Cottage vacation rentals in Windham

Pawfect Family Retreat w/fenced-in yard & Dog Park

Welcome to the Pawfect Family Retreat- our dog-focused cottage in East Durham, NY! This cozy 2BR, 1BA home with a loft (3rd BR /sleeping area) is made for tail wags and happy hearts. Enjoy a fully fenced backyard with a private dog park, pup-friendly amenities, and cozy spaces for the whole family. Just minutes to Zoom Flume. Close to Windham(13 mi) & Hunter Mountain(18 mi), hiking, farms, breweries, and antique shops, town of Catskill & Hudson-your year-round getaway for unforgettable memories.

Cupcake Cottage! 1838 renovated barn, with views.

The Airbnb 15.5% service fee is now built directly into the nightly price. New for 2026: Kitchen Aid stand mixer, towels, frying pans. Cupcake Cottage has had a total renovation: the same light, charm, and views remain but inside there is a new kitchen, flooring, and heating system. And outside, a new deck and porch configuration, windows, siding, roof and dormers. The house is an 1838 barn with old beams and rafters, and modern finishes of hemlock, red oak, and western red cedar throughout.

New:Cozy Barn-Style Retreat Minutes From Woodstock

Recently featured in Vogue as one of “The Best Airbnbs in Upstate New York for a Weekend Away From the City” - A cozy getaway upstate on 2 acres of beautiful Catskill land. It's only 8 minutes to Woodstock, 5 minutes to the village of Saugerties, and there’s hiking, skiing and swimming within minutes. The entire second floor has been newly renovated including the bathroom and both bedrooms. The first floor is an open layout with kitchen, living and dining areas leading to the backyard deck.

Flat Rocks Cottage: Ski and Swim in the Catskills!

A year-round Catskills getaway! Located on one of the best swimming holes in the Catskills- known for its flat rocks. In the warm months, you can walk across the lawn scented with wild thyme, down the trail in the backyard, take a swim in the cool clean water of the Schoharie Creek and lay on the hot flat rocks. It is nature’s spa. In the winter, after a day of skiing at one of the many nearby ski mountains, nestle in by the fire, on our comfy couch, and cook in our well-equipped kitchen.

Catskills Retreat with Geothermal Cooling & Solar

Enjoy a peaceful retreat at the cottage, or use as a home base for exploring the Catskills. Family-friendly, private 4 bed, on a secluded 6.4 acre property. Enjoy coffee on the deck. Grill dinner and gather at the picnic table. Read on a blanket or lounge chair on the spacious private lawn. Relax by an evening campfire at the fire pit. Enjoy the living room fireplace, play board games, stream a movie. Or choose a more active Catskills adventure! Explore area hiking and swimming holes.

Garden Cottage In The Catskills

This quaint, relaxing cottage sits among Flowering Gardens in spring & summer, incredible Fall Foliage in autumn, & a Wonderland in Winter. Enjoy a peaceful cozy & private space with nature at your doorstep, an outdoor fire pit, stargazing, & your own stone patio at the edge of the woods. We love to share our garden, come pick your own! We are in the heart of The Catskill Mountains, 2 miles from the vibrant town of Phoenicia, in the hamlet of Chichester near the Stony Clove Creek.

Luxury+firepit+stream+walk/town=Brook Cottage Too

Brook Cottage Too occupies the west wing of a newly-renovated 1928 Woodstock artist’s cottage featuring: oversize north-light windows; skylights; 1 bedroom w/king bed; spa-like bathroom; newly-remodeled kitchen; fire stove; bluestone patio w/gas grill + firepit; AC. Ideally located at the end of a private lane on a spacious shared property bordered by a year-round stream + conservation land. Immaculately clean + available for long-term rentals, as well as short-term stays.

Pet friendly Cottage close to ski resorts

Pet friendly 2 bedroom cottage in the Catskills Mountain area. Kitchen, with updated appliances mid 2023, is equipped with an electric stove and new refrigerator. Gas grill on deck as well. Living room has a fireplace, TV, Wi-Fi, and a small dining area capable of seating 4 people. Outside has a large backyard with a lawn chairs, hammock and fire pit. Bathroom essentials are provided. Guest must bring wood for indoor fireplace. Check in and out times are flexible.

Cozy Cottage with Stunning Mountain Views

Welcome to Halcott Cottage! Featuring gorgeous mountain views, less than two and a half hours from NYC, and ten minutes from Belleayre Ski Center, this cozy and private cottage is perfect for a romantic couples retreat, two couples, a small family, or a group of friends looking for a relaxing and quiet escape in the historic Catskills. The cottage is a short drive to Phoenicia, Woodstock, Andes, and Margaretville for shopping, dining, antiquing, skiing and exploring.

Stream Come True | Hot Tub, Ski, Hike, Relax

Welcome to Flowing Water, a peaceful streamside cottage in the heart of the Catskills where the sound of rushing water and rustling trees melts stress away. Just minutes from Phoenicia and a short drive to Woodstock, Hunter, and Belleayre, it’s the perfect retreat for skiing, hiking, stargazing, or simply relaxing. Enjoy a hot tub or the firepit under the stars, a wood stove, streamside deck, and peaceful vibes year-round.

Stunning Woodstock 1 BR Hideaway

Find complete tranquility 5 minutes from Woodstock's bustling Village Green. This sun filled space is situated on a lovely 15-acre owner-occupied property with a private porch and bluestone patio which overlook the forest, seasonal stream and falls. Your only neighbor is the owner, a local painter and sculptor, who lives across the stream.

Peaceful Cottage With Mountain Views

Forget your worries in this tranquil cottage, located on Catskill Mountains. This furnished 2-bedroom home is the ideal place for those who have an appreciation of solitude and nature. The cottage sits on 1 acre of land, with a wooden patio overlooking the mountain - just the perfect place for meditating over afternoon tea.