Cottage vacation 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 :)

Cupcake Cottage! 1838 renovated barn, with views.

Spring has arrived! The flowers are popping up. Two night rentals are available from January-May. New 2026: Kitchen Aid Stand Mixer. 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.

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.

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.

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.

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 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.

Cozy Catskill Cottage on the Pantherkill

Cozy Cottage nestled in the Catskill Mountains minutes away from village of Phoenecia. This is a great secluded spot and easy to get to and conveniently located near great restaurants, skiing, hiking, tubing, fishing, swimming holes, Village of Woodstock. This small cottage feels bigger than it is while remaining cozy and intimate. Great getaway spot for couples or a solo retreat into the beautiful Catskill Mountains. License #2026-STR-AO-084

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.

Perch Cottages #9: Creek access + Sauna + Mt views

A group of modern cottages with spectacular mountain views, and magical creek frontage on the Esopus Creek (with its own beach and swimming hole!) Completely renovated. Quick 2 HR drive from the city. ✔ Fishing and Swimming ✔ 1 Dog or Cat per cabin allowed ✔ Gas BBQ Grill ✔ 40” Smart TV ✔ Bluetooth sound system ✔ Memory foam mattresses ✔ Onsite parking 7 mins → Ashokan Rail Trail 25 mins → Belleayre Ski Resort

The Cottage

Located just a short drive north of NYC, nestled between Woodstock and Phonecia, is a little cottage waiting to be discovered by you or you and a guest! This is a stand-alone cottage apart from the main house on the property with its own designated parking, so you get this entire private oasis to yourself.