Vacation Rentals & Timeshares in Windham

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27 timeshares

Mountain House Retreat

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. 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!

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$287

“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.

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Price per night from

$402

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Price per night from

$3,443

Great rentals within 20 miles that match your search

Charming Converted Barn On 2+ Acres Walk To Town

Woodstock house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

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$488

Catskill Home for Skiing, Fishing, Hiking & biking

Fleischmanns house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 22

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$574

Expanded Cabin facing Hunter Mountain in NY

Hunter log cabin

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

“Love it--would return again!” Jeffrey was very friendly, accommodating, helpful and professional as we were booking the cabin. Cabin was beautifully furnished and large enough to fit 8 of us. 5 min drive to Hunter Mountain. Very cozy and comfortable--loved it and would love to return again sometime in the future!

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Price per night from

$689

Catgalu, privacy and swimming pond

Arkville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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$322

Top of the Pass. Cozy Craftsman Style

Hunter house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$201

Mountain Top Retreat, 116 private acres

Hobart house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“The most peaceful vacation I have ever had!” The house is totally secluded and very pretty on the inside. All we needed to bring with us were clothes and food, the house had everything else we could have needed and a lot more. We brought our three children and they loved it. We spent most of our time at the swimming pond and around the fire at night.

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$213

Catskills Comfrey Farm - It's another beautiful day in the Catskills!

Fleischmanns farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$115

45 Acre Private Catskills Villa with Private Pond and River

Jewett villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 22

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$1,142

15 Acre Catskills Sanctuary with Private Lake, Nature Lovers Retreat

Jewett cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$573

4 seasons mountain condo

East Jewett condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$517

The Hartwood House - Upstate NY Getaway

Saugerties house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$448

Relaxed, Refined enchanting Cabin Retreat

Fleischmanns house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$212

NEW Modern Catskills Cabin w/ HOT TUB & views

Denver cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$517

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$2,296

Affordable Windham Getaway (near private creek!)

Ashland house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

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Price per night from

$173

Walk to Hunter Mountain

Hunter house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$173

charming house in the catskills

Jewett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$287

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$568

Family Friendly ~ Minutes to Hunter ~ Wooded Seclusion

Tannersville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$574

NYC ESCAPE-4 ACRES- WORK FROM HOME-SPECIAL SALE

Hunter house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 15

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$861

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$402

Stately Civil War House near Hunter Mountain Skiing

Palenville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$430

Sanctuary by the Stream

Phoenicia house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“A Little Taste of The Country” The property was exactly as described. When we did arrive John was available to "check us" into the house and show us some of the features. Veronica and John have paid close attention to every detail. A group of four of use stayed in June to attend the Taste of Country Music Festival at Hunter Mountain. The drive to the mountain was very accessible. Since we up there for the weekend for the festival, we did not have much time to explore the surrounding area. We did have dinner at SPORTSMAN’S ALAMO CANTINA right on main street. Great Mexican food and huge portions. It was a nice weekend away and the hospitality was impeccable!

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Price per night from

$269

Peaceful Getaway Cottage

Freehold house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$344

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