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Vacation Rentals & Vacation Rentals in Windham

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Vacation Rentals & Vacation Rentals in Windham

About Windham

202 timeshares

“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

Responds fast! avg. 52 minutes

Price per night from

$75

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***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***

Windham house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 44 minutes

Price per night from

$225

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Mountain House Retreat-Catskill Mountains-Windham, NY:

Windham house

5 bedrooms / 2 bathrooms / sleeps 10

“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.

Price per night from

$300

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The Catskills Tranquility House

Windham house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$300

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Cristal pound at Windham ski resort

Windham condo

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 24 minutes

Price per night from

$200

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Secluded Charming Water Front Log Home

Windham house

4 bedrooms / 2 bathrooms / sleeps 15

Price per night from

$250

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*4SeasonNirvana*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 ut

Responds fast! avg. 24 minutes

Price per night from

$325

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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 man

Responds fast! avg. 52 minutes

Price per night from

$69

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Country Convenient 2, 2bd townhouse Windham Hunter

Windham townhouse

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 32 minutes

Price per night from

$85

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Two-Story, 3-Bedroom Family Home

Windham house

3 bedrooms / 1 bathroom / sleeps 4

Price per night from

$200

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Responds fast! avg. 52 minutes

Price per night from

$69

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Brand new 4-bedroom ski chalet with bucolic mountain, lake and meadow views.

Windham house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$550

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Chickadee Chalet

Windham apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 40 minutes

Price per night from

$350

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The Mountain House: The Perfect 4 Season Retreat

Windham chalet

8 bedrooms / 7 bathrooms / sleeps 22

Price per night from

$2,500

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Mountain Treasure Cottage, WIndham, NY

Windham cottage

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 15 minutes

Price per night from

$249

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Windham Mountain Ski House with Great Views

Windham house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$350

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The Presidential Suite at Brie & Bordeaux

Windham apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$425

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Amazing Mountain Views, Total Privacy

Windham house

4 bedrooms / 3 bathrooms / sleeps 13

Price per night from

$290

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Windham Mountain Ski House

Windham house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$500

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A Stunning Upstate NY Property

Windham house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$750

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2 Bedroom 2 Bath Condo, Sleeps 7. Just Minutes from Windham Ski Mountain.

Windham condo

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$225

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NEW! Catskills Area Loft-Style Condo in Downtown!

Windham studio

Studio / 2 bathrooms / sleeps 6

Responds fast! avg. 51 minutes

Price per night from

$125

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Beautiful apartment with great views!

Windham apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$199

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NEW! Cozy Windham Condo w/ Pool & Tennis Courts!

Windham apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 51 minutes

Price per night from

$110

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WINDHAM MAGNIFICENT HOLIDAY GETAWAY

Windham house

5 bedrooms / 4 bathrooms / sleeps 18

Responds fast! avg. 3 hours 38 minutes

Price per night from

$899

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Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!

Windham tented camp

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 52 minutes

Price per night from

$89

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Exclusive! 4 BR Windham, NY-262440

Windham villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 30 minutes

Price per night from

$420

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Ukroatian Mountain Kucha 4 beds, 2 baths, Sleeps 12

Windham house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$260

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Amazing 4 BR on Windham

Windham villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$250

1 / 39

The Xenia

Windham house

4 bedrooms / 3 bathrooms / sleeps 16

Price per night from

$500

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About Windham

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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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