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Check availability on Windham Romantic Hotels

Our top choices for Windham romantic hotels

Exterior

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
9.0 out of 10, Wonderful, (59 reviews)
"Lovely hosts "
United States
Tyler G.
The price is AED 441
AED 762 total
includes taxes & fees
18 May - 19 May
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior

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, (44 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
The price is AED 294
AED 516 total
includes taxes & fees
17 May - 18 May
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Terrace/patio

Sauna Belleayre Cozy Cabin

Sauna Belleayre Cozy Cabin
Fleischmanns
9.6 out of 10, Exceptional, (130 reviews)
"Great stay in a lovely area."
United States
Jordan W.
The price is AED 456
AED 914 total
includes taxes & fees
19 May - 20 May
Sauna Belleayre Cozy Cabin
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (279 reviews)
"The view in the snow was absolutely gorgeous and the size of the accommodations was perfect!"
United States
Abigail Y.
The price is AED 658
AED 1,276 total
includes taxes & fees
5 Jun - 6 Jun
Streamside Cottage Half Mile to Town of Woodstock
Terrace/patio

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
9.0 out of 10, Wonderful, (47 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
The price is AED 661
AED 1,140 total
includes taxes & fees
17 May - 18 May
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Interior

West Kill Barnhouse: Ski, Work & Unwind

West Kill Barnhouse: Ski, Work & Unwind
West Kill
10.0 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Vijay S.
The price is AED 643
AED 1,678 total
includes taxes & fees
16 May - 17 May
West Kill Barnhouse: Ski, Work & Unwind
Property grounds

QUINN HOLLOW - Hunter Mountain Ski Cabin, Hot Tub

QUINN HOLLOW - Hunter Mountain Ski Cabin, Hot Tub
Hunter
9.8 out of 10, Exceptional, (26 reviews)
"Had the best week at Quinn Hollow. Truly the perfect place to relax after days of skiing. Hope to be back!"
United States
Jacqueline G.
The price is AED 918
AED 2,027 total
includes taxes & fees
21 May - 22 May
QUINN HOLLOW - Hunter Mountain Ski Cabin, Hot Tub
Terrace/patio

The Lakefront Chalet - Ski, Ride, Golf, Bike, Hike

The Lakefront Chalet - Ski, Ride, Golf, Bike, Hike
Hunter
10.0 out of 10, Exceptional, (111 reviews)
"The stay was fantastic!! It was a wonderful location and was so nice with the lake access. "
United States
Lydia S.
The price is AED 1,069
AED 3,023 total
includes taxes & fees
21 May - 22 May
The Lakefront Chalet - Ski, Ride, Golf, Bike, Hike
Property grounds

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Maplecrest
10.0 out of 10, Exceptional, (22 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
The price is AED 1,319
AED 2,051 total
includes taxes & fees
21 May - 22 May
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Fridge, microwave, oven, stovetop

Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room

Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room
Hunter
9.6 out of 10, Exceptional, (13 reviews)
"⭐️⭐️⭐️⭐️⭐️ The most important part of any stay is having a great host — and we truly did! Our host was incredibly welcoming, responsive, and thoughtful, which made the entire experience so much smoother and more enjoyable. The property itself was cozy, well-maintained, and perfectly located to explore Hunter, NY. We felt right at home from the moment we arrived and left with wonderful memories. Highly recommend this place to anyone visiting the area!"
United States
Taha
The price is AED 1,175
AED 2,309 total
includes taxes & fees
17 May - 18 May
Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room
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.
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Top Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Very nice."
Marek 2-night trip
Posted 1 month ago
Hotel Vienna

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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.