Vacation Rentals & Timeshares in Windham

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40 timeshares

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“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. 53 minutes

Match: Horse riding

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Price per night from

$102

“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. 53 minutes

Match: Horse riding

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Price per night from

$113

Two-Story, 3-Bedroom Family Home

Windham house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

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!

Match: Horse riding

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Price per night from

$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

$401

Chickadee Chalet

Windham apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$401

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

Windham tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 53 minutes

Match: Horse riding

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Price per night from

$115

Cristal pound at Windham ski resort

Windham condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$229

Responds fast! avg. 53 minutes

Match: Horse riding

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Price per night from

$107

On Windham Mountain - Westside Chalet

Windham chalet

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Responds fast! avg. 1 hour 40 minutes

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Price per night from

$915

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Price per night from

$3,435

Great rentals within 20 miles that match your search

Saugerties, Woodstock, Catskills, Hunter, HITS, Rental House

Saugerties house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Awesome Columbus Weekend” Myself and 4 friends stayed here for a long Columbus Day weekend. This place is just what we needed. We are all from NYC so the location was extermely convenient for us. The Catskills are just a short drive from the city...well worth the drive. The house was great. Very clean, spaceous, and accommodating. It is located very close to the town of Saugerties and close to Woodstock and Hunter Mtn. The owners are very helpful and generous. I highly recommend this house.

Match: Horse riding

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Price per night from

$247

Catskill Mountain View House, Belleayre, Fire Pit!

Roxbury house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

“Best house ever” The house is in a beautiful setting. So many things to do in the area from antique shopping, golf in the summer, winter skiing, hiking, really great restaurants. Once you've seen the house though, you won't want to leave. Great layout for families, group of friends, special occasions or just getting away to a special place. everything is provided for your stay. Fully equipped kitchen, comfortable beds, outdoor fire pit!!! Watch shooting stars at night. Jennifer has thought of everything. Even a playroom with toys and games! No preparation is needed on your part. Just show up for a fabulous stay.

Match: Horse riding

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Price per night from

$447

Stately Civil War House near Hunter Mountain Skiing

Palenville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$430

Catskill Home for Skiing, Fishing, Hiking & biking

Fleischmanns house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 22

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Price per night from

$573

Catskill Mountains Retreat for Large Groups

Big Indian villa

  • 20 bedrooms
  • 7 bathrooms
  • sleeps 32

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Price per night from

$1,390

Privacy & Luxury @ Heart of Woodstock w/ Hot Tub

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$327

charming house in the catskills

Jewett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$287

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.

Match: Horse riding

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Price per night from

$212

Hunter Mountain Ski House Condo Ski Season Rental

Hunter apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$115

Modern Converted Barn with Amazing Mountain Views

West Kill house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 10

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Price per night from

$401

T Lounge & Accomodations

Tannersville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$327

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

Fleischmanns farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Horse riding

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Price per night from

$115

Log House Near Ski Resorts with Sauna Hot Tub Fire Pit

Maplecrest house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Horse riding

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Price per night from

$487

45 Acre Private Catskills Villa with Private Pond and River

Jewett villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 22

Match: Horse riding

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Price per night from

$1,140

15 Acre Catskills Sanctuary with Private Lake, Nature Lovers Retreat

Jewett cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Horse riding

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Price per night from

$572

The Hartwood House - Upstate NY Getaway

Saugerties house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Horse riding

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Price per night from

$447

Luxury Catskill Villa 5 Bedrooms/3 Baths/Jacuzzi/Fire pit/Ski Hunter,Windham

Prattsville villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Horse riding

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Price per night from

$1,030

Tranquil Woodstock Home in the Woods with Hot Tub and Ping Pong

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$401

Waterfalls and Swimming Holes

Palenville apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$247

Gorgeous 4 Room Villa in Catskills

Acra villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$344

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

Hunter house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 15

Match: Horse riding

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Price per night from

$859

Charming Artist's Cottage

Woodstock house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 5 minutes

Match: Horse riding

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Price per night from

$229

Hunter Mt-REDUCED~Amazing Views-Big House! 5 min to SLOPES!

Hunter house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Great Owner to Work With” I didn't get to stay in the house because of schedule conflicts but I still would like to highly recommend the owner. I sent her inquiries about the place and she gave me instant response and she was willing to work with my budget and arrange so many nice things for me to enjoy the house. She is a very kind person to work with and she is so patient and understanding ( I had a large group to work with and each one of my friend had a different idea). I trusted her from the second she contacted me and would very much stay here in the near future.

Match: Horse riding

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Price per night from

$682

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Price per night from

$2,290

Ski Chalet with Mountain Views - Grill & Firepit

Prattsville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$533

Romantic Country Barn By the Stream

Woodstock log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Horse riding

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Price per night from

$281

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Price per night from

$567

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