Holiday rentals with a hot tub in Great Barrington

Epic architectural masterpiece w/ views & hot tub

This magical home in the Catskills mountains seamlessly blends the styles of a timeless mountain cabin with a modern industrial loft to create a uniquely jaw-dropping space. Nestled in the woods with mountain views, you’ll have all the space and quiet you’ve been craving. Boasting an entire glass wall of windows in the living room, the space is flooded with nature’s light. A cup of coffee in front of this view is a Zen experience. A distinctive wood-burning fireplace provides warmth & ambiance.

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

Serene Retreat w/ Cedar Hot Tub & Fire Pit

Whether you’re planning a couples getaway, a trip with friends, a family vacation, or even a solo escape, The Woodstock Retreat is your home away from home in the Catskills. Located just 5 mins from Woodstock, 10 mins from Saugerties, and surrounded by endless dining, shopping, and outdoor activities. Two separate bungalows, a handmade cedar hot tub, fire pit w/ Adirondack chairs, and hammocks are just a few of the features that make The Woodstock Retreat special. IG: @thewoodstockretreat

Secluded Artist's Retreat with Hot tub

Our well-equipped cabin sits at the end of a dead-end road on three secluded acres including rolling lawn, woodlands, and a pretty pond. You probably won't hear another car all weekend. Yet we are less than five miles from Woodstock, the cultural center of the Catskills, with its galleries, theaters, festivals, restaurants, concerts, and boutiques. Soak in our year-round hot tub, or relax on our extensive decks and screened-porch. You may not get back in your car all weekend!

Treetop Hideaway in Tyringham

For your upcoming stay, look no further than this airy, secluded log cabin overlooking the beautiful Tyringham Valley. On the first floor, you will find a great room with vaulted ceilings and a fireplace, as well as a master suite, second bedroom, half bath and recently renovated kitchen. The second floor includes two more bedrooms and a bathroom. The exterior offers a screen porch with hot tub, wraparound deck and 35+ acres of woods bordering conservation land in Monterey.

Best of the Berkshires + Hot Tub by Evergreen Home

Ski, hike, shop, and dine with this beautiful 2-bed, 1-bath Berkshires cottage as your home base. 7 minutes to downtown Great Barrington, this stylish, cozy rental has everything you need for a great getaway. A new renovation brings modern amenities to this classic 50’s cottage. Enjoy a chef’s kitchen, 500 sq-foot deck with hot tub, and thoughtful touches like yoga mats, a record player, board games, and a backyard hammock. Monthly ski rental discounts are available!

Green Acres Hawley Upper Studio (Bonus Room)

This space is a Large Studio Apartment in the Bonus Room above the Garage of a large log home overlooking Berkshire East Mountain Resort. Guests have shared access to the hot tub, deck, fire pit barbecue area and limited access to host's laundry facilities. You'll have sole access to the bonus room, deck & grill and full private bath. Space is comfy and charming, accessible from a private staircase or spiral into the main house's entrance hall.

Cabin Oasis near Town

Greetings and welcome to our delightful, recently remodeled cabin, seamlessly combining modern coziness with the allure of rustic charm. Situated within a welcoming Catskills neighborhood, this snug haven ensures an authentically comfortable escape. Step through the door to uncover a welcoming, well-planned interior that caters to your home-like needs. Savor your morning coffee on the deck or indulge in a soak in your exclusive hot tub.

Romantic getaway!3bdr/2bth-HotTub/Sauna/Fireplace!

Welcome to The Camptons Cottage! Spending time at a stylish, fully renovated cottage can be a great way to have fun and create lasting memories. Enjoy the cozy atmosphere, explore the surroundings, and engage in activities that everyone will enjoy. Whether it’s soaking in the HotTub, enjoying backyard, playing games, having a barbecue, or simply relaxing together. This is pet friendly house (only one pet allowed per stay). Thank you!