Search for Cheap Deals on
Romantic Hotels in Windham

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking, and you save up to 60%!


Featured Windham Romantic Hotels

Albergo Allegria Hotel & Breakfast Restaurant
Albergo Allegria Hotel & Breakfast Restaurant
3.5 out of 5
43 State Route 296, Windham, NY
Book a stay at this golf B&B in Windham. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Windham Mountain Resort and Windham Country ...
Albergo Allegria Hotel & Breakfast Restaurant
Winwood Inn & Condominiums
Winwood Inn & Condominiums
3 out of 5
5220 NY-23, Windham, NY
Stay at this 3-star spa hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country ...
Winwood Inn & Condominiums
Hotel Vienna
Hotel Vienna
2.5 out of 5
107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Hotel Vienna
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.

Hotels with Hot Tubs in Windham

Hotel Vienna
Hotel Vienna
2.5 out of 5
107 State Route 296, Windham, NY
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Hotel Vienna
Beds on Clouds
Beds on Clouds
3 out of 5
5320 Main Street, Windham, NY
Stay at this guesthouse in Windham. Enjoy free WiFi, free parking, and an area shuttle (surcharge). Popular attractions Windham Mountain Resort and Windham Country ...
Beds on Clouds
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.

Luxury Hotels in Windham

Antique Rose Inn Windham
Antique Rose Inn Windham
3 out of 5
326 State Route 296, Windham, NY
Stay at this 3-star ski B&B in Windham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Windham Mountain Resort and Windham Country Club ...
Antique Rose Inn Windham
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.

Romantic Hotels in Windham

Looking to pop the big question? Book a romantic hotel. Digging yourself out of the doghouse? Book a romantic hotel. Regardless of the reason for spoiling your partner, a romantic hotel in Windham will do the trick.

What’s love got to do with it?

Pick a flirty place with a secluded pool and private cabanas or go for one with an in-room hot tub and a swanky restaurant on-site. Some hotels in Windham even offer romantic packages, so you can really crank up the heat. Did someone say couple’s massages? Yes, please!

Maybe it’s the little things like a ridiculously good view from your balcony or the bottle of bubbly waiting for you when you arrive, but whatever it is, your sweetie is going to flip when they see the romantic resort you booked in Windham. Just imagine the fun you’ll have with a place all to yourselves.

Love your hotel; love your savings

You’ll find yourself falling for a lot more than your honey when you book a romantic hotel in Windham. You and your partner will have hearts in your eyes when you set your sights on our swoon-worthy hotel rates. Filter hotels by:

  • Hotwire Hot Rates: Snag a Hotwire Hot Rate and you’ll find out the name of your hotel after you book. It’s like the best blind date ever.

  • Price: With rooms starting at $125, your heart may skip a beat when you see how low our prices go on Romantic hotels.

  • Amenities: Room with a view? Fancy restaurant? Room service? Sort through our amenities to find whatever puts you two in the mood.

We’re no doctor of love, but we’ve got some advice for you, don’t wait for a reason to book a romantic hotel. Surprise your honey with a getaway to Windham for no reason at all. Spice it with up a Hotwire Hot Rate—after all, every good relationship loves a little mystery.