
Vacation rentals in Windham
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Top-rated vacation rentals in Windham
Guests agree: these stays are highly rated for location, cleanliness, and more.

Catskill Mts Artist Cabin Hike Ski Dine Firegaze
Here Now ! Spring hikes w/roaring streams and falls, dining, mrkts, stars, firegazing. Our storybook cabin is privately nestled in the heart of the Catskill Mts, near seasonal stream and lake, under open sky surrounded by forest. Enjoy very nearby skiing; Windham and Hunter Mts, hiking, dining, antique, farm mkts. Experience true quiet, endless stars, staring into a wood fire, w/complimentary firewood, natural fabrics, authentic art/vintage design, full kitchen, rain shower, stone patio, grill.

The Cabin - Ski House near Windham
The Cabin is set back, secluded, unbelievably cozy and wonderfully romantic. It's a place to reconnect and recharge, to listen to the river and hear the wind through the trees and indulge in slow lunches and long walks and truly marvel at the Catskills. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.

Private cabin - 7 mins from ski mountain
This is a 2 bedroom 1 bath house located just 7 minutes from the Windham ski mountain. The house is surrounded by scenic land with few neighbors to be seen. Skiing, fall foliage, swimming holes, hiking, golf, antiquing, horseback riding, local farms are just a few things to name that this area has to offer. The house itself is a true retreat, you will leave totally re-charged - sweet air, bird chirping, star gazing, grilling, bong fire or simply enjoy a few days of not seeing another soul :)

Hideaway Windham/Hunter Fireplace, Snow & Skiing
Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

CozyCatskillChalet w/ Hot Tub (Catskill Mountains)
At face value, IG: @cozycatskillchalet appears to be just a humble little getaway tucked in the Catksill Mountains of Windham, NY. But even the most discerning guests will be quickly spirited away by the rustic charm and postcard-eqsue surroundings all around. At night, can't-be-beat stargazing on the back deck (or while soaking in the hot tub) will have you convinced this humble hideaway is a lot more illustrious than it lets on. Disclaimer: The chalet is not a luxury hotel or property.

*Farmhouse Chic with Mountain and Lake Views*
Welcome to Bright Sparrow Farmhouse! Located on 8 acres of private land with greenery and a wetland lake, this home is the perfect spot to reconnect with nature and enjoy quality time with loved ones. Just mins from Windham and Hunter mountains. Enjoy skiing, hiking, biking, zip lining, water park, lakes, dining, and winery. Our home is a sustainable retreat, powered by solar energy and equipped with a backup battery system. This means you'll enjoy a comfortable and uninterrupted stay.

Modern House with Mountain View @Getawind
Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

Alpine Chalet on Spectacular Property
Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

Chalet with HotTub 5 min to Windham, 15 min Hunter
Cozy Chalet style house nestled in a quiet spot and 5 minutes to Windham Mountain and close to hiking trails 15 minutes to Hunter Mountain 40 minutes to Belleayre Mountain. Relax by the fireplace after skiing TV with Netflix, Amazon and Hulu. Confortable couch with a equipped kitchen With 3 bedrooms. This property has a beautiful yard. Fairly private yet close to everything. Supermarket and restaurants near by (5 min by car) 15 min. to Colgate Lake 25 min. to Kaaterskill Falls

Cozy Creekside Cabin | 5 Mins to Windham Mt!
Nestled in the hills of Windham NY, the Creekside Cabin is a hidden gem just under 2.5 hours from NYC. Ideal for families and small groups of friends, this cozy cabin features three bedrooms, one bathroom, a comfortable living room overlooking a tranquil creek, and a fully equipped kitchen with a wood-burning fireplace. Whether you're looking for a weekend escape or a longer retreat, the Creekside Cabin offers a peaceful and relaxing stay in a beautiful natural setting.

Creekside Couple's Retreat w/Hot tub, Sauna & More
Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

Contemporary Cabin in Catskill Mountains
Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.
Popular amenities for Windham vacation rentals
Other great vacation rentals in Windham

EAT, DRINK, PLAY ... and Relax in Windham

Catskills Cabin on 100 Wooded Acres, Private Lake

Walk to town | 2 Mins to Ski | Windham Mill House

The Catskill Equestrian Cabin

The Mad Brook House | Walk to Main St, Windham

The Ski Ranch – 5min from Windham Mountain

Glass Cabin | Private Hot Tub | Catskills Nature

Hunter Mtn Log Cabin w/ View
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $693 CAD | $722 CAD | $555 CAD | $416 CAD | $421 CAD | $449 CAD | $474 CAD | $498 CAD | $438 CAD | $485 CAD | $485 CAD | $647 CAD |
| Avg. temp | -4 °C | -3 °C | 2 °C | 9 °C | 15 °C | 20 °C | 23 °C | 22 °C | 18 °C | 11 °C | 5 °C | -1 °C |
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Windham?
Yes! Work meets play with ease at over 80 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in condo rentals in Windham?
Experience the best of Windham with our condo rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Windham?
Four-legged friends are welcome in Windham. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there Windham house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Windham, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Windham have self check-in?
Absolutely! We offer over 40 house rentals with self check-in in Windham. Enjoy a tailored experience with all the comforts you desire.
Do chalet rentals in Windham have wifi?
Absolutely! We offer over 10 chalet rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Windham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windham have a gym?
Absolutely! We offer over 10 house rentals with a gym in Windham. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Windham?
Windham has more than 80 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Cabin Rentals in Windham?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with a bbq area, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Windham

Total vacation rentals
Explore 180 vacation rentals in Windham

Nightly prices starting at
Windham vacation rentals start at $125 CAD per night before taxes and fees

Verified guest reviews
Over 6,500 verified reviews to help you choose

Family-friendly vacation rentals
160 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
170 of Windham vacation rentals include wifi access

Popular amenities for guests
Guests love Self check-in, Gym, and BBQ grill across Windham rentals

4.9 Average rating
Windham stays are highly rated by guests—averaging 4.9 out of 5!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- Resorts World Catskills
- Windham Mountain
- Howe Caverns
- Thacher State Park
- Glimmerglass State Park
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Plattekill Mountain
- Bash Bish Falls State Park
- Zoom Flume
- Taconic State Park
- Norman Rockwell Museum
- Opus 40
- June Farms
- Naumkeag
- Berkshire Botanical Garden
- Millbrook Vineyards & Winery
- Hancock Shaker Village
- Walkway Over the Hudson State Historic Park
- Poets' Walk Park




