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Check availability on Windham Romantic Hotels

Tonight
21 Feb - 22 Feb
Tomorrow
22 Feb - 23 Feb
Next weekend
27 Feb - 1 Mar
In two weeks
6 Mar - 8 Mar

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, (42 reviews)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
The price is AED 347
AED 573 total
includes taxes & fees
22 Feb - 23 Feb
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, (56 reviews)
"Nice place and great little town "
United States
PAUL V.
The price is AED 496
AED 817 total
includes taxes & fees
1 Mar - 2 Mar
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior

Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club
3.0 star property
Windham
8.6 out of 10, Excellent, (350 reviews)
"convenient nice and clean residence with kitchen and market nearby."
United States
Jatin
The price is AED 731
AED 789 total
includes taxes & fees
22 Feb - 23 Feb
Winwood Condominiums by Windham Mountain Club
Dinner served

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (870 reviews)
"Great location, very nice common rooms, friendly staff"
United States
Benjamin John
The price is AED 516
AED 637 total
includes taxes & fees
16 Mar - 17 Mar
Hunter Lodge, a Bluebird by Lark
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, (156 reviews)
"Diane was a very gracious host of her lovely BnB! My privacy was well respected and check in/out was easy as pie! Thank you!"
United States
Andrew
The price is AED 731
AED 819 total
includes taxes & fees
22 Feb - 23 Feb
Morning Glory B n B Woodstock NY
Interior detail

Urban Cowboy Lodge

Urban Cowboy Lodge
5.0 star property
Big Indian
9.4 out of 10, Exceptional, (205 reviews)
"Fantastic stay. Only regret was it wasn’t longer! Staff is wonderful and the property was beautiful. Looking forward to our next visit. "
United States
Nate
The price is AED 426
AED 478 total
includes taxes & fees
1 Mar - 2 Mar
Urban Cowboy Lodge
Terrace/patio

Sauna Belleayre Cozy Cabin

Sauna Belleayre Cozy Cabin
Fleischmanns
9.6 out of 10, Exceptional, (124 reviews)
"Excellent stay! Very clean with everything we needed. Loved the sauna! Thank you for an excellent weekend stay."
United States
Christine S.
The price is AED 371
AED 792 total
includes taxes & fees
8 Mar - 9 Mar
Sauna Belleayre Cozy Cabin
Interior

West Kill Barnhouse: Ski, Work & Unwind

West Kill Barnhouse: Ski, Work & Unwind
West Kill
10.0 out of 10, Exceptional, (16 reviews)
"Great stay"
United States
Vijay S.
The price is AED 386
AED 1,349 total
includes taxes & fees
23 Feb - 24 Feb
West Kill Barnhouse: Ski, Work & Unwind
Exterior

Margaretville Mtn Inn B&B and Village Suites

Margaretville Mtn Inn B&B and Village Suites
3.0 star property
Margaretville
8.4 out of 10, Very Good, (211 reviews)
"Staff friendly, breakfast was very good- loved the dining presentation Hot tub was fun. The bed in the Lavender room was really comfortable."
United States
MARK
The price is AED 533
AED 623 total
includes taxes & fees
23 Feb - 24 Feb
Margaretville Mtn Inn B&B and Village Suites
Dining

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Lanesville
9.8 out of 10, Exceptional, (17 reviews)
"Best gateway "
United States
Michael D.
The price is AED 673
AED 1,791 total
includes taxes & fees
22 Feb - 23 Feb
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
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

Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

10/10 Excellent
"Great staff "
Sara 2-night trip
Posted 8 days ago
Winwood Condominiums by Windham Mountain Club
Albergo Allegria Hotel & Breakfast Restaurant

Albergo Allegria Hotel & Breakfast Restaurant

10/10 Excellent
"Lovely hotel and a friendly welcome by the owners. Some small issues arose which we were not affected by, but we were always kept informed. Sadly, we couldn't enjoy the breakfast due to a bereavement in the family but am looking forward to it on our next visit. Thank you and here's hoping to come back soon. "
Michele 2-night trip
Posted 3 weeks ago
Albergo Allegria Hotel & Breakfast Restaurant

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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 Catskill State Park. 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 Catskill State Park.
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.