Find Romantic Hotels in Windham, NY

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Check availability on Windham Romantic Hotels

Tonight
Aug 2 - Aug 3
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Aug 3 - Aug 4
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Aug 8 - Aug 10
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Aug 15 - Aug 17

Top Windham Romantic Hotels

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Recommended hotels in Windham

Hotel Vienna
Escape to a serene retreat amidst lush greenery, with a spacious deck perfect for relaxation or entertaining.

Hotel Vienna

2.5 star property
9.4 out of 10, Exceptional, (603)
"Lovely accommodations and setting."
The price is ₩173,822
₩187,728 total
includes taxes & fees
Aug 3 - Aug 4
Hotel Vienna
Cave Mountain Motel
Stunning two-story home with a charming porch and beautifully manicured yard.

Cave Mountain Motel

2.5 star property
9.4 out of 10, Exceptional, (129)
"Beautiful view in The Catskills."
The price is ₩193,136
₩208,587 total
includes taxes & fees
Aug 3 - Aug 4
Cave Mountain Motel
Antique Rose Inn Windham
Stunning two-story house with a charming porch and tower, surrounded by a serene winter landscape.

Antique Rose Inn Windham

3.0 star property
9.0 out of 10, Wonderful, (121)
"We did not expect to share a bathroom. We should of done our homework on the place. Its a lovely place to stay. Owner is very friendly, breakfast was accommodating to our wishes."
The price is ₩187,578
₩202,584 total
includes taxes & fees
Aug 4 - Aug 5
Antique Rose Inn Windham
Albergo Allegria Hotel & Breakfast Restaurant
Enjoy a meal at the dining table, with a view of the surrounding landscape through the large window.

Albergo Allegria Hotel & Breakfast Restaurant

3.5 star property
9.6 out of 10, Exceptional, (265)
"Friendly, clean, beautiful setting"
The price is ₩201,640
₩217,786 total
includes taxes & fees
Aug 3 - Aug 4
Albergo Allegria Hotel & Breakfast Restaurant
Eastwind Windham
Two-story house with a front entrance, wooden deck, and potted plants on the steps.

Eastwind Windham

2.0 star property
9.2 out of 10, Wonderful, (57)
"excellent place to stay with great surrounding areas to explore and helpful friendly staff. "
The price is ₩276,685
₩308,518 total
includes taxes & fees
Aug 3 - Aug 4
Eastwind Windham
Winwood Condominiums by Windham Mountain Club
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Winwood Condominiums by Windham Mountain Club

3.0 star property
8.6 out of 10, Excellent, (326)
"Wonderful property "
The price is ₩276,505
₩298,625 total
includes taxes & fees
Aug 3 - Aug 4
Winwood Condominiums by Windham Mountain Club
The Haüs Windham
Cozy attic bedroom with a large bathroom, bathtub, and comfortable bed.

The Haüs Windham

2.0 star property
8.8 out of 10, Excellent, (8)
"Great place nice and clean"
The price is ₩258,483
₩279,161 total
includes taxes & fees
Aug 4 - Aug 5
The Haüs Windham
Beds on Clouds
Stroll through lush gardens surrounded by classic columns and vibrant flowers.

Beds on Clouds

3.0 star property
7.4 out of 10, Good, (67)
"Great spot for a weekend getaway"
The price is ₩238,086
₩257,122 total
includes taxes & fees
Aug 4 - Aug 5
Beds on Clouds
Wylder Hotel Windham
Relax in this stylish room with two armchairs and a round table, offering a view of the outdoors through the large window.

Wylder Hotel Windham

3.5 star property
8.6 out of 10, Excellent, (65)
"We LOVED staying at Wylder. The staff was super friendly and helpful. Our room was comfortable, views were amazing and we really enjoyed the amenities. Highly recommend! "
The price is ₩336,515
₩432,911 total
includes taxes & fees
Aug 31 - Sep 1
Wylder Hotel Windham
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

Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

10/10 Excellent
"Wonderful property "
Irina 1-night trip
Posted 5 days ago
Winwood Condominiums by Windham Mountain Club

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.
How many romantic hotels can we expect to find in Windham?
Expedia has 14 romantic Windham hotels for you both to enjoy.
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.