Find Romantic Hotels in Windham, NY

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Check availability on Windham Romantic Hotels

Top Windham Romantic Hotels

Urban Cowboy Lodge
Restaurant

Urban Cowboy Lodge

5.0 star property
9.2 out of 10, Wonderful, (161)
"The staff here was amazing, had a great one night getaway and I wished we stayed longer! Definitely would come back! Service A plus! Food A plus! Scenery outstanding! Definitely recommend for a good wind down from ones busy day to day."
The price is NT$5,108
NT$5,721 total
includes taxes & fees
Aug 25 - Aug 26
Urban Cowboy Lodge
Hunter Lodge, a Bluebird by Lark
Lobby sitting area

Hunter Lodge, a Bluebird by Lark

3.0 star property
9.2 out of 10, Wonderful, (737)
"Nice quiet place, very kind staff."
The price is NT$4,119
NT$5,099 total
includes taxes & fees
Aug 25 - Aug 26
Hunter Lodge, a Bluebird by Lark
Margaretville Mtn Inn B&B and Village Suites
Indoor wedding

Margaretville Mtn Inn B&B and Village Suites

3.0 star property
8.4 out of 10, Very Good, (200)
"We enjoyed our stay! Very clean and cozy. Delicious breakfast and charming ambiance!"
The price is NT$4,355
NT$4,956 total
includes taxes & fees
Sep 2 - Sep 3
Margaretville Mtn Inn B&B and Village Suites
Winwood Condominiums by Windham Mountain Club
Seasonal outdoor pool

Winwood Condominiums by Windham Mountain Club

3.0 star property
8.6 out of 10, Excellent, (331)
"Wonderful property "
The price is NT$5,977
NT$6,455 total
includes taxes & fees
Aug 21 - Aug 22
Winwood Condominiums by Windham Mountain Club
Crystal Brook Resort & Mountain Brauhaus
Seasonal outdoor pool

Crystal Brook Resort & Mountain Brauhaus

2.5 star property
9.0 out of 10, Wonderful, (94)
"Beautiful property overseen by a lovely person, Wendy was hospitable in every sense of the word; would absolutely love to come back to this amazing retreat in the woods. Also worth mentioning is the amazing waterfall within walking distance of the property. "
The price is NT$6,233
NT$6,732 total
includes taxes & fees
Aug 21 - Aug 22
Crystal Brook Resort & Mountain Brauhaus
Morning Glory B n B Woodstock NY
Studio, Private Bathroom, Garden View (Dove house on Tannery br) | View from property

Morning Glory B n B Woodstock NY

3.0 star property
8.6 out of 10, Excellent, (145)
"We absolutely loved our stay - the white room was clean and lovely. We love the location too - great proximity to Station, movie theater and restaurants."
The price is NT$5,992
NT$6,711 total
includes taxes & fees
Sep 3 - Sep 4
Morning Glory B n B Woodstock NY
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Hotel was very clean, grounds looked great and the owner/manager was constantly waiting on guests. "
Abbie 1-night trip
Posted 4 days ago
Hotel Vienna

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.
What's the best accommodation for a romantic vacation in Windham?
Winwood Inn & Condominiums is a favorite hotel for couples, and features flat-screen TVs and a full-service spa. Another choice for a romantic stay is Hammo's Lodge.
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.