
Cottage vacation rentals in Windham
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Top-rated cottage rentals in Windham
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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.

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.

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.

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.

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.

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.

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!

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.

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.

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
Cottage rentals with a hot tub

Charming Cottage in Kingston - License #002740

Sip & Soak in the Heart of the Catskills

Tranquil Cottage in Catskill/Roxbury w/ Hot tub

Country Cottage w/ HOT TUB & Views

Dancing Bear Cottage

Hot Tub & Chic Catskills Woodstock Design Retreat

West Kill Cabin W/Hot Tub Art Flick's Mom's House

Ashokan ArtHaus, Private Hot Tub, Wags Welcome!
Pet-friendly cottage rentals

‘Clavashack’ Country Cottage

Woodstock Dog Friendly Cozy Cottage in Town + Yard

Hudson Valley Cottage

Peaceful Cottage-in Private 5-acre field

🌟Riverfront Cottage W/2 Bedrooms Catskills 🌟

Mountain views, mid-century style! 1 mile to town.

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

Swan Cottage with Expansive Hudson River Views
Private cottage rentals

Catskills Stream-side Home Hike & Relax

Cottage with Private Deck on 8 acres of Woods

Intimate Cottage on Private Estate

Direct streamside with private stream access

Cozy Cottage, just off exit 20, 1/2 hr to Hunter

Perfect Cottage On A Hill With A View

Blue Mountain Cottage

Catskills Getaway w/AC on 3 Acres near Woodstock
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- John Boyd Thacher State Park
- Howe Caverns
- The Kartrite Resort & Indoor Waterpark
- Glimmerglass State Park
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- Albany Center Gallery
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