Hotels in Windham
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Sep 6 - Sep 7Tomorrow
Sep 7 - Sep 8Next weekend
Sep 11 - Sep 13In two weeks
Sep 18 - Sep 20Where to stay in Windham?
The Winwood Condominiums
The Winwood CondominiumsWindham
$169
$183 total
includes taxes & fees
Sep 7 - Sep 8
Albergo Allegria Hotel
Albergo Allegria HotelWindham
$174
$188 total
includes taxes & fees
Sep 7 - Sep 8
Jimmy OConnors Windham Mountain Inn
Jimmy OConnors Windham Mountain InnWindham
$134
$144 total
includes taxes & fees
Oct 6 - Oct 7
Cave Mountain Motel
Cave Mountain MotelWindham
$139
$150 total
includes taxes & fees
Oct 1 - Oct 2
Antique Rose Inn Windham
Antique Rose Inn WindhamWindham
$135
$146 total
includes taxes & fees
Sep 8 - Sep 9
Eastwind Windham
Eastwind WindhamWindham
$289
$344 total
includes taxes & fees
Sep 7 - Sep 8
The Haüs Windham
The Haüs WindhamWindham
$135
$295 total
includes taxes & fees
Sep 30 - Oct 1
Wylder Hotel Windham
Wylder Hotel WindhamWindham
$256
$326 total
includes taxes & fees
Sep 7 - Sep 8
Hunter Lodge, a Bluebird by Lark
Hunter Lodge, a Bluebird by LarkHunter
$127
$158 total
includes taxes & fees
Sep 15 - Sep 16
The Perch Hotel
The Perch HotelEast Windham
$187
$202 total
includes taxes & fees
Sep 10 - Sep 11
Mountain Treasure B&B
Mountain Treasure B&BMaplecrest
$169
$183 total
includes taxes & fees
Sep 10 - Sep 11
Moore's Motel
Moore's MotelPrattsville
$120
$130 total
includes taxes & fees
Sep 7 - Sep 8
SunView Motel
SunView MotelTannersville
$118
$128 total
includes taxes & fees
Oct 1 - Oct 2
The Colonial Motel
The Colonial MotelGrand Gorge
$89
$98 total
includes taxes & fees
Sep 16 - Sep 17
Kaatskill Mountain Club & Condos by Vail Resorts
Kaatskill Mountain Club & Condos by Vail ResortsHunter
$198
$235 total
includes taxes & fees
Sep 7 - Sep 8
Hotel Mountain Brook
Hotel Mountain BrookTannersville
$179
$193 total
includes taxes & fees
Sep 7 - Sep 8
Black Bear Lodge
Black Bear LodgePrattsville
$149
$161 total
includes taxes & fees
Sep 7 - Sep 8
Windham NY Escape
Windham NY EscapeHensonville
$429
$542 total
includes taxes & fees
Sep 10 - Sep 11
Go beyond your typical stay in Windham
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Cottage
Family friendly
Our prices for hotels in Windham are cheapest in September
Our prices for hotels in Windham are cheapest in September
Price trends for hotels in Windham
Pricing is based on two traveler single night rates
Top landmarks in Windham
Windham Mountain Resort
9.0/10 (313 reviews)
Skiers and snowboarders might want to test out the slopes at Windham Mountain Resort, a skiing spot located 1.2 mi (1.9 km) from central Windham. If you master the slopes, Hunter Mountain and Mountain Trails Cross Country Ski and Snowshoe Center are also just a short drive away.
Windham Country Club
8.4/10 (20 reviews)
You might want to practice your swing at Windham Country Club, a golf course located 1 mi (1.6 km) from central Windham.
Windham Vineyards and Winery
9.0/10 (15 reviews)
Travelers might want a tour of Windham Vineyards and Winery, just one of the places to visit, and located 3.4 mi (5.4 km) from central Windham.
Ashland Park
Ashland Park is 4.4 mi (7 km) from central Windham, why not stop by during your stay.
Huntersfield State Forest
Huntersfield State Forest is 6.2 mi (9.9 km) from central Windham, why not stop by during your stay.
Elm Ridge Wild Forest
Elm Ridge Wild Forest is 3.5 mi (5.7 km) from central Windham, why not stop by during your stay.
Learn more about Windham
Tucked into the Catskills, this mountain hamlet transforms with the seasons. Carve fresh powder at Windham Mountain Resort in winter, where the slopes welcome skiers of all abilities. Summer brings hikers to scenic trails throughout Catskill State Park, with panoramic vistas worth every uphill step. The Windham Country Club offers 18 challenging holes for golfers seeking mountain backdrops with their birdies. After outdoor adventures, explore the quaint downtown where coffeehouses serve perfect post-adventure refreshments. Wine enthusiasts can sample local vintages at Windham Vineyards and Winery. For additional outdoor pursuits, nearby Hunter Mountain provides more terrain to explore, while Huntersfield State Forest offers quieter woodland escapes away from the resort crowds.
See all hotels in Windham
Check out reviews of Windham hotels guests love
AutoCamp Catskills
10/10 Excellent
"The check in Staff Chiara was very helpful to move the airstream next to my friend’s family even though it was full occupancy so we can do the bbq together. Well equipped to a bbq without bringing the gear and utensils."
Hotel Vienna
8/10 Good
"Clean , comfortable , did not use amenities bc we arrived too late . They had an indoors pool , a couple of places where you could make and sit by the fire and a corn hall . Breakfast was ok . Cereals, variety of coffees or tea . Various croissants and yougurt !"
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
10/10 Excellent
"It’s as beautiful as described online. We love the views and all the stuff provided, even though it’s a very compact cabin setting. Every thing is good. Only one thing scared me is some ants and small insects suddenly came out from no where. Outside has mosquitoes. But if you remember it’s in a nature forest, then they should be normal. Staff are very caring and thoughtful. They provide everything we need, and even more. We are very thankful for this opportunity to be there for enjoy."
Kaatskill Mountain Club & Condos by Vail Resorts
10/10 Excellent
"Great location to amazing trails and great accommodations"
Hunter Lodge, a Bluebird by Lark
10/10 Excellent
"This is the second time we have come here and it was nice that we just happened to stay in the same room as last time. This is such a wholesome cozy place I would definitely recommend. The lodge is so comforting and so clean. The staff are so welcoming and very nice."
The Winwood Condominiums
10/10 Excellent
"Clean room with nice couch plus kitchenette. Enjoyed setting on patio. Great location, easy walk into town with several restaurants."
Eastwind Windham
10/10 Excellent
"The staff was friendly and the room was clean and comfortable. Would love to come back again!"
Jimmy OConnors Windham Mountain Inn
8/10 Good
"This place is definitely dated but it was clean and the beds were comfortable. Chose to stay here when riding into tue area on the bike becasue of it had a detached restaurant/bar which makes dinner easier. Food was ok and bar was cool."