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Find vacation rentals that suit your style

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Chalets

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Our top choices for Windham chalets




1. Beautiful Windham Chalet 2 minutes to Town and the Mountain
Beautiful Windham Chalet 2 minutes to Town and the MountainWindham
10.0 out of 10, Exceptional, (3 reviews)
10/10
Exceptional
(3 reviews)
"Very easy to check in and check out. Very excellent instructions and welcoming atmosphere. "
"Very easy to check in and check out. Very excellent instructions and welcoming atmosphere. "John K.
$583 nightly
The price is $629
$629 total
Nov 17 - Nov 18
Total with taxes and fees




2. Relaxing Mountain Hideaway - Hot Tub & Outdoors
Relaxing Mountain Hideaway - Hot Tub & OutdoorsHensonville
10.0 out of 10, Exceptional, (3 reviews)
10/10
Exceptional
(3 reviews)
"Great house and great host! Very convenient location particularly to Windham Mountain. "
"Great house and great host! Very convenient location particularly to Windham Mountain. "Kyrill A.
$551 nightly
The price is $595
$595 total
Nov 16 - Nov 17
Total with taxes and fees




3. Jessie's Harvest House
Jessie's Harvest HouseTannersville
8.4 out of 10, Very good, (7 reviews)
8.4/10
Very good
(7 reviews)
"cute little spot! very nice place to stay"
"cute little spot! very nice place to stay"David R.
$181 nightly
The price is $191
$191 total
Nov 15 - Nov 16
Total with taxes and fees




4. Jessie's Harvest House
Jessie's Harvest HouseTannersville
2.0 out of 10, (1 review)
2.0/10
(1 review)
"We pulled up to a restaurant inn with not a soul in sight. The restaurant was closed with a for sale Realastate sign outside. There place had broken windows and a side back door to access . We walked in to find a dark room with an old piano . We went upstairs to see the room and the only thing in the rooms posted was the white sheets and blankets . There was a small area with a microwave outside our door . The pictures had an outside sitting for guests that was not the case . We left and ended...
"We pulled up to a restaurant inn with not a soul in sight. The restaurant was closed with a for sale Realastate sign outside. There place had broken windows and a side back door to access . We walked in to find a dark room with an old piano . We went upstairs to see the room and the only thing in the rooms posted was the white sheets and blankets . There was a small area with a microwave outside our door . The pictures had an outside sitting for guests that was not the case . We left and ended...Genine B.
$181 nightly
The price is $191
$191 total
Nov 13 - Nov 14
Total with taxes and fees




5. Jessie's Harvest House
Jessie's Harvest HouseTannersville
$180 nightly
The price is $190
$190 total
Nov 13 - Nov 14
Total with taxes and fees




6. Jessie's Harvest House
Jessie's Harvest HouseTannersville
8.0 out of 10, Very good, (1 review)
8.0/10
Very good
(1 review)
$181 nightly
The price is $191
$191 total
Nov 13 - Nov 14
Total with taxes and fees




7. Jessie's Harvest House
Jessie's Harvest HouseTannersville
$180 nightly
The price is $190
$190 total
Nov 13 - Nov 14
Total with taxes and fees




8. Jessie's Harvest House Suite
Jessie's Harvest House SuiteTannersville
9.0 out of 10, Wonderful, (8 reviews)
9.0/10
Wonderful
(8 reviews)
"Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer."
"Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer."Matthew M.
$177 nightly
The price is $187
$187 total
Dec 8 - Dec 9
Total with taxes and fees




9. Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski BelleayreBig Indian
9.8 out of 10, Exceptional, (30 reviews)
9.8/10
Exceptional
(30 reviews)
"Room was spotless and amenities were great."
"Room was spotless and amenities were great."Richard
$691 nightly
The price is $774
$774 total
Nov 16 - Nov 17
Total with taxes and fees
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.
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.
Learn more about Windham
Nestled in the Catskills, this mountain town transforms from a powdery ski paradise to a lush hiking haven with seasons. Visit Windham Mountain for thrilling slopes in winter or explore the scenic Rail Trail when summer's wildflowers frame perfect mountain views.

