Search Romantic Hotels in Windham

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Windham Romantic Hotels

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

Top Windham Romantic Hotels

Seasonal outdoor pool
Winwood Condominiums by Windham Mountain Club
Winwood Condominiums by Windham Mountain Club
3.0 star property
8.8 out of 10, Excellent, (342)
"Great location and great property"
United States
Joel
The price is ฿5,491
฿5,931 total
includes taxes & fees
9 Nov - 10 Nov
Winwood Condominiums by Windham Mountain Club
Lobby sitting area
Hunter Lodge, a Bluebird by Lark
Hunter Lodge, a Bluebird by Lark
3.0 star property
9.2 out of 10, Wonderful, (801)
"Nice quiet place, very kind staff."
United States
Bernard
The price is ฿4,584
฿5,653 total
includes taxes & fees
23 Nov - 24 Nov
Hunter Lodge, a Bluebird by Lark
Indoor wedding
Margaretville Mtn Inn B&B and Village Suites
Margaretville Mtn Inn B&B and Village Suites
3.0 star property
8.2 out of 10, Very good, (205)
"Our stay at the Margaretville Mtn Inn was fantastic. The room was beautiful and very clean. The breakfast that was served was wholesome and delicious. I would definitely stay there again."
United States
Neal
The price is ฿4,387
฿5,150 total
includes taxes & fees
9 Nov - 10 Nov
Margaretville Mtn Inn B&B and Village Suites
Studio, Private Bathroom, Garden View (Dove house on Tannery br) | View from property
Morning Glory B n B Woodstock NY
Morning Glory B n B Woodstock NY
3.0 star property
8.4 out of 10, Very good, (155)
"Morning Glory B&B provided everything I needed for a comfortable and pleasant stay. While it isn’t a luxurious property, it covers all the basics well—clean, functional, and welcoming. The location is convenient, a 10 minute walk to the Village Green, with easy access to shopping, dining, and the center of Woodstock’s activity. A solid choice if you’re looking for simplicity, comfort, and proximity rather than frills. "
United States
Adrian
The price is ฿6,141
฿6,878 total
includes taxes & fees
2 Dec - 3 Dec
Morning Glory B n B Woodstock NY
Restaurant
Urban Cowboy Lodge
Urban Cowboy Lodge
5.0 star property
9.2 out of 10, Wonderful, (176)
"Just the whole experience was amazing. We enjoyed it so much (my daughter and I) that we want to return for Mother's Day. "
United States
Brenda
The price is ฿9,066
฿10,154 total
includes taxes & fees
18 Nov - 19 Nov
Urban Cowboy Lodge
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.
View all properties

Top Windham Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Windham?
Are you and your partner looking for a romantic holiday? Our guests also enjoy Windham for its coffee shops, 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 neighbourhood 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, take a look at these details about year-round temperatures in Windham: The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Windham are January, March, December and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Windham?
There's nothing better than wandering around 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 coffee shops, 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 getaway go off without a hitch: 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 centre. If you'd like to venture out around the area, you may want to rent a car for your trip.