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 from CA $192

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Check availability on Windham Romantic Hotels

Tonight
Sep 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Windham romantic hotels

A log cabin with a deck, outdoor seating, and a view of a forest.
A wooden covered bridge in a forested area with a paved path leading to it.
A modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.
A cozy cabin interior with a stone fireplace, wooden walls, a dining area with a red and black checkered tablecloth, and a television mounted above the fireplace.

1. Hotel Vienna

Hotel Vienna
Windham
United States
john
CA $163
CA $200 total
includes taxes & fees
Oct 1 - Oct 2
Hotel Vienna
A wooden cabin with a triangular roof, a wooden door, and a bench outside.
A triangular wooden room with a bed and pillows, a window, and a view of a forested hill.
A bar area with wooden beams, a bar counter, and four bar stools.
A round wooden table with a hanging light fixture, surrounded by four stools, set against a backdrop of a large window with a view of trees and a wooden deck.

2. Eastwind Windham

Eastwind Windham
Windham
United States
Sharon
CA $342
CA $412 total
includes taxes & fees
Sep 24 - Sep 25
Eastwind Windham
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.
A room with two blue armchairs, a small round table, a lamp, and a large window with curtains.
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.
Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.

3. Wylder Hotel Windham

Wylder Hotel Windham
Windham
United States
Yousung
CA $386
CA $488 total
includes taxes & fees
Sep 24 - Sep 25
Wylder Hotel Windham
A two-story building with large windows and a storefront.
A house with a snow-covered roof, surrounded by snow-laden trees and a mountainous backdrop.
A snow-covered tractor in a snowy landscape with trees.
A small, cozy room with a bed, a table with plates, a microwave, and a shelf with mugs.

4. 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.
CA $108
CA $192 total
includes taxes & fees
Sep 24 - Sep 25
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
A two-story building with large windows and a storefront.
A residential area with snow-covered houses and a Christmas tree with lights.
A snow-covered tree with bare branches, a building with a blue facade, and a clear blue sky.
A kitchen with wooden cabinets, stainless steel appliances, a red lantern, and a fruit bowl on the counter.

5. 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
David
CA $225
CA $364 total
includes taxes & fees
Sep 29 - Sep 30
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A spacious living room with a stone fireplace, wooden staircase, and modern furniture.
A modern living room with a stone fireplace, a comfortable sofa, and a television mounted on the wall.
A bedroom with a wooden ceiling, a stone wall, a bed, and a view of a hot tub.
A spacious living area with a wooden staircase, a stone fireplace, and a cozy seating arrangement.

6. LUXURY DUPLEX SUITE WITH JACUZZI

LUXURY DUPLEX SUITE WITH JACUZZI
Windham
CA $264
CA $339 total
includes taxes & fees
Sep 24 - Sep 25
LUXURY DUPLEX SUITE WITH JACUZZI
A fire pit with two chairs in a backyard.
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a dining table with four chairs.
A two-story house with a porch, a garage, and a driveway.
A bedroom with a wooden bed, a nightstand, a window with curtains, and a view of trees outside.

7. NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM

NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM
Windham
CA $490
CA $876 total
includes taxes & fees
Sep 24 - Sep 25
NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM
A cozy living room with wooden walls, a stone fireplace, and a television.
A snowy landscape with a wooden deck and a house in the background.
A kitchen with green cabinets, a stainless steel refrigerator, a microwave, a coffee maker, and a stove.
A wooden interior with a dining table and chairs, a kitchen area with a countertop, and a large window providing natural light.

8. Beautiful Windham Chalet 2 minutes to Town and the Mountain

Beautiful Windham Chalet 2 minutes to Town and the Mountain
Windham
United States
John K.
CA $582
CA $965 total
includes taxes & fees
Sep 28 - Sep 29
Beautiful Windham Chalet 2 minutes to Town and the Mountain
A kitchen with green cabinets, a stainless steel stove, and a microwave.
A modern kitchen with green cabinets, a microwave, stove, and a wooden door.
A living room with a brick fireplace, a wooden door leading outside, a sofa, and a cowhide rug.
A bedroom with a large bed, wooden wardrobe, and a television on the wall.

9. NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
Windham
CA $220
CA $283 total
includes taxes & fees
Sep 28 - Sep 29
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
A bedroom with a large bed, a bedside table, a TV mounted on the wall, and a window with curtains.
A dining area with a table and four chairs, a window with curtains, and a ceiling light fixture.
A modern living room with a brick fireplace, leather sofa, and a large fur rug.

10. NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham
Windham
United States
Evelyn
CA $230
CA $297 total
includes taxes & fees
Oct 7 - Oct 8
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham
View all properties

Top Windham Hotel Reviews

The Winwood Condominiums

The Winwood Condominiums

10/10 Excellent
"I came here thirty years ago. And I came here thirty years later, and it's still run by a wonderful proprietor and it's a beautiful place to unwind, and enjoy breakfast in the morning will be a wonderful host if she's not busy. That is taking care of this amazing place. I very much enjoyed my stay"
Dorothy 2-night trip
Posted 12 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 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.

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