Hotels in Windham
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Aug 17 - Aug 18Tomorrow
Aug 18 - Aug 19This weekend
Aug 21 - Aug 23Next weekend
Aug 28 - Aug 30Top 5 hotels in Windham at a glance
- Hotel Vienna — 3-star hotel in Windham. Guest rating: 9.4/10 — Exceptional.
- Jimmy OConnors Windham Mountain Inn — Located in Windham. Guest rating: 8.6/10 — Excellent.
- The Winwood Condominiums — 3-star hotel in Windham. Guest rating: 8.8/10 — Excellent.
- Eastwind Windham — 3.5-star hotel in Windham. Guest rating: 9.2/10 — Wonderful.
- Cave Mountain Motel — 2.5-star hotel in Windham. Guest rating: 9.4/10 — Exceptional.
Where to stay in Windham?
Jimmy OConnors Windham Mountain Inn
Jimmy OConnors Windham Mountain InnWindham
$122
$131 total
includes taxes & fees
Aug 18 - Aug 19
The Winwood Condominiums
The Winwood CondominiumsWindham
$185
$200 total
includes taxes & fees
Aug 18 - Aug 19
Eastwind Windham
Eastwind WindhamWindham
$201
$246 total
includes taxes & fees
Aug 18 - Aug 19
Cave Mountain Motel
Cave Mountain MotelWindham
$139
$150 total
includes taxes & fees
Aug 18 - Aug 19
Antique Rose Inn Windham
Antique Rose Inn WindhamWindham
$135
$146 total
includes taxes & fees
Aug 18 - Aug 19
Wylder Hotel Windham
Wylder Hotel WindhamWindham
$220
$288 total
includes taxes & fees
Aug 18 - Aug 19
Albergo Allegria Hotel
Albergo Allegria HotelWindham
$174
$188 total
includes taxes & fees
Aug 18 - Aug 19
The Haüs Windham
The Haüs WindhamWindham
$209
$225 total
includes taxes & fees
Aug 19 - Aug 20
'the Mountain House:' Windham Retreat w/ Hot Tub!
'the Mountain House:' Windham Retreat w/ Hot Tub!Windham
$426
$790 total
includes taxes & fees
Aug 23 - Aug 24
Hunter Lodge, a Bluebird by Lark
Hunter Lodge, a Bluebird by LarkHunter
$127
$158 total
includes taxes & fees
Aug 31 - Sep 1
Mountain Treasure B&B
Mountain Treasure B&BMaplecrest
$146
$158 total
includes taxes & fees
Aug 24 - Aug 25
Moore's Motel
Moore's MotelPrattsville
$120
$130 total
includes taxes & fees
Aug 18 - Aug 19
The Wheelhouse Inn
The Wheelhouse InnPine Hill
$170
$190 total
includes taxes & fees
Aug 28 - Aug 29
The Perch Hotel
The Perch HotelEast Windham
$162
$175 total
includes taxes & fees
Aug 20 - Aug 21
The Colonial Motel
The Colonial MotelGrand Gorge
$99
$109 total
includes taxes & fees
Aug 18 - Aug 19
Hotel Mountain Brook
Hotel Mountain BrookTannersville
$179
$193 total
includes taxes & fees
Sep 8 - Sep 9
Kaatskill Mountain Club & Condos by Vail Resorts
Kaatskill Mountain Club & Condos by Vail ResortsHunter
$199
$236 total
includes taxes & fees
Sep 15 - Sep 16
Black Bear Lodge
Black Bear LodgePrattsville
$149
$161 total
includes taxes & fees
Aug 18 - Aug 19
Go beyond your typical stay in Windham
Pet friendly
Apartment
Family friendly
Cottage
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.
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.
Ashland Park
Ashland Park is 4.4 mi (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
Emerson Resort & Spa
10/10 Excellent
"Staff was amazing especially at the restaurant which was right next to our lodge never left the property in 4 days that we stayed there other guests were very friendly and everyone seemed just to want to relax would definitely go back"
Wylder Hotel Windham
10/10 Excellent
"This is the second year I come to Wylder hotel with my family and I am going to make it an annual visit 😍 PS we visit in the summer ❤️ We love it here in the summer! The property is beautiful located in the heart of Windham, NY. Anything you may need is 2-5 mins walk or drive from the hotel. The pool is heated (85 degrees). The restaurant is ahhhhazing. The bakery is delicious. There are so many places around the property where you can just sit, relax, sip coffee or beer, breathe in fresh air. The views are breathtaking. If you are feeling wild you can take a dip in the river. The hotel rooms are ginormous, prob can fit 2 more beds. This hotel is super pet friendly 😍 our pup has been here twice with us now 😊 Staff is professional, kind and always helpful. I LOVE Wylder hotel ❤️ highly recommend."
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
10/10 Excellent
"This is a great getaway trip. It was relaxing and very enjoyable. The place was beautiful and everything was perfectly set up. From easy check in to easy check out. I would recommend and definitely come back!"
AutoCamp Catskills
10/10 Excellent
"I had a great experience at AutoCamp! The property was beautiful, clean, and very peaceful. The staff was friendly and welcoming, and everything was well maintained. I also really loved how pet-friendly it is, which made the experience even better. It was such a relaxing getaway and a great way to enjoy the outdoors while still being comfortable. I would definitely recommend AutoCamp and would love to come back again!"
Urban Cowboy Lodge
8/10 Good
"Room has unique personality, however the room is too small for what I paid for. And we've been told the room will be cleaned daily, never happened. The overall experience is tranquil weekend getaway."
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."
The Winwood Condominiums
10/10 Excellent
"Very clean property....helpful staff ...lovely setting for the outdoor pool."
Cave Mountain Motel
10/10 Excellent
"Wonderful place to stay. I will definitely go back."