Find Romantic Hotels in Windham, NY

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Windham Romantic Hotels

Our top choices for Windham romantic hotels

Exterior

Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club
3.0 star property
Windham
8.6 out of 10, Excellent, (349 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
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

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, (41 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
17 Feb - 18 Feb
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
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, (866 reviews)
"Great location, very nice common rooms, friendly staff"
United States
Benjamin John
The price is AED 514
AED 635 total
includes taxes & fees
16 Mar - 17 Mar
Hunter Lodge, a Bluebird by Lark
Interior detail

Urban Cowboy Lodge

Urban Cowboy Lodge
5.0 star property
Big Indian
9.4 out of 10, Exceptional, (202 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 551
AED 617 total
includes taxes & fees
23 Feb - 24 Feb
Urban Cowboy Lodge
Exterior

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, (210 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)
"This was a beautiful little spot and had everything! We loved our 3 night stay."
United States
Holly
The price is AED 636
AED 1,773 total
includes taxes & fees
17 Feb - 18 Feb
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
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
17 Feb - 18 Feb
Morning Glory B n B Woodstock NY
Terrace/patio

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, (46 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
The price is AED 661
AED 1,152 total
includes taxes & fees
22 Feb - 23 Feb
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
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 658
AED 1,168 total
includes taxes & fees
17 Feb - 18 Feb
Sauna Belleayre Cozy Cabin
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

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now

Top Windham Hotel Reviews

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
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

10/10 Excellent
"Great staff, shuttle to mountain "
Charlie 2-night trip
Posted 3 weeks ago
Winwood Condominiums by Windham Mountain Club

Explore a world of travel with Expedia

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.