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Vacation Homes in Windham

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

10.0 out of 10, Exceptional, (176)
"We loved our stay at this home! It is full of so much light and good vibes. We planned the weekend around a concert at Levon Helms studio, which was right down the street. The owners/management were wonderful & easy to get in touch with (not that we needed anything). The deck & music room were enjoyed the most :)"
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

10.0 out of 10, Exceptional, (39)
"Absolutely loved the property and its proximity to the Bearsville Theatre where we had a 2-day concert. We only wish we could have stayed longer than a quick weekend trip!"
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

Beautiful, private Property/swimming pond

9.6 out of 10, Exceptional, (71)
"We had an amazing stay at this home during our family ski trip. The house was spacious, clean, and perfectly located near the slopes. The host was responsive and made sure we had everything we needed. We would definitely stay here again—highly recommend for a relaxing and fun ski getaway."
Beautiful, private Property/swimming pond

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

9.0 out of 10, Wonderful, (48)
"Great communication with host Nice spacious clean apartment. Good location "
The price is AED 430
AED 758 total
includes taxes & fees
20 Jul - 21 Jul
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

A world where time stands still, close to Belleayre Ski & Wedding venues.

9.6 out of 10, Exceptional, (17)
"Had a great "
The price is AED 975
AED 2,362 total
includes taxes & fees
19 Jul - 20 Jul
A world where time stands still, close to Belleayre Ski & Wedding venues.

The Catskills Red Barn-near Belleayre

10.0 out of 10, Exceptional, (45)
"Blythe is super helpful. We had a fantastic night in the cabin, which had so much character. Belleayre is so close, it’s a great little getaway to go and have some fun. "
The Catskills Red Barn-near Belleayre

Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

9.8 out of 10, Exceptional, (74)
"Very relaxing, well equipped home. Hot tub was fantastic. Kitchen fully stocked with pots, pans, cooking and eating utensils. "
Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace

10.0 out of 10, Exceptional, (41)
"Excellent log cabin home, perfect home base for a ski weekend at Windham. "
Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace

Cozy Chic Bungalow with Fireplace, Sauna, Fast WiFi in Quaint Phoenicia

2.0 star property
8.8 out of 10, Excellent, (17)
"Really nice home with great interior style and fully functional kitchen in a great town in the heart of the Catskills. Definitely want to come back!"
The price is AED 551
AED 1,242 total
includes taxes & fees
3 Aug - 4 Aug
Cozy Chic Bungalow with Fireplace, Sauna, Fast WiFi in Quaint Phoenicia

Charming Catskill getaway walking distance to Main St. Pet-friendly!

10.0 out of 10, Exceptional, (3)
"We had a great stay here! The check in process was super easy and Jiyon was very communicative. The house was super comfortable and conveniently located for a weekend of hiking. Would definitely stay here again!"
Charming Catskill getaway walking distance to Main St. Pet-friendly!

<br>Escape to our incredibly private home on 30 acres!

10.0 out of 10, Exceptional, (136)
"If you’re looking for a quiet, hidden retreat with endless things to do, this is your spot! Such a gem tucked away into the woods. "
<br>Escape to our incredibly private home on 30 acres!

Peaceful River Retreat with Fireplace & Panoramic Views

10.0 out of 10, Exceptional, (11)
"Very nice location, beautiful views of the Hudson river . Modern house, clean and good amenities. Owner was responsive to any question we had. We really enjoyed our stay, would highly recommend. "
Peaceful River Retreat with Fireplace & Panoramic Views

Blackbear Lodge - Luxury Cabin, Kid-Friendly

10.0 out of 10, Exceptional, (4)
"We had a great stay here! Everything was comfortable and just all around easy. The location is amazing—we loved that it's tucked away and private without being so out of the way. "
Blackbear Lodge - Luxury Cabin, Kid-Friendly

StarryPinesCottage w Salt Hot Tub & Cedar Sauna Mins to Slopes

9.8 out of 10, Exceptional, (13)
"We came up here for an extended weekend getaway and couldn’t have chosen a better place to stay. The location really is 15 minutes away from everything! From skiing to restaurants and bars you can find everything just a short drive away. And while you stay at the property, the amenities are awesome and everything is clean and works well! The hosts are incredibly kind and I can’t say enough about how much we enjoyed our stay. "
StarryPinesCottage w Salt Hot Tub & Cedar Sauna Mins to Slopes

Cozy Waterfall Home | Close to All Mountains/Hikes

3.0 star property
10.0 out of 10, Exceptional, (3)
"The host is very responsive and the listing is accurate about what to expect with the property."
The price is AED 397
AED 1,059 total
includes taxes & fees
21 Jul - 22 Jul
Cozy Waterfall Home | Close to All Mountains/Hikes

Your peaceful, private retreat, escape with friends & family! Incredible views!

10.0 out of 10, Exceptional, (37)
"We had a great time at the house , it sits on a hill with great views of the Catskills. Even though it was very cold outside we were very comfortable in the house. Three fireplaces and a hot tub made it warm and cozy."
Your peaceful, private retreat, escape with friends & family! Incredible views!

Come and stay at our Catskill Hideaway!<br>Freehold, NY

10.0 out of 10, Exceptional, (17)
"Great Stay. Just what we needed and just as described."
Come and stay at our Catskill Hideaway!<br>Freehold, NY

Family Home w/ Yard & Fire Pit in Middleburgh!

9.4 out of 10, Exceptional, (3)
"Really beautifully situated house for enjoying the Catskills. Plenty of room for a family. Lots of cozy nooks. Had a great time trying out the nearby diners. "
Family Home w/ Yard & Fire Pit in Middleburgh!

Cozy year round retreat! Close to skiing, hiking and swimming.

10.0 out of 10, Exceptional, (43)
"Summer in the Catskills is a treat and these are the accommodations to enjoy it to its fullest. Can’t wait to stay again!"
Cozy year round retreat! Close to skiing, hiking and swimming.

Hunter Mountain Home w/ Game Room: 1 Mi to Skiing!

9.4 out of 10, Exceptional, (6)
"The cabin is perfect…cozy yet sleeps 13, clean, nice decor, minutes to Hunter Mtn, and lots games to entertain the teens (pool, ping pong, darts, shuffle board, etc)! Would definitely recommend this property! "
Hunter Mountain Home w/ Game Room: 1 Mi to Skiing!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windham Hotel Reviews