Find Romantic Hotels in Windham, NY from $132

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Check availability on Windham Romantic Hotels

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Nov 29 - Nov 30
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Nov 30 - Dec 1
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Dec 5 - Dec 7
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Dec 12 - Dec 14

Top Windham Romantic Hotels

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, (40)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
$122 nightly
The price is $132
Dec 1 - Dec 2
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Seasonal outdoor pool
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

3.0 star property
Windham
8.8 out of 10, Excellent, (343)
"Wonderful property "
United States
Irina
$179 nightly
The price is $193
Dec 1 - Dec 2
Total with taxes and fees
Winwood Condominiums by Windham Mountain Club
Property grounds
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, (54)
"Check in & checkout and communication super easy. Location is excellent. A/C and hot water great. For 4 guys on a 2 day golf trip it worked fine. "
United States
david d.
$240 nightly
The price is $259
Dec 14 - Dec 15
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Lobby sitting area
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3.0 star property
Hunter
9.2 out of 10, Wonderful, (815)
"We had great time room was very clean and staff was very friendly and helpful definitely recommend "
United States
Muhammad
$140 nightly
The price is $151
Dec 10 - Dec 11
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
Restaurant
Urban Cowboy Lodge

Urban Cowboy Lodge

5.0 star property
Big Indian
9.2 out of 10, Wonderful, (186)
" Didn’t get the room shown on Expedia website so we were disappointed in that. Overall nice place and really enjoyed our stay. "
United States
Stuart
$157 nightly
The price is $176
Dec 3 - Dec 4
Total with taxes and fees
Urban Cowboy Lodge
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
Woodstock
8.4 out of 10, Very Good, (155)
"Beautiful historic home. We had a nice stay. "
United States
Anonymous traveler
$189 nightly
The price is $212
Dec 2 - Dec 3
Total with taxes and fees
Morning Glory B n B Woodstock NY
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, (261)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
$346 nightly
The price is $388
Dec 13 - Dec 14
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
Fridge, microwave, oven, stovetop
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Lanesville
9.8 out of 10, Exceptional, (15)
"Simply perfect! This house was clean, fully stocked of all necessities and optimally located for hiking, town hoping, art seeing and brewery bouncing. Would love to come back in the winter for its proximity to Hunter Mountain. Highly recommend!"
United States
Sarah P.
$487 nightly
The price is $490
Dec 1 - Dec 2
Total with taxes and fees
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Children's area
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, (45)
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. "
United States
Shannon F.
$279 nightly
The price is $312
Dec 7 - Dec 8
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
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, (12)
"⭐️⭐️⭐️⭐️⭐️ 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
$723 nightly
The price is $781
Dec 1 - Dec 2
Total with taxes and fees
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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Find out more about Windham

Windham attractions for couples

Windham, New York, offers a blend of outdoor adventure and charming small-town appeal, making it a perfect getaway for families and quality-seeking travelers. Start your exploration at Windham Mountain, where you can enjoy skiing in the winter or hiking and mountain biking in the warmer months, with breathtaking views of the Catskill Mountains. For a taste of local culture, visit the Windham Fine Arts Gallery, showcasing works from regional artists, perfect for those looking to appreciate art in a cozy setting. If you're seeking a unique experience, take a ride on the scenic Catskill Mountain Railroad, where you can enjoy the picturesque landscape from the comfort of a vintage train. For family fun, the Windham Country Club offers an 18-hole golf course that caters to all skill levels, along with a welcoming clubhouse for relaxing after a day on the greens. Families will appreciate a stay in the heart of Windham, where hotels like the Windham Manor provide luxurious accommodations with attentive service, allowing you to unwind after a day of exploration. The nearby local eateries and shops means convenience and quality are never far away, making your stay both enjoyable and stress-free.

Find the best romantic hotels in Windham

For couples seeking a romantic getaway in Windham, New York, these hotels offer charming accommodations and intimate settings perfect for creating lasting memories.

