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Number of reviews
185 timeshares
Price per night from
$231
Price per night from
$460
Catskill Cottage Vacation Rental - Cozy Getaway by Windham and Hunter Mountain
Windham house
2 bedrooms / 1 bathroom / sleeps 6
“Home away from home” My sisters and I rented this cottage on Labor day weekend for our annual sisters get away. Ella was very helpful giving exact directions to the cabin which is important when you are not familiar with a location. She was able to suggest many activities in the area as well as cute little restaurants/taverns in towns nearby. The cabin was truly like a home away from home. Ella clearly takes pride in the upkeep of the property. You are within walking distance to a grocery store, café, liquor store and a little store where you can find many necessities. This is a great get away for any time of the year. I am hoping to return sometime in the next year!
Responds fast! avg. 1 hour 45 minutes
Price per night from
$115
Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham
Windham log cabin
1 bedroom / 1 bathroom / sleeps 2
“Best weekend ever :)” I have recently rented the bungalow and just have great things to say about it. The place is so cozy, and cute, they had everything we needed and the location couldn't be better. It's very close to any of the skii resorts and many attractions, market...It was only my boyfriend and I and the bungalow was just the perfect choice to spend a holiday weekend. Ella, the owner, was very helpful providing us any info we could need. We are already planning to go back the beggining of the year and summer for sure. Thank you so much Ella!!!
Responds fast! avg. 1 hour 45 minutes
Price per night from
$103
Price per night from
$458
The Mountain House: The Perfect 4 Season Retreat
Windham chalet
8 bedrooms / 7 bathrooms / sleeps 22
Price per night from
$2,857
***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***
Windham house
2 bedrooms / 2 bathrooms / sleeps 5
Responds fast! avg. 1 hour 55 minutes
Price per night from
$200
Price per night from
$572
“Beautiful! Relaxing! Perfect!” I spent 4th of July weekend with a group of friends at this wonderful mountain retreat, and it was all that we wished and more!! The views are spectacular, the private pond and the mountains added so much to our stay. It was like being on a private resort...the home had everything we needed to have fun and enjoy this long summer weekend, and we are already planning to return next year. Thank you so much for providing such an amazing spot for a long weekend getaway! And it must be noted how accommadating and easy it was to communicate with the owner and with flipkey whenever I had any questions-- 5 Stars!
Price per night from
$404
*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw
Windham house
4 bedrooms / 2 bathrooms / sleeps 8
“Terrific Rental in Windham” This is a great rental property. The house is very well maintained and comes complete with everything you need for your visit. This includes the kitchen where many other rental properties offer sparse and/or low quality utensils, plates, etc. Angel has literally thought of everything and organized the property to make your stay enjoyable. Also, the hot tub has very potent jets which was nice for a bunch of middle aged golfers after a long day on the course. Angel was extremely helpful and responsive throughout the entire rental process. If you are coming to Windham you will be hard pressed to find a nicer property.
Price per night from
$201
Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!
Windham tented camp
1 bedroom / 1 bathroom / sleeps 4
Responds fast! avg. 1 hour 45 minutes
Price per night from
$127
Price per night from
$253
Price per night from
$231
Catskill Getaway - Ideal for Skiers Windham and Hunter Mountain Vacation Rental
Windham apartment
1 bedroom / 1 bathroom / sleeps 3
Responds fast! avg. 1 hour 45 minutes
Price per night from
$102
Luxe Windham Home w/Hot Tub - Walk to Ski Resort!
Windham house
8 bedrooms / 3 bathrooms / sleeps 17
Responds fast! avg. 3 hours 17 minutes
Price per night from
$341
Responds fast! avg. 3 hours 17 minutes
Price per night from
$569
Responds fast! avg. 3 hours 17 minutes
Price per night from
$238
Responds fast! avg. 3 hours 17 minutes
Price per night from
$238
Tentrr Signature Site - Pleasant Valley Maplecroft Camp
Windham tented camp
1 bedroom / 1 bathroom / sleeps 6
Responds fast! avg. 3 hours 30 minutes
Price per night from
$144
Responds fast! avg. 3 hours 17 minutes
Price per night from
$161
Catskills House w/Yard, 1Mi to Windham Mtn Resort!
