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Find Romantic Hotels in Windham, NY from CA $204

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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, (60 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is CA $182
CA $311 total
includes taxes & fees
Jun 14 - Jun 15
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, (45 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
The price is CA $119
CA $204 total
includes taxes & fees
Jun 15 - Jun 16
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Combined shower/tub, hair dryer, towels, soap

Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!

Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Hunter
9.8 out of 10, Exceptional, (18 reviews)
"Nice home, spacious, and conveniently located minutes from Hunter. I would stay here again. "
United States
Jim D.
The price is CA $264
CA $582 total
includes taxes & fees
Jun 15 - Jun 16
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Terrace/patio

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
8.8 out of 10, Excellent, (48 reviews)
"We were warm and cozy in the beautiful snowy woods. Thank you. "
United States
Brigit B.
The price is CA $251
CA $438 total
includes taxes & fees
Jun 14 - Jun 15
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Terrace/patio

Sauna Belleayre Cozy Cabin

Sauna Belleayre Cozy Cabin
Fleischmanns
9.6 out of 10, Exceptional, (130 reviews)
"Very cozy and comfortable, super close toBelleayre. We enjoyed the sauna after a day of skiing. Thank you for an amazing stay! "
United States
Taku T.
The price is CA $175
CA $352 total
includes taxes & fees
Jun 16 - Jun 17
Sauna Belleayre Cozy Cabin
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)
"Loved the hot tub, location being so close to the mountain, and cozy living room "
United States
Liz B.
The price is CA $409
CA $846 total
includes taxes & fees
Jun 15 - Jun 16
QUINN HOLLOW - Hunter Mountain Ski Cabin, Hot Tub
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 CA $501
CA $792 total
includes taxes & fees
Jun 14 - Jun 15
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
1 bedroom, desk, iron/ironing board, WiFi

Catskill Cabin Duplex Apartment

Catskill Cabin Duplex Apartment
Shandaken
8.4 out of 10, Very good, (26 reviews)
"This is our second time staying in this house and it was great! comfortable beds and the location was gorgeous! would absolutely stay again!"
United States
Cara K.
The price is CA $230
CA $435 total
includes taxes & fees
Jun 13 - Jun 14
Catskill Cabin Duplex Apartment
TV, fireplace, Netflix, streaming services

Catskill Cabin Cool Apartment 2nd Fl

Catskill Cabin Cool Apartment 2nd Fl
Shandaken
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time Location was good and house was well equipped"
United States
reni z.
The price is CA $245
CA $454 total
includes taxes & fees
Jun 13 - Jun 14
Catskill Cabin Cool Apartment 2nd Fl
Exterior

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Hunter
10.0 out of 10, Exceptional, (276 reviews)
"Clean and spacious lodge, with fun activities available."
United States
D L.
The price is CA $510
CA $1,301 total
includes taxes & fees
Jun 16 - Jun 17
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
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

Albergo Allegria Hotel

Albergo Allegria Hotel

10/10 Excellent
"👍"
Maria 1-night trip
Posted 2 days ago
Albergo Allegria Hotel

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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