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Featured weekend hotel deals in Windham




The Winwood Condominiums
The Winwood CondominiumsWindham
8.8 out of 10, Excellent, (369 reviews)
8.8/10
Excellent
(369 reviews)
$278 nightly
The price is $601
$601 total
Oct 23 - Oct 25
Total with taxes and fees




Cave Mountain Motel
Cave Mountain MotelWindham
9.4 out of 10, Exceptional, (151 reviews)
9.4/10
Exceptional
(151 reviews)
$159 nightly
The price is $343
$343 total
Oct 23 - Oct 25
Total with taxes and fees




2 Mi to Windham Mountain: Scenic Home w/ Fire Pit!
2 Mi to Windham Mountain: Scenic Home w/ Fire Pit!Windham
4.0 out of 10, (2 reviews)
4.0/10
(2 reviews)
$346 nightly
The price is $747
$747 total
Oct 23 - Oct 25
Total with taxes and fees




The Haüs Windham
The Haüs WindhamWindham
8.0 out of 10, Very good, (39 reviews)
8.0/10
Very good
(39 reviews)
$804 nightly
The price is $1,737
$1,737 total
Oct 23 - Oct 25
Total with taxes and fees




Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House
Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain HouseWindham
$1,034 nightly
The price is $2,233
$2,233 total
Oct 23 - Oct 25
Total with taxes and fees




Ski, Hike & More: Year-round Gem in Windham
Ski, Hike & More: Year-round Gem in WindhamWindham
$548 nightly
The price is $1,183
$1,183 total
Oct 23 - Oct 25
Total with taxes and fees




Grand Windham Retreat w/ Fire Pit & Game Room
Grand Windham Retreat w/ Fire Pit & Game RoomWindham
$638 nightly
The price is $1,379
$1,379 total
Oct 23 - Oct 25
Total with taxes and fees
Check out pet-friendly hotels in Windham




9.4 out of 10, Exceptional, (888)
9.4/10
Exceptional
(888)
$145 nightly
The price is $157
$157 total
Oct 29 - Oct 30
Total with taxes and fees




8.8 out of 10, Excellent, (133)
8.8/10
Excellent
(133)
$225 nightly
The price is $243
$243 total
Oct 30 - Oct 31
Total with taxes and fees




9.2 out of 10, Wonderful, (121)
9.2/10
Wonderful
(121)
$254 nightly
The price is $273
$273 total
Nov 19 - Nov 20
Total with taxes and fees




8.0 out of 10, Very good, (39)
8.0/10
Very good
(39)
$299 nightly
The price is $323
$323 total
Nov 17 - Nov 18
Total with taxes and fees




1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mtn
1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham MtnWindham
7.6 out of 10, Good, (5)
7.6/10
Good
(5)
$190 nightly
The price is $216
$216 total
Oct 20 - Oct 21
Total with taxes and fees




Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets WelcomeWindham
9.6 out of 10, Exceptional, (8)
9.6/10
Exceptional
(8)
$475 nightly
The price is $513
$513 total
Oct 21 - Oct 22
Total with taxes and fees




Pines Vignette • Modern 3BR Home in Windham
Pines Vignette • Modern 3BR Home in WindhamWindham
10.0 out of 10, Exceptional, (2)
10/10
Exceptional
(2)
$482 nightly
The price is $521
$521 total
Oct 20 - Oct 21
Total with taxes and fees




Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain
Secluded Glass Cabin in the Woods, 3 Minutes to Windham MountainWindham
7.6 out of 10, Good, (5)
7.6/10
Good
(5)
$243 nightly
The price is $276
$276 total
Oct 26 - Oct 27
Total with taxes and fees




Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC
Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMCWindham
10.0 out of 10, Exceptional, (1)
10/10
Exceptional
(1)
$685 nightly
The price is $740
$740 total
Oct 20 - Oct 21
Total with taxes and fees




Tiny House on Walnut Grove
Tiny House on Walnut GroveAshland
4.0 out of 10, (2)
4.0/10
(2)
$401 nightly
The price is $433
$433 total
Oct 20 - Oct 21
Total with taxes and fees
Hotels with a pool in Windham may fit your trip




9.4 out of 10, Exceptional, (888)
9.4/10
Exceptional
(888)
$145 nightly
The price is $157
$157 total
Oct 29 - Oct 30
Total with taxes and fees




8.8 out of 10, Excellent, (369)
8.8/10
Excellent
(369)
$167 nightly
The price is $180
$180 total
Oct 25 - Oct 26
Total with taxes and fees




8.8 out of 10, Excellent, (133)
8.8/10
Excellent
(133)
$225 nightly
The price is $243
$243 total
Oct 30 - Oct 31
Total with taxes and fees




Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets WelcomeWindham
9.6 out of 10, Exceptional, (8)
9.6/10
Exceptional
(8)
$475 nightly
The price is $513
$513 total
Oct 21 - Oct 22
Total with taxes and fees




Condo in Windham Mountain Village
Condo in Windham Mountain VillageWindham
10.0 out of 10, Exceptional, (16)
10/10
Exceptional
(16)
$916 nightly
The price is $989
$989 total
Oct 20 - Oct 21
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.
Top Windham Hotel Reviews




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




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




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




Jimmy OConnors Windham Mountain Inn
Jimmy OConnors Windham Mountain InnWindham
10/10 Excellent
I have stayed at well over a dozen motels, hotels, lodges, resorts over my time in the Catskills. This was by far one of my favorites and is almost certainly going to become my regular resting spot. The location is premium, with it located in the heart of the Catskills, and not far from most attractions and hikes. The bar itself serves great food and drinks, and Sean and the staff are a delight to speak to. The room is clean, well maintained, and the cleaning staff do a great job each day. Most...
I have stayed at well over a dozen motels, hotels, lodges, resorts over my time in the Catskills. This was by far one of my favorites and is almost certainly going to become my regular resting spot. The location is premium, with it located in the heart of the Catskills, and not far from most attractions and hikes. The bar itself serves great food and drinks, and Sean and the staff are a delight to speak to. The room is clean, well maintained, and the cleaning staff do a great job each day. Most...
Asher




Antique Rose Inn Windham
Antique Rose Inn WindhamWindham
10/10 Excellent
Was a very pleasant stay and the proprietor is very kind.
Was a very pleasant stay and the proprietor is very kind.
Anonymous traveler




Wylder Hotel Windham
Wylder Hotel WindhamWindham
10/10 Excellent
Cozy stay
Cozy stay
Rashmi Rajkumar




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




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




Deer Mountain Inn
Deer Mountain InnHaines Falls
10/10 Excellent
Staff made you feel right at home, the server had immense knowledge in the food they were serving! You can also taste the chef’s effort that he put into each dish! I will definitely be back.
Staff made you feel right at home, the server had immense knowledge in the food they were serving! You can also taste the chef’s effort that he put into each dish! I will definitely be back.
Elizabeth




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




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




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




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




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