Top reviews in Windham




Shandaken Inn
Shandaken InnShandaken
10/10 Excellent
The Shandaken Inn is a gem of a property! Our room was spacious, spotless and so inviting. And the staff, particularly Marissa, made us feel so welcome and at home with her warm personality.
The breakfasts were outstanding and the entire property is just beautiful! There are also great hiking options close by. We wouldn’t hesitate to book a room here again!
The Shandaken Inn is a gem of a property! Our room was spacious, spotless and so inviting. And the staff, particularly Marissa, made us feel so welcome and at home with her warm personality.
The breakfasts were outstanding and the entire property is just beautiful! There are also great hiking options close by. We wouldn’t hesitate to book a room here again!
Anonymous traveler




Gather Greene
Gather GreeneCoxsackie
10/10 Excellent
This place was magical. Rooms were clean. Same amenities as a hotel. Blow dryer available! Mini fridge and a sheet for blinds if you need. The snow falling in the early morning was the highlight of the cabin stay. Very beautiful! There were two campfires and snores every night from 5-1pm. Very cute! Cabins are about 50-100ft from parking so be prepared to walk in snow after parking your care. You can get closer to a loading zone to load things into and out of cabins if needed though. String...
This place was magical. Rooms were clean. Same amenities as a hotel. Blow dryer available! Mini fridge and a sheet for blinds if you need. The snow falling in the early morning was the highlight of the cabin stay. Very beautiful! There were two campfires and snores every night from 5-1pm. Very cute! Cabins are about 50-100ft from parking so be prepared to walk in snow after parking your care. You can get closer to a loading zone to load things into and out of cabins if needed though. String...
Liana




Hotel Mountain Brook
Hotel Mountain BrookTannersville
10/10 Excellent
Great experience, amazing property,
Great experience, amazing property,
Nikolaos




Shadowcrest
ShadowcrestFleischmanns
10/10 Excellent
Please has old authentic charm
Please has old authentic charm
Elena




Twin Gables of Woodstock
Twin Gables of WoodstockWoodstock
10/10 Excellent
One of the coolest and most accommodating places I have ever stayed. If you are coming to Woodstock are even thinking about it this is the place for you. All the rooms are unique, they are super clean and look exactly like they do online. The owner is amazing and she will point you in the right direction for whatever you are looking to do in town. Seriously cannot recommend enough and can’t wait to come back.
One of the coolest and most accommodating places I have ever stayed. If you are coming to Woodstock are even thinking about it this is the place for you. All the rooms are unique, they are super clean and look exactly like they do online. The owner is amazing and she will point you in the right direction for whatever you are looking to do in town. Seriously cannot recommend enough and can’t wait to come back.
Noah




Albergo Allegria Hotel
Albergo Allegria HotelWindham
10/10 Excellent
This is the third time we have stayed here over Thankgiving while visiting relatives in the area. it is such a quiet lovely old house and the owners are very accomodating and exteemly nice. Lots of room, very comfy living room with fireplace and big chairs. The included breakfast is fantastic. The kitchen is always open for tea and homemade cookies. Scent free linens and towels a huge plus.
This is the third time we have stayed here over Thankgiving while visiting relatives in the area. it is such a quiet lovely old house and the owners are very accomodating and exteemly nice. Lots of room, very comfy living room with fireplace and big chairs. The included breakfast is fantastic. The kitchen is always open for tea and homemade cookies. Scent free linens and towels a huge plus.
NH couple




The Colonial Motel
The Colonial MotelGrand Gorge
10/10 Excellent
Step back in time when a place to stay was charming, clean and had an owner who was actually on property and cared about your stay and well being.
If you’re looking for the above and a little mystic, look no further. This place has history that comes along with the beautiful well appointed room. Just an all out classy mix of antique furnishings as well as modern touches like an internet connection that works, in room Keurig coffee maker , comfortable bed and clean bathroom.
Our only regret was...
Step back in time when a place to stay was charming, clean and had an owner who was actually on property and cared about your stay and well being.
If you’re looking for the above and a little mystic, look no further. This place has history that comes along with the beautiful well appointed room. Just an all out classy mix of antique furnishings as well as modern touches like an internet connection that works, in room Keurig coffee maker , comfortable bed and clean bathroom.
Our only regret was...
Paula




