Vacation Rentals & Timeshares in Windham

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124 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. 1 hour 2 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. 1 hour 2 minutes

Price per night from

$114

Two-Story, 3-Bedroom Family Home

Windham house

3 bedrooms / 1 bathroom / sleeps 4

Price per night from

$229

Windham Mountain Ski House with Great Views

Windham house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$458

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

$401

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

Windham house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$201

*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.

Price per night from

$201

Windham Mountain Ski House

Windham house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$572

Chickadee Chalet

Windham apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$401

The Presidential Suite at Brie & Bordeaux

Windham apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$252

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

Windham tented camp

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 2 minutes

Price per night from

$131

Cristal pound at Windham ski resort

Windham condo

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 25 minutes

Price per night from

$229

Responds fast! avg. 1 hour 2 minutes

Price per night from

$103

Tentrr Signature Site - Pleasant Valley Maplecroft Camp

Windham tented camp

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 42 minutes

Price per night from

$101

On Windham Mountain - Westside Chalet

Windham chalet

6 bedrooms / 5 bathrooms / sleeps 14

Responds fast! avg. 2 hours 10 minutes

Price per night from

$914

5 Min to Windham Mtn! Luxury Retreat w/Amazing Views! Natural Swimming Pond

Windham villa

8 bedrooms / 7 bathrooms / sleeps 22

Price per night from

$3,432

Great rentals within 20 miles that match your search

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.

Responds fast! avg. 2 hours 58 minutes

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.

Price per night from

$446

Windham Skiers Book Now! Cottage North Catskills

Greenville cottage

2 bedrooms / 1 bathroom / sleeps 7

Price per night from

$378

Catskill Region Vacation Log Home Rental

Halcottsville house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$286

Catskill NY/ 2 Bedroom Cottage on Cauterskill Crk

Catskill cottage

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$258

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

$298

charming woodstock cottage with outdoor hottub

Willow cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$201

Catskills Belleayre House Rental

Fleischmanns house

5 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 45 minutes

Price per night from

$571

Charming Converted Barn On 2+ Acres Walk To Town

Woodstock house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$486

Catskill Mountains Retreat for Large Groups

Big Indian villa

20 bedrooms / 7 bathrooms / sleeps 32

Price per night from

$1,389

Price per night from

$687

Expanded Cabin facing Hunter Mountain in NY

Hunter log cabin

4 bedrooms / 2 bathrooms / sleeps 7

“Love it--would return again!” Jeffrey was very friendly, accommodating, helpful and professional as we were booking the cabin. Cabin was beautifully furnished and large enough to fit 8 of us. 5 min drive to Hunter Mountain. Very cozy and comfortable--loved it and would love to return again sometime in the future!

Responds fast! avg. 54 minutes

Price per night from

$687

Catgalu, privacy and swimming pond

Arkville house

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 2 hours 21 minutes

Price per night from

$332

Winter Rental For Upstate New York

Hunter apartment

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$134

Mountain Top Retreat, 116 private acres

Hobart house

2 bedrooms / 1 bathroom / sleeps 6

“Beautiful views, peaceful property” My husband and I wanted a change from our annual beach vacation and we were not dissapointed. The property is beautiful! So quiet and secluded, and the views were amazing! The ponds kept our 2 young boys occupied for hours and they loved building a fire in the pit every night. The pictures online do not do this property justice,us be seen in person to appreciate!

Responds fast! avg. 2 hours 22 minutes

Price per night from

$212

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

Haines Falls house

9 bedrooms / 9 bathrooms / sleeps 25

Price per night from

$1,144

charming house in the catskills

Jewett house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$286

Charming house in great location

Jewett house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$286

Log Home Lodging Rentals

Margaretville house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$308

Top of the Pass. Cozy Craftsman Style

Hunter house

4 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 24 minutes

Price per night from

$201

Cozy Log Cabin

Durham log cabin

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 21 minutes

Price per night from

$235

Viewing 38 of 124
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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