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

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

Tonight
14 Aug - 15 Aug
Tomorrow
15 Aug - 16 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Our top choices for Windham romantic hotels

Exterior
Property grounds
Property grounds
Interior

1. 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
United States
Ahmad O.
AED 314
AED 537 total
includes taxes & fees
16 Aug - 17 Aug
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Exterior
Coffee/tea maker, fridge, microwave, oven
Interior
Property grounds

2. 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
United States
Michael C.
AED 477
AED 817 total
includes taxes & fees
16 Aug - 17 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Smart TV, books, stereo, computer monitors
2 bedrooms, desk, iron/ironing board, WiFi (free)
Property grounds
Outdoor dining

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

Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Hunter
United States
Jim D.
AED 804
AED 1,666 total
includes taxes & fees
24 Aug - 25 Aug
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Interior
Interior
Dining
Outdoor dining

4. West Kill Barnhouse: Ski, Work & Unwind

West Kill Barnhouse: Ski, Work & Unwind
West Kill
United States
Vijay S.
AED 459
AED 1,476 total
includes taxes & fees
17 Aug - 18 Aug
West Kill Barnhouse: Ski, Work & Unwind
Property grounds
Coffee/tea maker, fridge, microwave, oven
Exterior
Flat-screen TV

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

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Maplecrest
United States
Yichen
AED 1,319
AED 2,083 total
includes taxes & fees
16 Aug - 17 Aug
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Interior
Interior
Property grounds
Interior

6. Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street

Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street
West Kill
United States
Timothy M.
AED 625
AED 1,635 total
includes taxes & fees
16 Aug - 17 Aug
Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street
Dining
Smart TV, fireplace, books
2 bedrooms, desk, travel crib, WiFi
Property grounds

7. Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Lanesville
United States
Holly
AED 567
AED 1,638 total
includes taxes & fees
19 Aug - 20 Aug
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Property grounds
Smart TV, fireplace, Netflix, Hulu
Exterior
Smart TV, fireplace, Netflix, Hulu

8. QUINN HOLLOW - Hunter Mountain Ski Cabin, Hot Tub

QUINN HOLLOW - Hunter Mountain Ski Cabin, Hot Tub
Hunter
United States
Liz B.
AED 1,028
AED 2,178 total
includes taxes & fees
2 Sep - 3 Sep
QUINN HOLLOW - Hunter Mountain Ski Cabin, Hot Tub
Sauna
Property grounds
Interior
Smart TV, fireplace, table tennis, music library

9. Mountain house with Scandinavian BBQ hut and Hot tub

Mountain house with Scandinavian BBQ hut and Hot tub
Jewett
United States
Despina M.
AED 1,488
AED 2,582 total
includes taxes & fees
23 Aug - 24 Aug
Mountain house with Scandinavian BBQ hut and Hot tub
Terrace/patio
Interior
Property grounds
Coffee/tea maker, fridge, microwave, oven

10. Sauna Belleayre Cozy Cabin

Sauna Belleayre Cozy Cabin
Fleischmanns
United States
Jordan W.
AED 466
AED 933 total
includes taxes & fees
26 Aug - 27 Aug
Sauna Belleayre Cozy Cabin
View all properties

Top Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

8/10 Good
"The only thing I didn't like was the pool was small and the granola they had out was stale for breakfast. Place is very nice and clean."
John 3-night trip
Posted 4 hours ago
Hotel Vienna
The Winwood Condominiums

The Winwood Condominiums

10/10 Excellent
"Very clean property....helpful staff ...lovely setting for the outdoor pool."
kathleen 1-night trip
Posted 11 days ago
The Winwood Condominiums

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.

Explore a world of travel with Expedia