Cottage holiday rentals in Windham

Cozy Catskill Cottage

Kick back and relax in this serene and stylish mid-century cottage. Perched atop a knoll and shaded by a giant oak, the enchanting property hosts a juniper grove, apple trees, wildflowers, wild raspberries and blackberries. The backyard oasis consists of a gravel picnic area, patio, firepit flanked by Adirondack chairs and ample grassland for yard games. Have your morning coffee on the front porch rocking chairs and take in the surroundings. This is a quiet place to relax, no parties please :)

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 open roads on a bicycle or visit Windham and Hunter villages. Find us on Instagrm @upstay z, #upstay z, #homealonemountain to learn more about the area.

1930's Cottage charm cozy air cond. near hiking

1 bedroom 1930's guest cottage with a living room. Near many hiking trails. Window air conditioner brand new, ceiling fans in living room and bedroom. Separate windowed bedroom with new full size mattress. Full size gas stove, microwave, fridge, Keurig coffee maker, toaster and large tiled counter and sink. Full bath off bedroom with large clawfoot tub and shower combination and sink and brand new toilet. Wifi , flat screen Smart TV. Vintage cast iron fireplace with electric insert.

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.

Fabulous Lemon Cottage in Rhinebeck, NY

This cozy, clean, and light-filled cottage with its bedroom loft provides a perfect getaway anytime of the year. When you do venture out, you're in the heart of it all; only a few miles from Rhinebeck village, but also close to Red Hook, Bard, Kingston, Woodstock, Hudson, etc. Use our guidebook to explore the area, or choose to stay in at this quiet, private cottage with views of the woods. LGBTQIA+ friendly. All people from all cultures and backgrounds, without exception, are welcome.

Cozy Catskills Cottage with Mountain Views

Beautiful home on 5+ acres in the Catskills Region! Enjoy the crisp air and mountain views while you relax near our firepit. Grill up some food and sit on the back patio with a view of the mountains surrounding you. At night enjoy the countless stars outside or hang out inside and put on the TV and get a fire going in our wood-burning furnace. Hi-Speed Internet & SmartTV which make for perfect work-cations! Quiet & safe neighborhood, dog-friendly, washer/dryer & fully equipped kitchen!

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!

Carriage House on Falls, Walk to Village

Welcome to 1903 Carriage House on the Falls — just down the hill from the vibrant village of Saugerties. This cottage blends modern comfort with rustic charm. Its cozy size makes it the ultimate escape for couples seeking a tranquil getaway. Admire panoramic creek vistas from the back deck. Enjoy the outdoors with a gas grill and waterside gazebo, unwind with board games, or relax with a movie on the SmartTV. As night falls, drift off to the soothing sound of the waterfall.

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.

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.

Evergreen Escape - Woodsy Artistic Retreat

Floor to ceiling murals thoughtfully painted by a local artist cover every wall to seamlessly blend the interior living pace and outdoor Zen. Relax on the covered front porch or the private back deck with a fire pit situated directly next to hundreds of acres of forest. Stroll through the trees and explore the nearby woods or relax inside with all the comforts you'd expect of a newly renovated home.