Find Romantic Hotels in Windham, NY from $324

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Windham Romantic Hotels

Check prices for these dates

Tonight
Aug 23 - Aug 24
Tomorrow
Aug 24 - Aug 25
Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7

Top Windham Romantic Hotels

Our top choices for Windham romantic hotels

Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (249)
"A beautiful quiet setting! "
$289 nightly
The price is $324
Sep 2 - Sep 3
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
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.

Top Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Beautiful property. Lovely room with a very comfortable bed. Extremely helpful desk staff—I would like to extend my thanks especially to her. "
Laura 1-night trip
Posted 3 days ago
Hotel Vienna

Find out more about Windham

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

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.