Vacation Rentals & Timeshares in Windham

/ Home
/ Vacation Rentals
/ United States
/ New York
/ Catskill Region
/ Windham
Book with confidence.

Updating...

age 0-16
59 Results

Relevance

Price: low to high

Price: high to low

Reviews

Why am I receiving these results?

59 timeshares

Why am I receiving these results?

“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: Air conditioning

All filters match

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: Air conditioning

All filters match

Price per night from

$113

“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: Air conditioning

All filters match

Price per night from

$401

The Presidential Suite at Brie & Bordeaux

Windham apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Air conditioning

All filters match

Price per night from

$315

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: Air conditioning

All filters match

Price per night from

$115

Responds fast! avg. 53 minutes

Match: Air conditioning

All filters match

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: Air conditioning

All filters match

Price per night from

$915

Great rentals within 20 miles that match your search

Contemporary, Secluded Cabin In The Heart of Woodstock

Woodstock log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“A place to do everything, or nothing” I must confess, that I did not expect much, hearing from a local friend who drove by the property. While previous vacations advertised themselves as located in Woodstock, this one truly is. Took us an hour and fourty minutes from manhattan, door to door. While it looked a little quirky at first sight, with an extension above the living room, once we entered we realized that it serves as a giant sky light, opening the space to the surrounding woods. The living area is spacious,filled with light, while the adjacent bedroom is cozy and rather romantic. Out of the woods and just down the road is the 'sunfrost' market and deli where we had our best juice ever at lunch time. After an afternoon stroll in Woodstock we spent the evening on the deck with a glass of Pinot. A red tailed hawk joined us for a while perched on a branch above a neat pile of cut wood, but soon lost interest and flew away. With the wine in-tow we plunged into the hot tub the way of adam and Eve. The next day I mostly lazed around, while wify practiced her graceful Tai-Chi on the deck. we had a great dinner at the 'red onion' which can not be put to shame by any New York establishment triple it's price. In short; secluded, romantic and a perfect weekend escape.

Match: Air conditioning

All filters match

Price per night from

$287

Match: Air conditioning

All filters match

Price per night from

$567

Spectacular Ski Vacation House - Incredible Views!

Shandaken house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Air conditioning

All filters match

Price per night from

$458

Village Suites at Fleischmanns - Suite 1

Fleischmanns apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Air conditioning

All filters match

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: Air conditioning

All filters match

Price per night from

$189

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: Air conditioning

All filters match

Price per night from

$447

Stately Civil War House near Hunter Mountain Skiing

Palenville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Air conditioning

All filters match

Price per night from

$430

Windham Cabin

Lexington log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Air conditioning

All filters match

Price per night from

$172

Stunning Vacation Country & Ski House

Woodstock house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Air conditioning

All filters match

Price per night from

$630

Charming Artist's Cottage

Woodstock house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 5 minutes

Match: Air conditioning

All filters match

Price per night from

$229

Margaret's Cottage in Woodstock Village

Woodstock log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$189

Charming Converted Barn On 2+ Acres Walk To Town

Woodstock house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Air conditioning

All filters match

Price per night from

$487

Privacy & Luxury @ Heart of Woodstock w/ Hot Tub

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Air conditioning

All filters match

Price per night from

$327

Marigold cabin by the stream - Heart of Woodstock with Hot Tub & Fireplace

Woodstock cottage

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$304

Match: Air conditioning

All filters match

Price per night from

$687

Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski

Woodstock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Air conditioning

All filters match

Price per night from

$682

Village Suites at Fleischmanns - Suite 2

Fleischmanns hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Air conditioning

All filters match

Price per night from

$189

charming house in the catskills

Jewett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Air conditioning

All filters match

Price per night from

$287

Charming house in great location

Jewett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Air conditioning

All filters match

Price per night from

$287

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!

Match: Air conditioning

All filters match

Price per night from

$269

Charming Artists Cottage

Woodstock house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$229

Affordable Windham Getaway (near private creek!)

Ashland house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Match: Air conditioning

All filters match

Price per night from

$172

Daydream Mountain Art Chateau '73 | Catskill

Catskill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

Match: Air conditioning

All filters match

Price per night from

$687

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

Woodstock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$401

Romantic Country Barn By the Stream

Woodstock log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$281

Waterfalls and Swimming Holes

Palenville apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$247

Match: Air conditioning

All filters match

Price per night from

$401

The Country Place Resort Home of Zoom Flume Water park

East Durham hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Air conditioning

All filters match

Price per night from

$171

Chateau Tina Tiny Luxury Cabin Sleeps 6 Dog Friendly

East Durham guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Air conditioning

All filters match

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

Match: Air conditioning

All filters match

Price per night from

$292

Cozy Cabin Sleeps 2 Dog Friendly

East Durham guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Air conditioning

All filters match

Price per night from

$228

Viewing 38 of 59
rentals in Windham

×

Also consider