Vacation rentals with a pool in Shandaken

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. 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.

Contemporary Guesthouse with Views and Privacy

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.

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 - Hammocks and much more!

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 +)

Hideaway Windham/Hunter Fireplace, Snow & Skiing

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Spruced Moose Lodge w. Hot Tub & open Pool to oct

*Pool Open Until Oct 21!* Secluded log home nestled in 5 acres of Catskill mountain forest, with 4 bedrooms & 3.5 baths (incl. basement with built-in full size bunks). Enjoy a sunroom, screened porch, pool+ brand new hot tub, projection screen home theater & a treehouse that resembles a floating pirate ship 30 feet up in the trees. We renovated the kitchen & master bed with new walls of windows in May - pics to come! Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Catskills Retreat: 4Br l Fire-pit l Hot Tub l Hike

7 min drive to Phoenicia 10 min drive to Belleayre 25 min drive to Hunter 35 min drive to Windham Renovated 1920’s cabin style home nestled on 4 acres in the Catskill Mountains. Easy to get to and conveniently located near great restaurants, skiing, hiking, tubing, fishing, and swimming holes. A ton of outdoor space to enjoy in addition to our fully private seasonal pool (Late May-Sept). 6 person hot tub is available year round. Not for parties!! Please be mindful of our neighbors!

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.

Country Cottage w/ HOT TUB & Views

Welcome to the most peaceful and tranquil place in the world. Our beautiful home is situated on 3 acres of private land with a private pond and incredible views of the mountains. Escape your life and stressors, and come stay in the fresh air where all you will hear are birds chirping - no sirens, cars or people. The cottage is fully stocked to be enjoyed for all 4 seasons! Relax in the hot tub, or go for a swim in the pond. Our property is the perfect vacation getaway.

Only Ski In Out on Mtn | Hike, Golf, Fish, Relax

Mountainside 1 bedroom cabin that fits 4! Ski on/off Hunter Mountain right from your doorstep. Enjoy hiking within a 5-minute drive or walk right onto the mountain from your porch. Unbeatable location on Hunter Mountain, short drive to the picturesque, colorful village of Tannersville, majestic Kaaterskill Falls, and renowned fishing! Fully stocked kitchen/bathroom, full entertainment system with streaming, high-speed WiFi, and dedicated work space.

Ski & Sauna! Modern Mountain Escape

Welcome to a brand new Catskills getaway. Inspired by Japanese and Scandinavian design, every detail has been thought through to create the perfect private retreat where interiors blend seamlessly with the surrounding mountains. You’ll see high end finishes throughout the space and all the amenities you could desire. Welcome to a relaxing stay at your home away from home.