Cottage vacation rentals in Windham

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Windham

Guests agree: these cottages are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Superhost
A bright living area is furnished with a green armchair, a light wood coffee table, and a small dining table with chairs. Large windows allow natural light to fill the space, while a bookshelf displays various books and decorative items. A wall clock adds functionality.
Cottage in Stamford
4.88 out of 5 average rating, 124 reviews

Cozy Catskills Cottage

This is my new catskill cottage. We are proud to offer you the perfect place for your retreat with more than 4 acres of maple trees, streams, old stone walls, spring and sitting on a small hill. I put all my effort in creating the best place to spend a weekend or a full season (all four seasons are beautiful and with plenty of things to do in the Catskills). There are two bedrooms, one is actually a loft on the second floor open to the living area. All spaces are generous for this 840 sq ft house. you´ll love the areas including the kitchen and bath. Guest can access all areas. I´m not around sometimes but you can reach me on the Airbnb app msg or by email. Instruction on how to arrive will be sent a few days before. There's always somebody around to help in case needed. Discover the famous Northern Catskill region with its ski resorts, hiking trails, mountain biking, whitewater rafting, and American fly fishing. If food is on the agenda, Conde Nast Traveler called the region "New York's culinary retreat." Want to drop the car? you can get to the property by bus! From NYC: Just take the Trail ways bus to Oneonta NY, and it will drop you a few hundred feet from the house. Same back to the city!. You can get here by bus from Albany, Buffalo, Montreal and many other cities in the region. If you want to use this method of transportation, I can assist with more information.

Guest favorite
The living room features exposed wooden beams and warm hardwood flooring. A spacious seating area is centered on a large area rug, surrounded by colorful floor rugs. Framed artwork adorns the walls, while natural light filters in through window treatments.
Cottage in Catskill
4.95 out of 5 average rating, 106 reviews

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 :)

Superhost
A living area features a cozy gas fireplace framed by a white mantel. Comfortable seating is provided with a gray armchair, vibrant red chairs, and a green ottoman in the center. A dining table for two stands to one side, with artful wall decor enhancing the ambiance.
Cottage in Gilboa
4.91 out of 5 average rating, 325 reviews

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.

Top guest favorite
A cozy living space is highlighted by a light wooden floor and a white shiplap ceiling. A comfortable brown leather couch and an orange accent chair provide seating. A wooden coffee table sits in front of the sofa. Wall art and a floor lamp add warmth to the room.
Cottage in Kingston
4.93 out of 5 average rating, 393 reviews

Kapitan’s Cottage Private Upstate Catskill Retreat

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.

Top guest favorite
The cottage exterior is painted bright yellow, featuring blue accents. A small porch includes a table and chairs, surrounded by greenery. Decorative lights hang along the porch, with a welcoming entry door leading into the home.
Cottage in Catskill
4.96 out of 5 average rating, 299 reviews

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.

Guest favorite
An open-plan kitchen and dining area features a large wooden table surrounded by several chairs. A modern kitchen with dark cabinetry and stainless steel appliances is seen in the background. A wood stove is positioned near the window, which offers views of the snowy outdoor scenery.
Cottage in Saugerties
4.94 out of 5 average rating, 327 reviews

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.

Top guest favorite
A stone patio is surrounded by vibrant flowers and greenery, featuring a wooden table with four chairs. The cottage's large window provides a view of the inviting outdoor space, where additional potted plants add a touch of color and natural beauty.
Cottage in Chichester
4.99 out of 5 average rating, 605 reviews

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.

Top guest favorite
The cottage features a welcoming front porch with wooden pillars and a sturdy railing. A well-maintained deck leads to the entrance, with decorative planters and pumpkins adding charm. The dark exterior is complemented by light-colored window frames and an inviting doorway, framed by soft outdoor lighting.
Cottage in Haines Falls
4.99 out of 5 average rating, 156 reviews

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!

Superhost
Cottage in Hunter
4.79 out of 5 average rating, 139 reviews

The Cabin

Nestled in the heart of upstate New York, our comfortable cabin offers stunning views of nature and is just 5 minutes from Hunter Mountain—one of the top destinations for enjoying the vibrant beauty of autumn. Whether you're into hiking, skiing, or snowboarding, this is the perfect spot for your outdoor adventure. Located only 2 hours from New York City and just 15 minutes from Windham. Escape the hustle and immerse yourself in one of the most picturesque spots in upstate NY.

Top guest favorite
The cozy cottage is surrounded by a lush green lawn, with a wooden deck and twinkling string lights creating a charming ambiance. A vibrant flower bed with sunflowers adds a splash of color, while the nearby creek offers serene water views.
Cottage in Saugerties
5 out of 5 average rating, 414 reviews

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.

Top guest favorite
The exterior of Solheim Cottage is showcased, featuring a well-maintained lawn with stepping stones leading to the entrance. The cottage's dark exterior contrasts with the vibrant green trees and open meadow, with expansive windows offering views of the surrounding mountain landscape.
Cottage in Halcott Center
4.98 out of 5 average rating, 335 reviews

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.

Guest favorite
A cozy living area showcases a brown sofa adorned with decorative pillows, complemented by a patterned area rug. A rocking chair sits nearby, and a wooden table holds a stack of books. Natural light enters through two windows featuring bamboo shades.
Cottage in Phoenicia
4.95 out of 5 average rating, 302 reviews

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 #2025-STR-AO-084

Popular amenities for Windham cottage rentals

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Greene County
  5. Windham
  6. Cottage rentals