Find Romantic Hotels in Windham, NY

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Our top choices for Windham romantic hotels

1. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (914 reviews)
"Clean room and helpful staff, good location."
United States
Hongtao
The price is AED 413
AED 510 total
includes taxes & fees
22 Nov - 23 Nov
Hotel Vienna

2. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (139 reviews)
"Room super clean and beautiful property!"
United States
Daniela
The price is AED 684
AED 922 total
includes taxes & fees
23 Nov - 24 Nov
Wylder Hotel Windham

3. 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, (46 reviews)
"Great, highly recommend"
United States
Rebecca
The price is AED 275
AED 464 total
includes taxes & fees
15 Nov - 16 Nov
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

4. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (123 reviews)
"Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay."
United States
Danica
The price is AED 834
AED 1,009 total
includes taxes & fees
14 Dec - 15 Dec
Eastwind Windham

5. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.0 out of 10, Very good, (40 reviews)
"Easy check in, nice layout of the apt, comfortable bed, nice to have a kitchen. Nearby lots of restaurants and mountain access. "
United States
Erica
The price is AED 536
AED 1,129 total
includes taxes & fees
16 Nov - 17 Nov
The Haüs Windham

6. 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
8.8 out of 10, Excellent, (66 reviews)
"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."
United States
April
The price is AED 404
AED 690 total
includes taxes & fees
16 Nov - 17 Nov
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

1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mountain
Windham
7.6 out of 10, Good, (5 reviews)
"Excellent accommodations, close to everything you could need. My wife and I had a perfect evening "
United States
Anthony M.
The price is AED 545
AED 676 total
includes taxes & fees
16 Nov - 17 Nov
1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mountain

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

Beautiful Windham Chalet 2 minutes to Town and the Mountain
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Very easy to check in and check out. Very excellent instructions and welcoming atmosphere. "
United States
John K.
The price is AED 1,428
AED 2,320 total
includes taxes & fees
17 Nov - 18 Nov
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

5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn
Windham
The price is AED 1,337
AED 2,256 total
includes taxes & fees
17 Nov - 18 Nov
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

Duplex Suite with Jacuzzi, Steam Shower and Sauna, 3 Min to Windham Mtn
Windham
The price is AED 683
AED 845 total
includes taxes & fees
17 Nov - 18 Nov
Duplex Suite with Jacuzzi, Steam Shower and Sauna, 3 Min to Windham Mtn
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.

Top Windham Hotel Reviews

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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