Find Romantic Hotels in Windham, NY

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Check availability on Windham Romantic Hotels

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Top Windham Romantic Hotels

Hunter Lodge, a Bluebird by Lark
Lobby sitting area

Hunter Lodge, a Bluebird by Lark

3.0 star property
9.2 out of 10, Wonderful, (773)
"Amazing place for a quality weekend."
The price is AED 451
AED 567 total
includes taxes & fees
2 Nov - 3 Nov
Hunter Lodge, a Bluebird by Lark
Margaretville Mtn Inn B&B and Village Suites
Indoor wedding

Margaretville Mtn Inn B&B and Village Suites

3.0 star property
8.4 out of 10, Very Good, (202)
"Beautiful remote location. A throw back in time!! And the hot tub was a nice touch! Host was very laid back and kind. Food was yummy!!"
The price is AED 533
AED 606 total
includes taxes & fees
6 Oct - 7 Oct
Margaretville Mtn Inn B&B and Village Suites
Urban Cowboy Lodge
Restaurant

Urban Cowboy Lodge

5.0 star property
9.2 out of 10, Wonderful, (168)
"Just the whole experience was amazing. We enjoyed it so much (my daughter and I) that we want to return for Mother's Day. "
The price is AED 655
AED 733 total
includes taxes & fees
5 Oct - 6 Oct
Urban Cowboy Lodge
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Exterior

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

9.2 out of 10, Wonderful, (38)
"Great place for an incredible price. We would definitely stay here again."
The price is AED 264
AED 484 total
includes taxes & fees
5 Oct - 6 Oct
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Property grounds

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

9.0 out of 10, Wonderful, (51)
"Great communication with host Nice spacious clean apartment. Good location "
The price is AED 404
AED 726 total
includes taxes & fees
2 Nov - 3 Nov
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Crystal Brook Resort & Mountain Brauhaus
Seasonal outdoor pool

Crystal Brook Resort & Mountain Brauhaus

2.5 star property
9.0 out of 10, Wonderful, (97)
"We loved our stay at Crystal Brook…it is like The Land That Time Forgot! If you’re looking for comfort, delicious food and friendly owners and staff, you’ll love it! "
Crystal Brook Resort & Mountain Brauhaus
Sauna Belleayre Cozy Cabin
Property grounds

Sauna Belleayre Cozy Cabin

9.6 out of 10, Exceptional, (119)
"Enjoyed everything and every moment of our short stay,"
The price is AED 463
AED 929 total
includes taxes & fees
5 Oct - 6 Oct
Sauna Belleayre Cozy Cabin
Morning Glory B n B Woodstock NY
Studio, Private Bathroom, Garden View (Dove house on Tannery br) | View from property

Morning Glory B n B Woodstock NY

3.0 star property
8.6 out of 10, Excellent, (154)
"Great owner. Friendly, quaint and ver"
The price is AED 841
AED 942 total
includes taxes & fees
6 Oct - 7 Oct
Morning Glory B n B Woodstock NY
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Fridge, microwave, oven, stovetop

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

9.8 out of 10, Exceptional, (14)
"We had a great stay, the place was beautiful and so many thoughtful amenities!"
The price is AED 753
AED 1,790 total
includes taxes & fees
3 Nov - 4 Nov
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Belleayre Grandhouse 6 bedrooms sleep 15 w/hot tub, sauna, game lounge.
Outdoor spa tub

Belleayre Grandhouse 6 bedrooms sleep 15 w/hot tub, sauna, game lounge.

9.6 out of 10, Exceptional, (37)
"A great place to stay with a big group, had a great experience "
Belleayre Grandhouse 6 bedrooms sleep 15 w/hot tub, sauna, game lounge.
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

Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

10/10 Excellent
"The pool was closed for the season but looked like it was very nice. It is across the street so wouldn't be the easiest to access. There was a game room with a few arcade games, a pool table, foosball, and ping pong. Maybe consider a coin machine in the room? The condo was beautiful with a gorgeous view. Would definitely stay again! "
Ashley 1-night trip
Posted 4 days ago
Winwood Condominiums by Windham Mountain Club

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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.