If you’re one of those who like to spend most of the time outside, but also would like to relax to recharge, then you must visit the tiny New York town of Windham. Nestled between the Catskill Mountains of New York State, this town is renowned for Windham Mountain Resort that’s home to multiple ski trails and a mountain bike park. You’ll find several fun things to do in Windham. Whether you’re in the mood for a hike or just a walk, there is a plethora of mountains here to choose from. You’ll also find luxurious nature retreats and glamping spots near Kingston, less than an hour away from Windham. That said, whatever the reason may be for your visit, the place you stay is important. Hence, for a memorable experience, consider these best Airbnb vacation rentals in Windham, New York.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 09, 2024.
1. Elegant home on the main street (from USD 101)
When you’re on a vacation to a new city or a country, you must always live in style and comfort. And, this beautiful rental house in Windham does justice to that. This one-bedroom home can accommodate two guests. It also has a private bathroom and a fully equipped kitchen. What’s more? The complimentary internet will keep you connected 24/7. There’s a balcony over the main street, where you can enjoy the street views while drinking your coffee/tea. Some of the popular sights around the area are Windham Mountain, and Hayfield, and there are several restaurants and bars nearby as well.
Top guest reviews
Amenities & Room:
they probably have the most comfortable couch i've ever sat on and the beds are comfy toothe apartment itself is spacious warm clean and filled to the brim with amenitiesthere is also a rollaway bed which allowed space for my friend to join me over the weekendwe stayed for 4 nights and it was quiet and comfortablethe apartment was very clean and had all the amenities that i could really ask forCleanliness:
very clean and neatsuper clean and comfortablesuper clean and comfortablethe space was exceptionally clean as wellthe space is immaculately clean sweet and personalHost:
susan and kevin are great hostssusan was a great hostsusan is a wonderful hostsusan was an amazing hostit's a home from home with great and thoughtful hostsRead more reviewsLocation:
it was in a great location within walking distance to townthe apartment is located in the perfect spot walking distance to plenty of restaurants stores etcvery comfortable place in a great locationgreat value in a great locationvery relaxed environment with stores and restaurants in walking or very close driving distance
2. Stylish cabin with a hot tub
The vibrancy of this cozy vacation rental in Windham will pleasantly surprise you. It is great for a family or a group of friends traveling together. This stunning rental easily accommodates up to six guests and has three bedrooms with three queen-size beds. It also comprises a bathroom, a full kitchen, and a dining area. Enjoy evening shenanigans with your loved ones around by spending time in the backyard with a fire pit, or pamper yourself in the hot tub under the stars.
Windham, New York, United States
29.64 km (18.5 mi) from Belleayre Mountain Ski CenterSuperhost
Accommodates: 6
Top guest reviews
Amenities & Room:
it is so comfortable and cozy with thoughtful touches and amenities in every single roomstrong wifi we worked remotely during this time and had so issues cons1the house was cozy and clean and had all the amenities you could needfits 6 very comfortably with a great family room dining area and kitchenCleanliness:
very clean and comfortable spacethe house is great very clean and well maintainedgreat house clean well decoratedheather’s house was clean and thoughtfully decoratedthe place was very cleanHost:
she was a wonderful host and i would definitely recommend staying at her wonderful homethank you heather for being such a great hostheather was a really responsive hostheather was a great host: very responsive and super nicethe host has made great effort to create lighting ambientance throughout the home which we lovedRead more reviewsLocation:
great house in a great locationit’s a great location close to the mountain and downtowngreat place great location with an awesome hot tubgreat cozy cabin close to slopes and townawesome place with an amazing ski resort close by
3. Cute cabin for two (from USD 199)
Enjoy the beauty and serenity of nature, away from the hustle and bustle of the city, in this cabin, named the Cutest Cabin. This cabin was built by the Amish in Pennsylvania and is decorated adorably. The cabin features a front porch with a hot tub, a charming pine cathedral ceiling, and a fire pit and barbecue with Adirondack chairs. This one-bedroom vacation rental can comfortably accommodate two guests in its queen-size bed. There’s a frog pond nearby.
