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 $165

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Check availability on Windham Romantic Hotels

Tonight
Aug 6 - Aug 7
Tomorrow
Aug 7 - Aug 8
This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

Our top choices for Windham romantic hotels

1. Hotel Vienna

Hotel Vienna
Windham
United States
Laszlo
CA $183
CA $222 total
includes taxes & fees
Aug 11 - Aug 12
Hotel Vienna

2. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
United States
Amy
CA $153
CA $165 total
includes taxes & fees
Aug 18 - Aug 19
Jimmy OConnors Windham Mountain Inn

3. The Winwood Condominiums

The Winwood Condominiums
Windham
United States
Nicoletta
CA $233
CA $252 total
includes taxes & fees
Aug 9 - Aug 10
The Winwood Condominiums

4. Eastwind Windham

Eastwind Windham
Windham
United States
Marta
CA $253
CA $313 total
includes taxes & fees
Aug 9 - Aug 10
Eastwind Windham

5. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
Hunter
United States
Yessenia
CA $166
CA $209 total
includes taxes & fees
Sep 1 - Sep 2
Hunter Lodge, a Bluebird by Lark

6. Cave Mountain Motel

Cave Mountain Motel
Windham
United States
Sarah
CA $195
CA $210 total
includes taxes & fees
Aug 9 - Aug 10
Cave Mountain Motel

7. Albergo Allegria Hotel

Albergo Allegria Hotel
Windham
United States
Roy
CA $243
CA $263 total
includes taxes & fees
Aug 9 - Aug 10
Albergo Allegria Hotel

8. Wylder Hotel Windham

Wylder Hotel Windham
Windham
United States
Linda
CA $281
CA $374 total
includes taxes & fees
Aug 11 - Aug 12
Wylder Hotel Windham

9. Antique Rose Inn Windham

Antique Rose Inn Windham
Windham
United States
David
CA $189
CA $204 total
includes taxes & fees
Aug 10 - Aug 11
Antique Rose Inn Windham

10. Mountain Treasure B&B

Mountain Treasure B&B
Maplecrest
United States
cynthia
CA $205
CA $221 total
includes taxes & fees
Aug 10 - Aug 11
Mountain Treasure B&B
View all properties

Top Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Fresh croissants for breakfast"
NANCY 2-night trip
Posted 9 hours ago
Hotel Vienna
The Winwood Condominiums

The Winwood Condominiums

10/10 Excellent
"Very clean property....helpful staff ...lovely setting for the outdoor pool."
kathleen 1-night trip
Posted 2 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 Catskill State Park. 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 Catskill State Park.
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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