Vacation Rentals & Timeshares in Windham

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54 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: Walking trips

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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: Walking trips

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Price per night from

$113

Windham Mountain Ski House with Great Views

Windham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Walking trips

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Price per night from

$574

“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: Walking trips

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Price per night from

$401

Chickadee Chalet

Windham apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Walking trips

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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: Walking trips

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Price per night from

$115

Responds fast! avg. 53 minutes

Match: Walking trips

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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

Match: Walking trips

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Price per night from

$917

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Price per night from

$3,442

Great rentals within 20 miles that match your search

Village Suites at Fleischmanns - Suite 1

Fleischmanns apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Walking trips

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Price per night from

$155

The Cottage at Chichester

Chichester cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

“Nice place to get away from the hectic city.” Quiet and secluded it was a good fit for me, a couple, their toddler and two small dogs. Property its a good size for a small walk in the woods. Storms have pushed the creek away from the back of the house and it's small and not showing any fish, so wasn't able to fish on the property. I'd advise getting your fishing license before you get there. The house was clean and well kept. The frig had a fair amount of condiments in them, so check the frig before you head to town to buy anything. There were enough pots and pans to cook, but we were glad we brought two cooking knives with us. The gas grill on the deck was OUTSTANDING! I give that grill 5 stars. Quiet with a great view of the stars. We took advantage of the fire pit and picnicked while cooking hot dogs over the open fire. The wifi was intermittent, which can be a good thing if you're looking to truly get away and relax.

Match: Walking trips

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Price per night from

$190

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: Walking trips

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Price per night from

$448

Pet Friendly Cabin Doh-Ray Up At 1450ft

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Relaxing mountain retreat” We enjoyed a very pleasant Thanksgiving week getaway at the cabin, which looks just like the pictures -- nice combination of modern and rustic design. Also very comfortable, clean and well organized. Tv and sound system very high tech. Somehow we did something wrong with the remotes and lost the tv connection, but Raymond was extremely patient troubleshooting over the phone. Kitchen is nicely equipped. Bathrooms, full upstairs and half downstairs (not pictured), were standard but fine. The views of the woods from the many windows were really pretty, especially in the snow. It was a bit of an adventure driving up the somewhat steep mountain road. Definitely need 4wd in bad weather, so car rental was a little expensive. Overall, we had a lovely stay and hope to have a chance to come back in the summer.

Match: Walking trips

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Price per night from

$362

Catskill Home for Skiing, Fishing, Hiking & biking

Fleischmanns house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 22

Match: Walking trips

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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: Walking trips

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Price per night from

$1,393

Village Suites at Fleischmanns - Suite 2

Fleischmanns hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Walking trips

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Price per night from

$190

Top of the Pass. Cozy Craftsman Style

Hunter house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$201

four season vacation rental

Tannersville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Match: Walking trips

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Price per night from

$115

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

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips

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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: Walking trips

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Price per night from

$281

T Lounge & Accomodations

Tannersville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Walking trips

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Price per night from

$327

Modern Converted Barn with Amazing Mountain Views

West Kill house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 10

Match: Walking trips

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Price per night from

$402

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

Fleischmanns farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Walking trips

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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

Match: Walking trips

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Price per night from

$1,142

15 Acre Catskills Sanctuary with Private Lake, Nature Lovers Retreat

Jewett cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Walking trips

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Price per night from

$573

4 seasons mountain condo

East Jewett condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Walking trips

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Price per night from

$517

Log House Near Ski Resorts with Sauna Hot Tub Fire Pit

Maplecrest house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Walking trips

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Price per night from

$488

The Hartwood House - Upstate NY Getaway

Saugerties house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Walking trips

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Price per night from

$448

New! Catskills Mountain Cozy 2 BED Cabin Getaway.

Prattsville chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$184

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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: Walking trips

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Price per night from

$1,032

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.

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Price per night from

$247

Charming house in great location

Jewett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$287

Catskill Mountain Getaway

West Kill house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Walking trips

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Price per night from

$372

Relaxed, Refined enchanting Cabin Retreat

Fleischmanns house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$211

Privacy & Luxury @ Heart of Woodstock w/ Hot Tub

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Walking trips

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Price per night from

$327

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

Woodstock log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Walking trips

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Price per night from

$298

Match: Walking trips

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Price per night from

$2,289

Viewing 38 of 54
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