Top guest reviews
Cleanliness:
very clean and cozyextremely clean and tidythe cabin is very clean and comfortablevery nice new looking and cleanmy wife and i really appreciated how clean everything was as wellHost:
the host is amazing and kindtammy is a gracious and friendly host who accommodates her gueststammy was an amazing host from the very beginningthe cabin itself was very well appointed the hosts thought of everythingif you're interested in windham this property and host are greatRead more reviewsLocation:
great location near the mountainlocation was perfect for ustammy's place is in a great locationsuper close to windam mountain and the center of townperfect place for a weekend getaway the location is excellent
4. Log-style pet-friendly home (from USD 600)
Feel the warmth of this beautiful log-style home that can comfortably accommodate up to 11 guests in 3 bedrooms with 10 beds and 4 baths. This cabin has heated tile flooring on the lower level. It also includes a fully equipped kitchen, with a dining area and a fireplace. The entire home provides pristine views of Windham’s ski slopes. That’s not all! There’s an outdoor seating area, another dining area on the upper deck, a gas fire pit, and a barbecue. This home is also pet-friendly, and you’ll be happy to know that there’s a fenced-in area where your dogs can roam freely.
Top guest reviews
Amenities & Room:
all amenities and facilities were clean and fully functionalsolid location close to windham really pretty views and excellent kitchenCleanliness:
everything was very clean and checkin was incredibly easythe house was great beautiful and clean inside and outwe all had a comfortable place to sleep with clean sheets and towelsthe house was so clean and the jacuzzi is a bright spotvery clean comfortable and perfect locationHost:
debra was a fantastic hostdebra is a very gracious and helpful hostdebra was super responsive and helpfuldebra is a responsive hostdebra was extremely accommodating and responsiveRead more reviewsLocation:
great space close to mountainclose to trails restaurants and the cute town of windhamthis place is a secluded paradise and close enough to towngreat location away from the neighbors incredible housegreat place to stay convenient location too
5. A beautiful summer home with Windham Mountain views (from USD 595)
Situated just five minutes away from the Windham mountain, this brand new four-bedroom house is tastefully decorated with a stone fireplace, countertops made of granite, and large wooden doors. Every morning, you get to wake up to the blissful views of the ski slopes that you’ll get to witness through the large windows. It is equipped with all the modern amenities you could think of, making this a perfect place to spend your holidays year-round. Drink a fine glass of wine or a cup of coffee on the large balcony and call it a day!
Top guest reviews
Amenities & Room:
amazing view from the living/dining roomkitchen was fully stocked from a cookware point of view and the fire pit was great at nightgreat open space with lots of entertainment for the kids and the sleeping arrangements were very comfortablegreat place easy to find good location comfortable beds big kitchen great grill on the patiothe giant windows in the living room are a great touch to the houseCleanliness:
very clean and comfortablea beautiful clean quiet and comfortable homeprivate clean and very roomythe house is very spacious clean and beautifulthe house was very clean and the kids loved the games in the basementHost:
thank you for your hostamazing host with immediate responses to questionsthe hosts were very helpfulowners were wonderful and responded quickly to a few questionsfrank and karen are exceptional hosts with a wonderful homeRead more reviewsLocation:
great locationgreat location that is close to the village and skiinggreat location really close to the mountain and townexcellent place close to the mountainswonderful location right near town and the mountain
6. Renovated caboose in the city center (from USD 199)
Nestled in the city center, this renovated vacation rental features a rustic interior and exterior that sets a tone for itself. The first look of this rental is that of a train compartment. So, if you’ve ever dreamt of staying in a train compartment, here’s your alternative. And, a cool one! It comes with a bedroom and bathroom, and can accommodate up to two guests. It is also equipped with all the modern amenities to make your stay comfortable and convenient. You’re sure to have a unique experience when you stay here.
Top guest reviews
Cleanliness:
this was an awesome stay the inside was clean and well up keptthis adorable little place totally exceeded our expectations super clean & comfortable amazing location and friendly hostHost:
patrick was a great host; friendly and helpfulpatrick was a great host - went above and beyondpatrick is very kind and a great hostRead more reviewsLocation:
great location really nice place in a cute little town
7. Chic and stylish apartment (from USD 214)
When you stay at this beautiful apartment, you’ll get the vibe of “home away from home”. The one-bedroom Airbnb rental comprises everything you’d need in a comfortable home. Although this is a one-bedroom ski apartment, it can easily fit in up to five guests. You can also use all the facilities the house provides, such as the kitchen. It also has a good internet connection, TV, and free parking on the premises. If you’re an adventure junkie, you’ll be happy to know that you get access to the ski slopes and the adventure park, which is at a walking distance from this apartment.
