Vacation Rentals & Timeshares in Windham

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50 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: Golf within 30mins drive

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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: Golf within 30mins drive

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Price per night from

$113

Two-Story, 3-Bedroom Family Home

Windham house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$230

Windham Mountain Ski House with Great Views

Windham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$574

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: Golf within 30mins drive

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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.

Match: Golf within 30mins drive

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Price per night from

$401

Chickadee Chalet

Windham apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$402

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: Golf within 30mins drive

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Price per night from

$115

Responds fast! avg. 53 minutes

Match: Golf within 30mins drive

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Price per night from

$107

Match: Golf within 30mins drive

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Price per night from

$3,440

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: Golf within 30mins drive

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Price per night from

$247

Village Suites at Fleischmanns - Suite 1

Fleischmanns apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Golf within 30mins drive

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Price per night from

$155

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: Golf within 30mins drive

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Price per night from

$448

Catskill Home for Skiing, Fishing, Hiking & biking

Fleischmanns house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 22

Match: Golf within 30mins drive

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Price per night from

$574

Catskill Mountains Retreat for Large Groups

Big Indian villa

  • 20 bedrooms
  • 7 bathrooms
  • sleeps 32

Match: Golf within 30mins drive

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Price per night from

$1,392

Privacy & Luxury @ Heart of Woodstock w/ Hot Tub

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$327

Catgalu, privacy and swimming pond

Arkville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Golf within 30mins drive

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Price per night from

$321

Village Suites at Fleischmanns - Suite 2

Fleischmanns hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Golf within 30mins drive

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Price per night from

$190

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: Golf within 30mins drive

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Price per night from

$213

A Peaceful Escape

Leeds house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 42 minutes

Match: Golf within 30mins drive

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Price per night from

$109

four season vacation rental

Tannersville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$115

Hunter Mountain Ski House Condo Ski Season Rental

Hunter apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Golf within 30mins drive

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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

Match: Golf within 30mins drive

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Price per night from

$402

T Lounge & Accomodations

Tannersville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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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: Golf within 30mins drive

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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: Golf within 30mins drive

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Price per night from

$488

Hunter Haven 2bdrm condo with Sauna

Hunter condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$229

45 Acre Private Catskills Villa with Private Pond and River

Jewett villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 22

Match: Golf within 30mins drive

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Price per night from

$1,141

15 Acre Catskills Sanctuary with Private Lake, Nature Lovers Retreat

Jewett cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Golf within 30mins drive

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Price per night from

$573

The Hartwood House - Upstate NY Getaway

Saugerties house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Golf within 30mins drive

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Price per night from

$448

Match: Golf within 30mins drive

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Price per night from

$299

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

Prattsville villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Golf within 30mins drive

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Price per night from

$1,031

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

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$402

Romantic Country Barn By the Stream

Woodstock log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$281

2 BR Cabin, Hot Tub, Fireplace, Heart of Woodstock

Woodstock log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$298

Match: Golf within 30mins drive

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Price per night from

$2,290

Charming Artist's Cottage

Woodstock house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 5 minutes

Match: Golf within 30mins drive

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Price per night from

$229

NEW Modern Catskills Cabin w/ HOT TUB & views

Denver cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$516

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