Ashland Rentals

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Affordable Windham Getaway (near private creek!)

Ashland house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

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Price per night from

$173

Great rentals within 20 miles that match your search

Catskill Victorian Fireplaces/ Hot Tub sleeps 12

Margaretville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$517

Spectacular Ski Vacation House - Incredible Views!

Shandaken house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$459

Village Suites at Fleischmanns - Suite 1

Fleischmanns apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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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.

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Price per night from

$190

Margaretville, Great Vewsi, AC, Fast Internet, near Roxbury Wedding Venues

Margaretville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Wonderful view” Very clean and provided with everything. The view from the hill was amazing. I Enjoyed my stay and would definitely return. Lots to do in the area including some very good restaurants.

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Price per night from

$183

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.

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Price per night from

$448

Windham Cabin

Lexington log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$173

“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

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Price per night from

$113

“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

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$103

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Price per night from

$689

Village Suites at Fleischmanns - Suite 2

Fleischmanns hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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Price per night from

$190

Responds fast! avg. 53 minutes

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Price per night from

$107

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

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$115

Romantic Country Barn By the Stream

Woodstock log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$282

Second Wind

Hobart apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$144

The Country Place Resort Home of Zoom Flume Water park

East Durham hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$171

Chateau Tina Tiny Luxury Cabin Sleeps 6 Dog Friendly

East Durham guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$373

VILLA MARIE Luxury Cabin from our Tiny Cabin Collection Dogs ok

East Durham guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$293

Cozy Cabin Sleeps 2 Dog Friendly

East Durham guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$229

T Lounge & Accomodations

Tannersville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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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

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Price per night from

$402

Renovated Cozy Catskills Getaway!

Fleischmanns house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$197

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

$917

Mountain Top Home in Hunter

Hunter house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

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Price per night from

$517

HideAway Tiny Cabin Dog friendly Sleeps 5

East Durham house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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Price per night from

$339

Mountain View Tiny Cabin

East Durham cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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$459

Chalet in the town of Windham

Maplecrest house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$287

4 seasons mountain condo

East Jewett condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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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

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$488

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$919

Fleischmanns Streamside Retreat

Fleischmanns apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$183

Waterfalls and Swimming Holes

Palenville apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$247

Catskill Mountain Getaway

West Kill house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$373

“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

Stunning Vacation Country & Ski House

Woodstock house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

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$632

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$345

charming house in the catskills

Jewett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$287

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