Hotel Vienna
Hotel ViennaWindham
10/10 Excellent
cute hotel
close to mountain and amenities
cute hotel
close to mountain and amenities
michael




The Perch Hotel
The Perch HotelEast Windham
10/10 Excellent
A Hidden Gem with Million-Dollar Views!
We had such a magical stay at The Perch Hotel in East Windham! The view alone is worth the trip — on a clear day, you can see FIVE states from the property. Yes, five! It’s absolutely breathtaking and made for the perfect backdrop to relax and soak in the Catskills air.
The vibe of the hotel is something special — a perfect blend of modern comfort and mid-century charm that instantly transported me back to the golden era of Catskill tourism. It’s stylish...
A Hidden Gem with Million-Dollar Views!
We had such a magical stay at The Perch Hotel in East Windham! The view alone is worth the trip — on a clear day, you can see FIVE states from the property. Yes, five! It’s absolutely breathtaking and made for the perfect backdrop to relax and soak in the Catskills air.
The vibe of the hotel is something special — a perfect blend of modern comfort and mid-century charm that instantly transported me back to the golden era of Catskill tourism. It’s stylish...
Emmi




Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott BonvoyCatskill
10/10 Excellent
Perfect place to stay during a house hunt in the area. Great for pups too!
Perfect place to stay during a house hunt in the area. Great for pups too!
Leslie




Meadowood Inn
Meadowood InnArkville
10/10 Excellent
A really nice stay and a friendly host. Tanya had good suggestions for places to eat, visit, etc. and made delicious breakfasts. She even lent me an extension cord when the venue where my band was playing didn’t have one. The rooms were great and we had our own private bath. Highly recommend!
A really nice stay and a friendly host. Tanya had good suggestions for places to eat, visit, etc. and made delicious breakfasts. She even lent me an extension cord when the venue where my band was playing didn’t have one. The rooms were great and we had our own private bath. Highly recommend!
John




Cave Mountain Motel
Cave Mountain MotelWindham
10/10 Excellent
Cozy,clean and cute place, great host!
Cozy,clean and cute place, great host!
Petra




Mountain Treasure B&B
Mountain Treasure B&BMaplecrest
10/10 Excellent
We had stayed for two nights at this hotel . Place is Nice and Cozy makes you feel like you at home )
The owner is Very friendly and cooks delicious breakfast 😋
I would defently stay there again
We had stayed for two nights at this hotel . Place is Nice and Cozy makes you feel like you at home )
The owner is Very friendly and cooks delicious breakfast 😋
I would defently stay there again
Alina




Urban Cowboy Lodge
Urban Cowboy LodgeBig Indian
10/10 Excellent
A slice of heaven. From Buddys warm greeting to everyone on staff they are just the nicest, most witty and welcoming staff I’ve ever seen, without being pretentious. The chef hits it out of the park, creative and expertly prepared and freshly sourced. We will be back to relax and decompress again.A wonderful experience sinking into feather beds and Pendleton robes.
A slice of heaven. From Buddys warm greeting to everyone on staff they are just the nicest, most witty and welcoming staff I’ve ever seen, without being pretentious. The chef hits it out of the park, creative and expertly prepared and freshly sourced. We will be back to relax and decompress again.A wonderful experience sinking into feather beds and Pendleton robes.
Carolena




Eastwind Oliverea Valley
Eastwind Oliverea ValleyBig Indian
10/10 Excellent
Such a special and magical destination
Such a special and magical destination
Claire




Howland House
Howland HouseMount Tremper
10/10 Excellent
A very nice experience, the Howland House is a very charming guesthouse with cozy, rooms, an excellent restaurant, Oliver’s, right downstairs and a really welcoming atmosphere. Staff were helpful and friendly, really couldn’t have asked for a nicer stay. We had a standard room with a shared bathroom, but the way it was setup made it totally comfortable. Highly recommended place if you’re in the area and we’ll almost certainly return.
A very nice experience, the Howland House is a very charming guesthouse with cozy, rooms, an excellent restaurant, Oliver’s, right downstairs and a really welcoming atmosphere. Staff were helpful and friendly, really couldn’t have asked for a nicer stay. We had a standard room with a shared bathroom, but the way it was setup made it totally comfortable. Highly recommended place if you’re in the area and we’ll almost certainly return.
Ira
