Vacation Rentals & Timeshares in Windham

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120 timeshares

“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

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

Price per night from

$113

Two-Story, 3-Bedroom Family Home

Windham house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$230

Windham Mountain Ski House with Great Views

Windham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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!

Price per night from

$287

***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***

Windham house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$201

“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.

Price per night from

$402

Windham Mountain Ski House

Windham house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$574

Chickadee Chalet

Windham apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$402

The Presidential Suite at Brie & Bordeaux

Windham apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$316

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

Price per night from

$131

Cristal pound at Windham ski resort

Windham condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$230

Responds fast! avg. 53 minutes

Price per night from

$107

On Windham Mountain - Westside Chalet

Windham chalet

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Responds fast! avg. 1 hour 1 minutes

Price per night from

$917

Price per night from

$3,442

Great rentals within 20 miles that match your search

Hunter Mountain Ski House Condo Ski Season Rental

Hunter apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$115

COZY STREAMSIDE SEASONAL COTTAGE NEAR SKI CENTER

Pine Hill house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$76

Charming Artists Cottage

Woodstock house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$230

A Stunning Upstate New York Property.

Westerlo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,090

charming house in the catskills

Jewett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$287

Charming house in great location

Jewett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$287

Top of the Pass. Cozy Craftsman Style

Hunter house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

Price per night from

$201

Cozy Log Cabin

Durham log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

Price per night from

$236

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.

Price per night from

$213

U have to C it 2 believe it ! unlike any other !

Haines Falls house

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 25

Price per night from

$1,147

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.

Price per night from

$287

Spectacular Ski Vacation House - Incredible Views!

Shandaken house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 20 minutes

Price per night from

$459

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.

Price per night from

$207

Historic Catskill Mountain House close to Windham

Durham house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$746

Cozy Cottage

Hunter cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 9 minutes

Price per night from

$230

Village Suites at Fleischmanns - Suite 1

Fleischmanns apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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.

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.

Price per night from

$448

Windham Skiers Book Now! Cottage North Catskills

Greenville cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Price per night from

$379

Everyday is a Holiday at this Vacation home

Fleischmanns house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$343

LAKE FRONT NYC DESIGNER Cabin - CATSKILLS, NY.

Stamford log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$459

Windham Cabin

Lexington log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$172

West Kill Retreat

West Kill house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

“Awesome getaway!” I came here with a group of friends for a getaway weekend, and it was awesome! The house is big and comfortable. Huge backyard where you can relax and nearby is a little river where you can walk to. The owners of the house are super friendly and always tried to make you feel comfortable. Definitely would recommend this to others and I would sure be coming back.

Price per night from

$299

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rentals in Windham

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About Windham

Known to Native Americans as 'The Land in the Sky', Windham is perfect for the outdoor enthusiast. With nature and activities at the heart of the town, you'll have plenty to do and see. Book your Windham vacation rental with FlipKey today.

About Windham

Windham is a town located in Greene County and was first settled in around 1780. These days, locals gain their main source of income from the ski resort in the Windham mountains, which attracts tourists from the New York area three hours away. It features 54 trails and 12 lifts, with its highest peak at 3,100 feet.

If you fancy trekking around the rivers and streams, you'll be sure to find a large variety of fish and other wildlife, such as deer and turkeys.

What to do

As mentioned, Windham Mountain Resort is the main reason why tourists travel to this particular town in New York. With ninety-seven percent snow coverage, you'll have the best possible snow conditions to make the most of your trip. This activity would definitely be for thrill-seekers looking to add another cool activity to their bucket-list!

There's also an adventure park at Windham Mountain—another exciting experience for those looking for active pursuits. Here, you can have a go on a high zip-line, try off-road go-karting, trampolines and even test your skills at a skate park.

You may even decide to take a trip to Windham Golf Club where you can play on an 18-hole golf course. This charming course in the picturesque Catskills was designed in 1928.

While there's plenty to keep outdoors enthusiasts occupied, there's also the option to completely chill-out. The town is filled with relaxing spas which offer several treatments, so you can feel fully refreshed after a tiring day.

Top travel tips

To get around Windham, use a car—there are no major public transport. This is especially relevant if you wish to go to the Windham Mountain due to the remoteness of the area.

There are bike rentals you can hire for your vacation, which is perfect if you wish to explore more of the area.

The weather in Windham is fairly cool all year round, which is to be expected of a snow resort! In the months of January and February, temperatures can reach lows of -1 degree Fahrenheit.

Take a trip to Windham this year for an outdoor adventure you'll never forget. Packed with active pursuits and relaxing scenic views, this small town is definitely worth the visit. Book your Windham rental with FlipKey and experience it for yourself.

Top Destination reviews

Catskill Cottage Vacation Rental - Cozy Getaway by Windham and Hunter Mountain
Perfect

We loved staying here. The cottage was absolutely sparking clean, easy to find and more than enough room for everything we needed. We were able to relax and spend a few days in the country for some hiking and much needed rest time and a good part of the reason we were immediately able to relax was the cottage. The beds were comfortable, the bathrooms were clean and with a microwave, TV, DVD player, etc. it was more like we were staying with a friend at their place than a rental.see more
Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham
Amazing weekend getaway

Thank you so much me and my girlfriend had an amazing weekend there it really was a great time. The cabin is so beautiful and so comfortable and I. A great area we can't wait to be back soon thanks again !! … see more
Mountain House Retreat
natural beauty and attention to detail

The following is an excerpt from an e-mail sent to the proprietor and the assistant/property manager to inform them of our complete satisfaction-just beautiful! We loved it so much we returned! "In addition to the beauty and tranquility of the property, we also have made note of the way in which both yourself and Kip treat your "house guests"-just simple things such as firewood, kitchen facilities, paper products etc. and asking if we are in need of anything shows your attention to detail. Again, our sincere gratitude and we are looking forward to the lovely weeks ahead at the mountain retreat!" Thank you Lynn and Kip for continuing to always make our stay a lovely one! The Roches 10/17/2013see more
*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw
Amazing mountain spot

We went to Chalet Montreuil for the weekend in summer and it was the best idea ever! The chalet is fully equipped and instructions couldn't be clearer. We spent 2 nights, we were 6 girls, and we enjoyed the BBQ, the kitchen and the amazing garden. Peaceful and quiet, the chalet is perfectly located - they are many activities to do around. We did hiking and paddling! Going back for sure!see more

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