10 Best Airbnb Vacation Rentals In Windham, New York - Updated 2022

Aarti
Aarti 
Updated

If you’re one of those who like to spend most of the time outside, but also would like to relax in order 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. Whether you’re in the mood for a hike, or just a walk, there are a plethora of mountains here to choose from. Along with this, you can also go on a shopping spree as there are a lot of shops in the area. That said, whatever the reason may be for your visit, the place you stay is important. Hence, consider these best Airbnb vacation rentals in Windham, New York, for a memorable experience.

1. Elegant home on the main street (from USD 96)

When you’re on a vacation to a new city or a country, one must always live in style and comfort. And, this beautiful home does justice to that. This one-bedroom home can accommodate two guests. It also has its own 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.

Main Street, The Heart of Windham
Windham, New York, United States
148 reviews Superhost  Wifi Available
Entire rental unit 2 Beds 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
they probably have the most comfortable couch i've ever sat on and the beds are comfy too
the apartment itself is spacious warm clean and filled to the brim with amenities
there is also a rollaway bed which allowed space for my friend to join me over the weekend
we stayed for 4 nights and it was quiet and comfortable
the apartment was very clean and had all the amenities that i could really ask for
Cleanliness:
very clean and neat
super clean and comfortable
super clean and comfortable
the space was exceptionally clean as well
the space is immaculately clean sweet and personal
Host:
susan and kevin are great hosts
susan was a great host
susan is a wonderful host
susan was an amazing host
it's a home from home with great and thoughtful hosts
Location:
it was in a great location within walking distance to town
the apartment is located in the perfect spot walking distance to plenty of restaurants stores etc
very comfortable place in a great location
great value in a great location
very relaxed environment with stores and restaurants in walking or very close driving distance
Read more reviews

2. Stylish cabin with a hot tub (from USD 309)

The vibrancy of this cozy cabin 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.

Cozy Cabin With Hot Tub Under The Stars
Windham, New York, United States
135 reviews Superhost  Wifi Available
Entire cabin 3 Beds 6 Guests 3 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
it is so comfortable and cozy with thoughtful touches and amenities in every single room
strong wifi we worked remotely during this time and had so issues cons1
the house was cozy and clean and had all the amenities you could need
fits 6 very comfortably with a great family room dining area and kitchen
Cleanliness:
very clean and comfortable space
the house is great very clean and well maintained
great house clean well decorated
heather’s house was clean and thoughtfully decorated
the place was very clean
Host:
she was a wonderful host and i would definitely recommend staying at her wonderful home
thank you heather for being such a great host
heather was a really responsive host
heather was a great host: very responsive and super nice
the host has made great effort to create lighting ambientance throughout the home which we loved
Location:
great house in a great location
it’s a great location close to the mountain and downtown
great place great location with an awesome hot tub
great cozy cabin close to slopes and town
awesome place with an amazing ski resort close by
Read more reviews

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.

Cutest Cabin w/BBQ Grill, fire pit, trail to pond
Windham, New York, United States
75 reviews  Wifi Available
Tiny home 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Cleanliness:
very clean and cozy
extremely clean and tidy
the cabin is very clean and comfortable
very nice new looking and clean
my wife and i really appreciated how clean everything was as well
Host:
the host is amazing and kind
tammy is a gracious and friendly host who accommodates her guests
tammy was an amazing host from the very beginning
the cabin itself was very well appointed the hosts thought of everything
if you're interested in windham this property and host are great
Location:
great location near the mountain
location was perfect for us
tammy's place is in a great location
super close to windam mountain and the center of town
perfect place for a weekend getaway the location is excellent
Read more reviews

4. Log-style pet-friendly home (from USD 556)

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.

Windham Luxury Pet Friendly Retreat
Windham, New York, United States
87 reviews  Wifi Available
Entire home 10 Beds 11 Guests 3 Bedrooms 4 Bathrooms

Accommodates: 11

Top guest reviews
Amenities & Room:
all amenities and facilities were clean and fully functional
solid location close to windham really pretty views and excellent kitchen
Cleanliness:
everything was very clean and checkin was incredibly easy
the house was great beautiful and clean inside and out
we all had a comfortable place to sleep with clean sheets and towels
the house was so clean and the jacuzzi is a bright spot
very clean comfortable and perfect location
Host:
debra was a fantastic host
debra is a very gracious and helpful host
debra was super responsive and helpful
debra is a responsive host
debra was extremely accommodating and responsive
Location:
great space close to mountain
close to trails restaurants and the cute town of windham
this place is a secluded paradise and close enough to town
great location away from the neighbors incredible house
great place to stay convenient location too
Read more reviews

5. A beautiful summer home with Windham Mountain views (from USD 428)

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!

