Find Romantic Hotels in Windham, NY

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Check availability on Windham Romantic Hotels

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top 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, (40)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
The price is SAR 321
SAR 549 total
includes taxes & fees
8 Dec - 9 Dec
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Seasonal outdoor pool
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

3.0 star property
Windham
8.8 out of 10, Excellent, (344)
"convenient nice and clean residence with kitchen and market nearby."
United States
Jatin
The price is SAR 672
SAR 726 total
includes taxes & fees
8 Dec - 9 Dec
Winwood Condominiums by Windham Mountain Club
Property grounds
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, (54)
"Check in & checkout and communication super easy. Location is excellent. A/C and hot water great. For 4 guys on a 2 day golf trip it worked fine. "
United States
david d.
The price is SAR 540
SAR 867 total
includes taxes & fees
14 Dec - 15 Dec
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Lobby sitting area
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3.0 star property
Hunter
9.2 out of 10, Wonderful, (818)
"Wonderful views, location, and accommodations. I would gladly return to Hunter Lodge"
United States
Russel
The price is SAR 561
SAR 687 total
includes taxes & fees
18 Dec - 19 Dec
Hunter Lodge, a Bluebird by Lark
Indoor wedding
Margaretville Mtn Inn B&B and Village Suites

Margaretville Mtn Inn B&B and Village Suites

3.0 star property
Margaretville
8.2 out of 10, Very Good, (206)
"Our stay at the Margaretville Mtn Inn was fantastic. The room was beautiful and very clean. The breakfast that was served was wholesome and delicious. I would definitely stay there again."
United States
Neal
The price is SAR 507
SAR 595 total
includes taxes & fees
4 Jan - 5 January 2026
Margaretville Mtn Inn B&B and Village Suites
Restaurant
Urban Cowboy Lodge

Urban Cowboy Lodge

5.0 star property
Big Indian
9.2 out of 10, Wonderful, (187)
" Didn’t get the room shown on Expedia website so we were disappointed in that. Overall nice place and really enjoyed our stay. "
United States
Stuart
The price is SAR 844
SAR 946 total
includes taxes & fees
18 Dec - 19 Dec
Urban Cowboy Lodge
Property grounds
Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

Woodstock
10.0 out of 10, Exceptional, (261)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
The price is SAR 747
SAR 1,454 total
includes taxes & fees
13 Dec - 14 Dec
Streamside Cottage Half Mile to Town of Woodstock
Fridge, microwave, oven, stovetop
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Lanesville
9.8 out of 10, Exceptional, (16)
"Simply perfect! This house was clean, fully stocked of all necessities and optimally located for hiking, town hoping, art seeing and brewery bouncing. Would love to come back in the winter for its proximity to Hunter Mountain. Highly recommend!"
United States
Sarah P.
The price is SAR 769
SAR 1,924 total
includes taxes & fees
10 Dec - 11 Dec
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Children's area
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

woodstock
9.0 out of 10, Wonderful, (45)
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. "
United States
Shannon F.
The price is SAR 676
SAR 1,160 total
includes taxes & fees
14 Dec - 15 Dec
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Studio, Private Bathroom, Garden View (Dove house on Tannery br) | View from property
Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY

3.0 star property
Woodstock
8.4 out of 10, Very Good, (155)
"Beautiful historic home. We had a nice stay. "
United States
Anonymous traveler
The price is SAR 709
SAR 794 total
includes taxes & fees
8 Dec - 9 Dec
Morning Glory B n B Woodstock NY
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.
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Top Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Great place for local skiing. Very little local wifi coverage so make sure you have all your check-in details in advance. Nice spot."
Bruce 1-night trip
Posted 7 days ago
Hotel Vienna

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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.