The Best Romantic Hotels in Windham, NY from AED 247 in 2026

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Our top choices for Windham romantic hotels

A log cabin with a deck, outdoor seating, and a view of a forest.

1. Hotel Vienna

Windham

Hongtao

AED 510 total

includes taxes & fees

22 Nov - 23 Nov

A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

2. Wylder Hotel Windham

Windham

Daniela

AED 922 total

includes taxes & fees

23 Nov - 24 Nov

A two-story building with large windows and a storefront.

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

Windham

Rebecca

AED 434 total

includes taxes & fees

15 Nov - 16 Nov

A wooden cabin with a triangular roof, a wooden door, and a bench outside.

4. Eastwind Windham

Windham

Danica

AED 1,009 total

includes taxes & fees

14 Dec - 15 Dec

A bedroom with a large window, a bed, and a view of a forest.

5. The Haüs Windham

Windham

Erica

AED 1,129 total

includes taxes & fees

16 Nov - 17 Nov

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

Windham

"The pictures are not accurate. The two full and one twin bed are in one room upstairs, they are not separated as pictures would lead you to believe. Then three twins are in the living room with the couch, next to the dining room table and kitchen. The unit was dusty and not swept clean. There were dead bugs on the floor and party poppers from previous guest. I have never experienced something like this with Expedia, this was a zero star experience honestly."

April

AED 690 total

includes taxes & fees

16 Nov - 17 Nov

A living room with a brick fireplace, leather sofa, and a flat-screen TV.

7. 1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mountain

Windham

Anthony M.

AED 676 total

includes taxes & fees

16 Nov - 17 Nov

A cozy living room with wooden walls, a stone fireplace, and a television.

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

Windham

John K.

AED 2,368 total

includes taxes & fees

2 Dec - 3 Dec

A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

9. 5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn

Windham

AED 2,256 total

includes taxes & fees

16 Nov - 17 Nov

A spacious living room with a stone fireplace, wooden staircase, and modern furniture.

10. Duplex Suite with Jacuzzi, Steam Shower and Sauna, 3 Min to Windham Mtn

Windham

AED 845 total

includes taxes & fees

16 Nov - 17 Nov

View all properties

Top Windham Hotel Reviews

Hotel Vienna

Windham

10/10 Excellent

michael

Eastwind Windham

Windham

10/10 Excellent

Danica

A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

Shandaken Inn

Shandaken

10/10 Excellent

Anonymous traveler

A cabin with a triangular window, wooden walls, and a bed with pillows.

Gather Greene

Coxsackie

10/10 Excellent

This place was magical. Rooms were clean. Same amenities as a hotel. Blow dryer available! Mini fridge and a sheet for blinds if you need. The snow falling in the early morning was the highlight of the cabin stay. Very beautiful! There were two campfires and snores every night from 5-1pm. Very cute! Cabins are about 50-100ft from parking so be prepared to walk in snow after parking your care. You can get closer to a loading zone to load things into and out of cabins if needed though. String...

Liana

A white house with a green door, black trim, and a porch with a lantern.

Twin Gables of Woodstock

Woodstock

10/10 Excellent

One of the coolest and most accommodating places I have ever stayed. If you are coming to Woodstock are even thinking about it this is the place for you. All the rooms are unique, they are super clean and look exactly like they do online. The owner is amazing and she will point you in the right direction for whatever you are looking to do in town. Seriously cannot recommend enough and can’t wait to come back.

Noah

A room with a view of a landscape through a window, a chair, a table with a laptop, and a bed with books on it.

The Perch Hotel

East Windham

10/10 Excellent

A Hidden Gem with Million-Dollar Views! We had such a magical stay at The Perch Hotel in East Windham! The view alone is worth the trip — on a clear day, you can see FIVE states from the property. Yes, five! It’s absolutely breathtaking and made for the perfect backdrop to relax and soak in the Catskills air. The vibe of the hotel is something special — a perfect blend of modern comfort and mid-century charm that instantly transported me back to the golden era of Catskill tourism. It’s stylish...

Emmi

A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

10/10 Excellent

Leslie

A park with Adirondack chairs and a table, surrounded by trees.

Mountain Treasure B&B

Maplecrest

10/10 Excellent

Alina

A multi-story building with outdoor seating and a stone-paved patio.

Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

10/10 Excellent

Joseph

A rustic interior with a stone fireplace, wooden beams, and a chandelier.

Urban Cowboy Lodge

Big Indian

10/10 Excellent

Carolena

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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Find Romantic Hotels in Windham, NY

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windham romantic hotels

1. Hotel Vienna

2. Wylder Hotel Windham

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

4. Eastwind Windham

5. The Haüs Windham

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

7. 1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mountain

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

9. 5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn

10. Duplex Suite with Jacuzzi, Steam Shower and Sauna, 3 Min to Windham Mtn

Top Windham Hotel Reviews

Hotel Vienna

10/10 Excellent

Frequently Asked Questions

Searching for romantic hotels in Windham?

When is the best time of year for a romantic getaway to Windham?

What is there to do in Windham?

What’s the best way to get to Windham and around town during my romantic getaway?

Explore a world of travel with Expedia