Beautiful Windham Ski/Summer House
156 reviews Superhost  Wifi Available
Entire chalet 7 Beds 10 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
amazing view from the living/dining room
kitchen was fully stocked from a cookware point of view and the fire pit was great at night
great open space with lots of entertainment for the kids and the sleeping arrangements were very comfortable
great place easy to find good location comfortable beds big kitchen great grill on the patio
the giant windows in the living room are a great touch to the house
Cleanliness:
very clean and comfortable
a beautiful clean quiet and comfortable home
private clean and very roomy
the house is very spacious clean and beautiful
the house was very clean and the kids loved the games in the basement
Host:
thank you for your host
amazing host with immediate responses to questions
the hosts were very helpful
owners were wonderful and responded quickly to a few questions
frank and karen are exceptional hosts with a wonderful home
Location:
great location
great location that is close to the village and skiing
great location really close to the mountain and town
excellent place close to the mountains
wonderful location right near town and the mountain
Read more reviews

6. Modern home with a garden (from USD 230)

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 Mountain House Huge Deck Walkable to Town
Windham, New York, United States
59 reviews Superhost  Wifi Available
Entire home 4 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
tv works great for movies there’s board games and a great fireplace for a cozy night in
Cleanliness:
very clean home with a very cool trendy decorating style
so many beds all rooms sparkley clean
Host:
host was very responsive with any questions we had
jeni was a wonderful host
overall great stay with a great host
super convenient great spaces and comfortable living great hosts
enjoyed our stay we had plenty of room for the kids and host was very helpful
Location:
great place within good proximity to where we needed to be
jeni's place is in the perfect location
Read more reviews

7. Renovated caboose in the city center (from USD 225)

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.

Cozy, restored 1922 Caboose in center of Windham
81 reviews Superhost  Wifi Available
Tiny home 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Cleanliness:
this was an awesome stay the inside was clean and well up kept
this adorable little place totally exceeded our expectations super clean & comfortable amazing location and friendly host
Host:
patrick was a great host; friendly and helpful
patrick was a great host - went above and beyond
patrick is very kind and a great host
Location:
great location really nice place in a cute little town
Read more reviews

8. Chic and stylish apartment (from USD 189)

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.

Mountainside Ski Deluxe Windham Apt - 1Br 1Bath
Windham, New York, United States
70 reviews  Wifi Available
Entire rental unit 5 Beds 5 Guests 1 Bedroom 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
this apt was perfect for our family of three on a skiing weekend
a great apartment for a small group
Cleanliness:
it was clean and nicely done
clean and convenient for skiing at windham
apartment was clean and cozy and had everything we needed
clean quiet and cute
we had a great visit the apartment was clean and had everything we needed
Host:
thank you so much to our host for a wonderful stay
maika was such a wonderful host
maika was an amazing host
host was very easy to work with and very prompt to respond
hosts are very responsive and flexible they let us stay an extra hour
Location:
great apartment in wonderful location
the location couldn’t be better
this is a wonderful place so close to the mountain
cozy apt walking distance from windham mountain definitely recommend
perfect location just a couple minutes from windham ski area
Read more reviews

9. Centrally located house (from USD 180)

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.

Small house, Windham, NY
117 reviews Superhost  Wifi Available
Entire home 4 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Cleanliness:
it is exceedingly clean and tidy
it was clean and comfortable
this place was super clean warm and cozy
from the small touches around the house to the cleanliness shows she cares
a little additional to cleanliness such as dusting would have been great
Host:
host was very friendly and accommodating
marta was a wonderful host
marta was a very nice host and the house was beautiful and cozy
and best of all super friendly and flexible hosts: 5-star hospitality
marta was a fantastic host
Location:
super close to windham
it’s location was great very close to the mountain and walking distance to many restaurants and bars
cute guest house very close to windham ski mountain
marta’s place is in an optimal location in windham
outside is less than a minute walk to windham’s great stores and restaurants
Read more reviews

10. Spectacular penthouse with a sunroom (from USD 89)

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.

Studio 3 BEDS-SLEEP 4
Windham, New York, United States
56 reviews Superhost  Wifi Available
Entire condo 3 Beds 3 Guests 2 Bedrooms 1 Bathroom

Accommodates: 3

Top guest reviews
Cleanliness:
we rented two spaces in the same building and they were each unique clean well-equipped and spacious
suzanne's place was very stylish and clean and it was in such a convenient location as well
suzanne's place is spacious clean and has a great location
Host:
suzanna was a wonderful host
excellent communication from host and who called to let us know we had left some items behind
the place has enough rooms to accommodate large families and it is kid friendly
Location:
great location and very hospitable
her place is walking distance to some great local restaurants and stores
a great place conveniently located -- we would come again
the place worked out perfectly
the location is incredibly convenient the space is really nice and suzanne was extremely responsive
Read more reviews

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.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Born in Mumbai and brought up in Bangalore, India, Aarti is a full-time freelance writer by profession. She is a lover of everything the ‘blue dot’ offers—world cultures, off-the-beaten tracks,...Read more

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