A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

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Check availability on Windham Romantic Hotels

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

Our top choices for Windham romantic hotels

Exterior

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
9.2 out of 10, Wonderful, (45 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
The price is AED 298
AED 520 total
includes taxes & fees
1 Jul - 2 Jul
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Exterior

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (60 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is AED 514
AED 861 total
includes taxes & fees
8 Jul - 9 Jul
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Property grounds

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Maplecrest
10.0 out of 10, Exceptional, (22 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
The price is AED 1,319
AED 2,079 total
includes taxes & fees
1 Jul - 2 Jul
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Dining

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Lanesville
9.8 out of 10, Exceptional, (18 reviews)
"This was a beautiful little spot and had everything! We loved our 3 night stay."
United States
Holly
The price is AED 946
AED 2,104 total
includes taxes & fees
1 Jul - 2 Jul
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Terrace/patio

Sauna Belleayre Cozy Cabin

Sauna Belleayre Cozy Cabin
Fleischmanns
9.6 out of 10, Exceptional, (131 reviews)
"Very cozy and comfortable, super close toBelleayre. We enjoyed the sauna after a day of skiing. Thank you for an amazing stay! "
United States
Taku T.
The price is AED 502
AED 981 total
includes taxes & fees
13 Jul - 14 Jul
Sauna Belleayre Cozy Cabin
Smart TV, books, stereo, computer monitors

Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!

Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Hunter
9.8 out of 10, Exceptional, (18 reviews)
"Nice home, spacious, and conveniently located minutes from Hunter. I would stay here again. "
United States
Jim D.
The price is AED 731
AED 1,563 total
includes taxes & fees
8 Jul - 9 Jul
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Property grounds

QUINN HOLLOW - Hunter Mountain Ski Cabin, Hot Tub

QUINN HOLLOW - Hunter Mountain Ski Cabin, Hot Tub
Hunter
9.8 out of 10, Exceptional, (26 reviews)
"Loved the hot tub, location being so close to the mountain, and cozy living room "
United States
Liz B.
The price is AED 1,142
AED 2,285 total
includes taxes & fees
21 Jul - 22 Jul
QUINN HOLLOW - Hunter Mountain Ski Cabin, Hot Tub
Smart TV, fireplace, books

Catskill Mountain Hideaway with Amazing Hunter Mountain Views

Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Hunter
10.0 out of 10, Exceptional, (13 reviews)
"Very clean and comfy place to stay. Communication with owner is quick and easy. Highly recommendations "
United States
ching yi t.
The price is AED 1,319
AED 2,503 total
includes taxes & fees
1 Jul - 2 Jul
Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Sauna

Mountain house with Scandinavian BBQ hut and Hot tub

Mountain house with Scandinavian BBQ hut and Hot tub
Jewett
10.0 out of 10, Exceptional, (72 reviews)
"Beautiful home, comfortable bedding, great amenities, great communication with host, overall lovely property. We loved the jacuzzi, bbq hut & she shed. "
United States
Despina M.
The price is AED 1,469
AED 2,563 total
includes taxes & fees
26 Jul - 27 Jul
Mountain house with Scandinavian BBQ hut and Hot tub
Exterior

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Hunter
10.0 out of 10, Exceptional, (277 reviews)
"Clean and spacious lodge, with fun activities available."
United States
D L.
The price is AED 2,571
AED 4,935 total
includes taxes & fees
28 Jul - 29 Jul
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
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.
View all properties

Top Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Lovely room. Great staff. Very enjoyable stay!"
Hope 2-night trip
Posted 2 days ago
Hotel Vienna
Albergo Allegria Hotel

Albergo Allegria Hotel

10/10 Excellent
"We had an absolutely delightful stay - from the beautifully decorated room, to the comfy porches and sitting room, to the delicious coffee and warm fire pit! We met the loveliest people and our hosts were caring and helpful. We will definitely be returning! This place is a gem!!!"
Daphna 2-night trip
Posted 6 days ago
Albergo Allegria Hotel

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Frequently asked questions

Searching for romantic hotels in Windham?
Are you looking for a romantic getaway? Our guests also enjoy Windham for its coffeehouses, skiing, and mountain views. If you'd like to explore some of the area's notable sights, you might make a stop by Windham Country Club, Windham Mountain Resort, or Windham Vineyards and Winery. If you're interested in staying close to a particular destination, you can sort properties by neighborhood or distance to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Windham?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Windham: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Windham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Windham?
There's nothing better than seeing a new place with your sweetheart, so consider checking out all that Windham has to offer. Couples looking for a little of everything will enjoy Windham for its coffeehouses, skiing, and mountain views. You might think about visiting Windham Country Club, Windham Mountain Resort, or Windham Vineyards and Winery.
What's the best way to get to Windham and around town during my romantic getaway?
This information about transportation options in Windham might help your romantic trip get off to a smooth start: To get to Windham, you can fly into Hudson, NY (HCC-Columbia County), which is the closest major airport, located 27.6 mi (44.4 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.