Cave Mountain Motel

  • Why it's great for a couples retreat: The Cave Mountain Motel offers a delightful and romantic escape with a stellar review rating of 9.6. This charming motel provides a cozy atmosphere, perfect for couples looking to enjoy a quiet getaway. Guests can indulge in a complimentary buffet breakfast, setting the perfect tone for a day of exploration or relaxation together.
  • Other amenities: The motel features stunning mountain views and access to nearby hiking trails, ideal for couples who enjoy outdoor activities. With air conditioning and self-parking, guests can enjoy a straightforward stay, focusing on each other and the beautiful surroundings.
  • Nearby attractions: Catskill State Park - 0.0 miles, Windham Mountain Resort - 2.03 miles, Ashland Park - 2.76 miles

Albergo Allegria Hotel & Breakfast Restaurant

  • Why it's great for a couples retreat: With an impressive review rating of 9.4, the Albergo Allegria Hotel & Breakfast Restaurant offers a romantic atmosphere complemented by its Victorian hotel design. The inviting ambiance, along with a charming fireplace in select rooms, creates a cozy environment perfect for couples looking to reconnect and enjoy each other's company. A delightful breakfast is served daily, enhancing the romantic experience.
  • Other amenities: The hotel features a lovely garden and terrace for couples to relax and take in the beautiful surroundings. With convenient amenities such as air conditioning, self-parking, and access to nearby hiking and biking trails, guests can easily explore and enjoy the natural beauty of Windham together.
  • Nearby attractions: Catskill State Park - 0.0 miles, Windham Country Club - 0.26 miles, Windham Mountain Resort - 1.75 miles

Hotel Vienna

  • Why it's great for a couples retreat: Hotel Vienna is an ideal retreat for travelers looking to unwind in a romantic atmosphere. With a fantastic guest review rating of 9.2, this cozy hotel features an indoor pool and beautiful mountain views, providing a serene backdrop for relaxation and intimate moments. Guests can enjoy the convenience of a complimentary breakfast each morning, setting the stage for a delightful day ahead.
  • Other amenities: Guests have access to a terrace for enjoying the fresh air, as well as nearby hiking and biking trails for adventurous couples. The hotel also offers convenient amenities such as free parking, air conditioning, and ski access, making it a perfect choice for both winter sports enthusiasts and those just looking to enjoy the scenic beauty of Windham.
  • Nearby attractions: Catskill State Park - 0.0 miles, Windham Country Club - 0.38 miles, Windham Mountain Resort - 1.88 miles

Winwood Inn & Condominiums

  • Why it's great for a couples retreat: Winwood Inn & Condominiums is a charming choice for couples seeking a romantic experience, featuring a guest review rating of 9.0. With cozy accommodations and a welcoming atmosphere, this hotel encourages intimacy with inviting spaces and nearby nature trails perfect for strolls together. The onsite kitchenette allows couples to prepare their own meals, adding a personal touch to their stay.
  • Other amenities: Guests can enjoy the outdoor tennis courts and billiards for some lighthearted competition. The hotel also features free parking, a ski shuttle for winter adventures, and access to nearby golf courses, ensuring a variety of activities for couples to enjoy together while exploring the picturesque surroundings.
  • Nearby attractions: Catskill State Park - 0.15 miles, Windham Country Club - 0.99 miles, Windham Mountain Resort - 1.41 miles

Eastwind Windham

  • Why it's great for a couples retreat: Eastwind Windham is a picturesque retreat with a review rating of 9.0, offering couples a unique romantic experience. The hotel features cozy accommodations complete with fireplaces, creating an intimate setting perfect for unwinding after a day of adventure. Guests will appreciate the serene mountain views that accompany their stay, enhancing the romantic atmosphere.
  • Other amenities: Additional features include self-parking and air conditioning for comfort and convenience. The hotel’s charming design invites couples to explore the beautiful Windham area while providing a peaceful haven to return to after a day filled with adventure.
  • Nearby attractions: Catskill State Park - 0.0 miles, Windham Country Club - 0.51 miles, Windham Mountain Resort - 1.98 miles

Top Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Thank younfor the great experience "
Eve 2-night trip
Posted 1 day ago
Hotel Vienna

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.
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.

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