Cottage holiday rentals in Windham

Creekfront Cottage between Phoenicia & Hunter Mtn.

Built in the Summer of 1929, Stony Clove Cottage is nestled in the woods on a beautiful mountain stream, the Stony Clove Creek. It is a magical place suited for folks ready to turn their phones off. In 2021, wifi was added to this once landline-locked retreat so guests can remotely work or study in the woods. Bluetooth speakers are outside, and a turntable, with albums ranging from Rodgers & Hammerstein to Laura Nyro to Ralph Stanley, is available inside. And a wall of movies. And books....

Kapitan’s Cottage: Private Retreat with Salt Pool

A vintage rustic country retreat with two floors with modern amenities. 2BR, full & half bathroom. Family & Pet friendly. Large yard surrounded by a mature tree line for secluded privacy. Private stone deck w/ fire pit, BBQ & comfortable deck furniture. Summer Pool access and Generator on site. Close to Kingston, High Falls, Stone Ridge and Woodstock yet just far enough out to feel you're away from city hustle and bustle. Close to miles of hiking, outdoor activities, parks & Ski slopes.

Home Alone Mountain

Home Alone Mountain is a cozy cottage in a peaceful country setting. The house beautifully located in the small vacation community with a mountain view. Enjoy the privacy and tranquility of the 1,5 acre meadow adjacent to the state forest, take on the stroll in the woods, wander around the historic villages, take a swim in the pond, enjoy the country roads on a bike or visit Windham and Hunter village. Find us on Instagrm @upstay z, #upstay z, #homealonemountain to learn more about the area.

The Cottage on Sylvester Street

The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.

Cozy Mountaintop Cottage for a Catskills Escape

Enjoy your morning coffee on the sun porch with a glimpse of the mountains over the forest, curl up with a book as light streams through the picture window, roast s’mores over the fire pit surrounded by mountain woods, grab the guitar off the wall and accompany the piano, or relax in the large soaking tub. Take a short drive to find trails, slopes, and some of the best shops and restaurants the Catskills have to offer. This cozy cottage is the perfect spot to unwind and explore all at once.

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.

The Kaaterskill Cottage - views of Hunter Mtn!

Enjoy the serene environment of the Catskills from our recently renovated 1910 cottage. Our home offers privacy, comfort, and convenience in a prime location for anyone looking to explore. We are located less than a half mile to Kaaterskill Falls, and nearby to great hiking and skiing destinations. Our space has been set up with love and attention to detail, comfortably sleeps 6 adults and is family friendly. We welcome you to our cozy cottage in the mountains - make yourself at home!

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.

Cozy Cottage with Stunning Mountain Views

Welcome to Solheim 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.