Windham house
6 bedrooms / 2 bathrooms / sleeps 10
Responds fast! avg. 3 hours 17 minutes
Price per night from
$242
Responds fast! avg. 3 hours 17 minutes
Price per night from
$368
NEW! Catskills Home: Ponds, Tennis + Movie Theater
Windham house
4 bedrooms / 5 bathrooms / sleeps 10
Responds fast! avg. 3 hours 17 minutes
Price per night from
$1,777
NEW! Stylish Mtn Escape w/ Hot Tub, 3 Miles to Ski
Windham house
3 bedrooms / 2 bathrooms / sleeps 8
Responds fast! avg. 3 hours 19 minutes
Price per night from
$297
Price per night from
$913
Responds fast! avg. 3 hours 17 minutes
Price per night from
$492
Modern & Cozy Windham Mountain Home: Hike & Tennis
Windham house
6 bedrooms / 4 bathrooms / sleeps 12
Responds fast! avg. 3 hours 17 minutes
Price per night from
$889
Responds fast! avg. 3 hours 17 minutes
Price per night from
$143
5 Min to Windham Mtn! Luxury Retreat w/Amazing Views! Natural Swimming Pond
Windham villa
8 bedrooms / 7 bathrooms / sleeps 22
Price per night from
$3,463
Great rentals within 20 miles that match your search
Spectacular Ski Vacation House - Incredible Views!
Shandaken house
4 bedrooms / 3 bathrooms / sleeps 10
Price per night from
$457
“Our second home!” Tumblin' Falls has been our home away from home since we first discovered it in the mid-1990s. There's no better place to kick back and enjoy the mountain air, the beautiful waterfall, the company of wonderful people, and the warm feeling of a small town. The house is beautifully nostalgic and comfortable, and it's located within range of destinations like the Windham ski area, and the Cobleskill caves, Secret Caverns and Howe Caverns. We love Linda and Hugh, who greet us with "welcome home" each time we arrive. There is no better place to leave your cares behind, and embrace the beauty of the Catskills!
Responds fast! avg. 3 hours 3 minutes
Price per night from
$799
Responds fast! avg. 2 hours 35 minutes
Price per night from
$742
3 BR Ski in Ski out Condo at The Hunter Highlands
Hunter apartment
3 bedrooms / 3 bathrooms / sleeps 9
Price per night from
$400
Windham Skiers Book Now! Cottage North Catskills
Greenville cottage
2 bedrooms / 1 bathroom / sleeps 7
Price per night from
$377
“Awesome getaway!” I came here with a group of friends for a getaway weekend, and it was awesome! The house is big and comfortable. Huge backyard where you can relax and nearby is a little river where you can walk to. The owners of the house are super friendly and always tried to make you feel comfortable. Definitely would recommend this to others and I would sure be coming back.
Price per night from
$297
Price per night from
$570
Charming Converted Barn On 2+ Acres Walk To Town
Woodstock house
5 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$485
Viewing 38 of 185
rentals in Windham
About Windham
Known to Native Americans as 'The Land in the Sky', Windham is perfect for the outdoor enthusiast. With nature and activities at the heart of the town, you'll have plenty to do and see. Book your Windham vacation rental with FlipKey today.
About Windham
Windham is a town located in Greene County and was first settled in around 1780. These days, locals gain their main source of income from the ski resort in the Windham mountains, which attracts tourists from the New York area three hours away. It features 54 trails and 12 lifts, with its highest peak at 3,100 feet.
If you fancy trekking around the rivers and streams, you'll be sure to find a large variety of fish and other wildlife, such as deer and turkeys.
What to do
As mentioned, Windham Mountain Resort is the main reason why tourists travel to this particular town in New York. With ninety-seven percent snow coverage, you'll have the best possible snow conditions to make the most of your trip. This activity would definitely be for thrill-seekers looking to add another cool activity to their bucket-list!
There's also an adventure park at Windham Mountain—another exciting experience for those looking for active pursuits. Here, you can have a go on a high zip-line, try off-road go-karting, trampolines and even test your skills at a skate park.
You may even decide to take a trip to Windham Golf Club where you can play on an 18-hole golf course. This charming course in the picturesque Catskills was designed in 1928.
While there's plenty to keep outdoors enthusiasts occupied, there's also the option to completely chill-out. The town is filled with relaxing spas which offer several treatments, so you can feel fully refreshed after a tiring day.
Top travel tips
To get around Windham, use a car—there are no major public transport. This is especially relevant if you wish to go to the Windham Mountain due to the remoteness of the area.
There are bike rentals you can hire for your vacation, which is perfect if you wish to explore more of the area.
The weather in Windham is fairly cool all year round, which is to be expected of a snow resort! In the months of January and February, temperatures can reach lows of -1 degree Fahrenheit.
Take a trip to Windham this year for an outdoor adventure you'll never forget. Packed with active pursuits and relaxing scenic views, this small town is definitely worth the visit. Book your Windham rental with FlipKey and experience it for yourself.
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