS HOUSE & PROPERTY POOL May 1 -Sept 30 HOT TUB YEAR ROUND

Experience The Zen House

Enjoy your own private indoor movie theater with 7.1 Klipsch Premiere Surround Sound and leather recliner seats, a spa with a cold plunge pool & sauna, and a hot tub to reach the maximum level of relaxation. Play a game of ping pong, enjoy the fireplace outside and inside along with 5 acres! Amenities Include: - Hot Tub - Bath House with Sauna & Cold Plunge Pool - 12 Person Theater with immersive visual & surround sound + recliners - Game Room - Outdoor Fire Pit - Hammock & 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..

Contemporary Cabin w/ Hot Tub, Lake & Fireplace

Ticking all the boxes, this beautiful cabin has everything you could want for your retreat from city life! Five acres of private forest encapsulates the perfect seasonal mood as you step from the great room onto the huge wrap-around deck. Relax and enjoy the property with its hot tub, fireplace, A/C, BBQ grill and poolside loungers. For the adventurous at heart, check out the community shared lake access (non fishing), rivers, hiking trails and ski stations right at your fingertips.

Secluded Woodstock Retreat -Heated Pool and Sauna

Stunning, tranquil mountainside retreat with exposed beams, heated saltwater swimming pool, sauna, fireplace, soaking tub and rain shower. Situated on a 5-acre wooded hilltop, a ten minute drive to Woodstock and close to miles of walking trails. Roast marshmallows on the fire pit, flip burgers on the charcoal grill, and enjoy one of the best stargazing spots around. Indoors, find a well equipped kitchen and cinema sized tv screen with Netflix/Apple TV. Convenient to ski slopes.

BoHo Scandi Farm Retreat, Fireplace, Dogs Welcome

BoHo Farm House is a luxe, stylish 3BR/3BA retreat on 8 scenic acres in Accord, Hudson Valley—with a fully fenced area for dogs to roam safely. Featured in PureWow, this Scandi-style escape includes vaulted wood ceilings, large open living space and chef’s kitchen, cozy fireplace, fire pits, and spa-like ensuite bathrooms. Close to incredible hiking, skiing, and farm-to-table dining. Dog-friendly luxury meets fall and winter serenity!

Catskills Farmstay: Pool, 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.