Holiday rentals in Windham

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Popular amenities for Windham holiday rentals

Stay near Windham's top sights

Chicken Run Family Restaurant and Steak House213 locals recommend
The Windham Local129 locals recommend
The Windham Path114 locals recommend
Millrock Restaurant105 locals recommend
Catskill Mountain Country Store - Windham105 locals recommend
Tap House Grille72 locals recommend

Other great holiday rentals in Windham

Guest favourite
Home in Windham
5 out of 5 average rating, 22 reviews

Cozy Mountain Cabin Near Windham Slopes

MardaRating, 5 stars2 weeks ago
Impressed by the attention to detail! Communication was seamless! The host was responsive and considerate, ensuring our stay was comfortable from start to finish The host stocked the kitchen with essentials. Highly recommend to anyone looking for a cozy and clean place to stay!
Top guest favourite
Home in Athens
5 out of 5 average rating, 38 reviews

Perfect home for a getaway from NYC

ScottRating, 5 stars1 month ago
Antonio and Yoon's place was perfect for our large group and dog. It's a very spacious home that is thoughtfully designed and in a lovely residential community. The beds and furniture were extremely comfortable, the backyard huge with a large patio and a fire pit. The six bedrooms, three full bathrooms, two living rooms, dining room, fully stocked kitchen, and finished basement gave our group of ten adults more than enough room to both gather together and enjoy time on our own. The location is near wonderful hikes and great restaurants and shops in Athens, Catskill, Hudson, and more. Antonio and Yoon were proactive, friendly, and clear in all communications. Highly recommended!
Guest favourite
Chalet in Hunter
4.98 out of 5 average rating, 153 reviews

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE

CarmenRating, 5 stars2 weeks ago
The house was well stocked, neat and clean. The property has lots of great outdoor space to relax in. Nataliya was very responsive. Thank you.
Guest favourite
Home in Hensonville
5 out of 5 average rating, 10 reviews

Perfect Windham & Hunter Ski House 2 Miles to Mntn

PeterRating, 5 stars2 months ago
One of the best Airbnbs I've stayed at. The house is amazing - spacious, cozy, ad each room had their own temperature control! Plenty of communal space and the kitchen was very functional. The hosts were so responsive and nice and even offered to mail a piece of clothing we had left at the house afterwards. Definitely would come back again and highly recommended.
Guest favourite
Home in Hunter Mountain, Hunter
4.96 out of 5 average rating, 104 reviews

Private Mountain Lodge, 10mins to Hunter & Windham

PaulRating, 5 stars2 months ago
My family's second visit to this beautiful gem overlooking the mountains and frozen pond. Our hosts are highly communicative and helpful. The description is accurate. Considering our 2nd visit and rebooked for 3rd in 2026 - this speaks volumes -- more than meets our needs, well stocked. We're looking forward to visiting during the summer months to further appreciate the views. Grateful to them for sharing their home with us.
Top guest favourite
Home in Athens
5 out of 5 average rating, 16 reviews

Lake house with arcade games

AdrienneRating, 5 stars3 months ago
Rosane and Daniel's place was great. Very clean and comfortable. It was well stocked with everything we needed.
Guest favourite
Cabin in Shandaken
4.99 out of 5 average rating, 104 reviews

A Place Called Home in The Catskill

KateRating, 5 stars1 month ago
We just finished a two month rental of John’s wonderful home. Our family of 5 used the home primarily on the weekends when we were enjoying ski season at Belleayre Mountain. I can’t say enough great things about this home. Our family felt totally at home - every aspect was perfectly maintained and the home maximized comfort. Our favorite part of the home was the great room where we would watch movies on the huge family sofa in front of a crackling fire. It was the perfect way to end a day of skiing. Our kids loved the downstairs family room with the foosball table and there were lots of games to play and keep everyone busy and entertained. And the kitchen is huge and very well stocked with all the appliances you will ever need. So it was a fantastic 2 months and we look forward to renting this property again!
Guest favourite
Home in Tannersville
4.93 out of 5 average rating, 28 reviews

Luxury Spacious Private Home w/tub! Enjoy Spring

SantiagoRating, 5 stars2 months ago
It’s a fantastic place to stay—a well-designed, private home with a great layout. Conveniently located near the mountain, it’s perfect for skiing while still offering a peaceful retreat.

Quick stats about holiday rentals in Windham

  • Total rentals

    160 properties

  • Nightly prices starting at

    £60 before taxes and fees

  • Total number of reviews

    6.2K reviews

  • Family-friendly rentals

    150 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Destinations to explore

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  2. United States
  3. New York
  4. Greene County
  5. Windham