Top guest reviews
Amenities & Room:
this apt was perfect for our family of three on a skiing weekenda great apartment for a small groupCleanliness:
it was clean and nicely doneclean and convenient for skiing at windhamapartment was clean and cozy and had everything we neededclean quiet and cutewe had a great visit the apartment was clean and had everything we neededHost:
thank you so much to our host for a wonderful staymaika was such a wonderful hostmaika was an amazing hosthost was very easy to work with and very prompt to respondhosts are very responsive and flexible they let us stay an extra hourRead more reviewsLocation:
great apartment in wonderful locationthe location couldn’t be betterthis is a wonderful place so close to the mountaincozy apt walking distance from windham mountain definitely recommendperfect location just a couple minutes from windham ski area
8. Centrally located house (from USD 200)
Located in the center of Windham, this cute little rental house can accommodate up to five guests, in two bedrooms with a double bed, a single bed, and two sofa beds. It also comes with a fully equipped kitchen, internet connection, free parking on-site, and TV, among other amenities. Because of its convenient location, you’re situated close to the city’s attractions, restaurants, pubs, and shops. Some of the attractions are Windham High Peak, Kate Hill, and The Vineyard at Windham, to name a few.
Top guest reviews
Cleanliness:
it is exceedingly clean and tidyit was clean and comfortablethis place was super clean warm and cozyfrom the small touches around the house to the cleanliness shows she caresa little additional to cleanliness such as dusting would have been greatHost:
host was very friendly and accommodatingmarta was a wonderful hostmarta was a very nice host and the house was beautiful and cozyand best of all super friendly and flexible hosts: 5-star hospitalitymarta was a fantastic hostRead more reviewsLocation:
super close to windhamit’s location was great very close to the mountain and walking distance to many restaurants and barscute guest house very close to windham ski mountainmarta’s place is in an optimal location in windhamoutside is less than a minute walk to windham’s great stores and restaurants
9. Spectacular penthouse with a sunroom (from USD 86)
When you stay in this penthouse, you’ll feel like you’re staying amidst the clouds. It’s a perfect place to unwind and relax during your vacation. Located just a stone’s throw away from the river, this penthouse boasts panoramic views of the mountains nearby. This two-bedroom penthouse is perfect for seven guests and also comprises two bathrooms, a kitchenette, a sunroom, and a living room. Visit the Windham Park, The Vineyard at Windham, and Elm Ridge Wild Forest that are located near the penthouse.
Top guest reviews
Cleanliness:
we rented two spaces in the same building and they were each unique clean well-equipped and spacioussuzanne's place was very stylish and clean and it was in such a convenient location as wellsuzanne's place is spacious clean and has a great locationHost:
suzanna was a wonderful hostexcellent communication from host and who called to let us know we had left some items behindthe place has enough rooms to accommodate large families and it is kid friendlyRead more reviewsLocation:
great location and very hospitableher place is walking distance to some great local restaurants and storesa great place conveniently located -- we would come againthe place worked out perfectlythe location is incredibly convenient the space is really nice and suzanne was extremely responsive
10. Modern home with a garden
You’re sure to have an amazing vacation when you book this rental. You get excellent quality internet and cell phone service, making it easier for you if you’re working remotely. Along with this, this four-bedroom home is within walking distance from all the restaurants, and a quick ride will take you to Windham and Hunter ski mountains. There’s plenty of room to accommodate 12 guests comfortably. The rustic design of the home along with exposed beams offers warmth to the entire place. There’s also a large deck with two picnic tables and a fire pit to spend a lovely day.
Windham, New York, United States
28.32 km (17.6 mi) from Belleayre Mountain Ski CenterAccommodates: 8
Top guest reviews
Amenities & Room:
tv works great for movies there’s board games and a great fireplace for a cozy night inCleanliness:
very clean home with a very cool trendy decorating styleso many beds all rooms sparkley cleanHost:
host was very responsive with any questions we hadjeni was a wonderful hostoverall great stay with a great hostsuper convenient great spaces and comfortable living great hostsenjoyed our stay we had plenty of room for the kids and host was very helpfulRead more reviewsLocation:
great place within good proximity to where we needed to bejeni's place is in the perfect location
Enjoy the luxury of the mountains and the city
Whether you want to stay near the mountainside or in the city center, Windham has got it all for you. From panoramic views of the mountains to various cafes and restaurants in the city, staying at these Airbnb rentals will give you a once-in-a-lifetime experience.
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