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Vacation Rentals & Timeshares in Windham

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227 timeshares

Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham

Windham log cabin

1 bedroom / 1 bathroom / sleeps 2

“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. 2 hours 1 minutes

Price per night from

$81

A Stunning Upstate NY Property

Windham house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$889

“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. 1 hour 41 minutes

Price per night from

$87

Two-Story, 3-Bedroom Family Home

Windham house

3 bedrooms / 1 bathroom / sleeps 4

Price per night from

$237

Secluded Charming Water Front Log Home

Windham house

4 bedrooms / 2 bathrooms / sleeps 15

Price per night from

$438

Brand new 4-bedroom ski chalet with bucolic mountain, lake and meadow views.

Windham house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$633

Windham Mountain Ski House with Great Views

Windham house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$415

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

$345

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

Windham house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 22 minutes

Price per night from

$208

The Mountain House: The Perfect 4 Season Retreat

Windham chalet

8 bedrooms / 7 bathrooms / sleeps 22

Price per night from

$2,961

*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw

Windham house

4 bedrooms / 2 bathrooms / sleeps 8

“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.

Responds fast! avg. 28 minutes

Price per night from

$203

Windham Mountain Ski House

Windham house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$593

Chickadee Chalet

Windham apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$415

Country Convenient 2, 2bd townhouse Windham Hunter

Windham townhouse

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 36 minutes

Price per night from

$98

Beautiful apartment with great views!

Windham apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$237

The Presidential Suite at Brie & Bordeaux

Windham apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$504

The Xenia

Windham house

4 bedrooms / 3 bathrooms / sleeps 16

Responds fast! avg. 1 hour 17 minutes

Price per night from

$593

Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!

Windham tented camp

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 1 minutes

Price per night from

$103

WINDHAM MAGNIFICENT HOLIDAY GETAWAY

Windham house

5 bedrooms / 4 bathrooms / sleeps 18

Responds fast! avg. 2 hours 53 minutes

Price per night from

$1,065

Mountain Treasure Cottage, WIndham, NY

Windham cottage

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$295

Cristal pound at Windham ski resort

Windham condo

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$237

Responds fast! avg. 2 hours 1 minutes

Price per night from

$81

Restored Firehouse w/Theater 1mi to Windham Mtn!

Windham townhouse

4 bedrooms / 2 bathrooms / sleeps 16

Responds fast! avg. 4 minutes

Price per night from

$1,067

NEW-Spacious Home 2Mi to Windham Mountain & Resort

Windham house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 4 minutes

Price per night from

$309

NEW! Condo w/Loft: 2 Miles to Windham Mountain Ski

Windham condo

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$161

Spacious House - 1 Mi. to Windham Ski Resort!

Windham house

5 bedrooms / 2 bathrooms / sleeps 13

Responds fast! avg. 4 minutes

Price per night from

$236

Tentrr Signature - Pleasant Valley Maplecroft Camp

Windham tented camp

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$127

'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!

Windham house

12 bedrooms / 10 bathrooms / sleeps 33

Responds fast! avg. 4 minutes

Price per night from

$2,371

Luxe Windham Home w/Hot Tub - Walk to Ski Resort!

Windham house

8 bedrooms / 3 bathrooms / sleeps 23

Responds fast! avg. 4 minutes

Price per night from

$342

Catskills House w/Yard, 1Mi to Windham Mtn Resort!

Windham house

6 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 4 minutes

Price per night from

$242

NEW! Cozy Condo: Hike & Ski the Catskill Mountains

Windham condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 4 minutes

Price per night from

$161

Modern Home w/ Deck, 5 Minutes to Windham Resort!

Windham house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 4 minutes

Price per night from

$150

Amazing 4 BR on Windham

Windham villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$326

'The Mountain House' Windham Retreat w/ Hot Tub!

Windham house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 4 minutes

Price per night from

$410

Great rentals within 20 miles that match your search

Historic Catskill Mountain House close to Windham

Durham house

7 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$771

Phoenicia Hideaway - Your second home in the Catskills

Phoenicia house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$187

Belleayre Cozy Cabin

Fleischmanns log cabin

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 50 minutes

Price per night from

$148

Modern Ski Chalet at the base of Hunter Mountain

Hunter house

7 bedrooms / 3 bathrooms / sleeps 16

Price per night from

$473

Viewing 38 of 227
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

Country Convenient 2, 2bd townhouse Windham Hunter
Fall in the Catskills!!

We stayed four months. This is an apartment complex with one of the six units being a vacation rental. A very good place to stay, with everything we needed!! Had a great kitchen, good AC and heat, lovely view (great sunsets) out the back sliders, comfortable couches, and good internet connection. … see more
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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