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Most frequently booked Windham hotels

Hotel Vienna

107 State Route 296 Windham NY

2.05 km from city centre

Get rates

Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.

Eastwind Windham

5088 NY-23 Windham NY

1.79 km from city centre

CA $216

CA $271 total

Apr 1 - Apr 2

includes taxes & fees

Book a stay at this golf hotel in Windham. Enjoy free WiFi, free parking, and 2 bars/lounges. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.

Wylder Hotel Windham

19 New York 296 Windham NY

1.73 km from city centre

CA $219

CA $306 total

Mar 31 - Apr 1

includes taxes & fees

Stay at this hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.

Cave Mountain Motel

10978 STATE RTE 23 Windham NY

Free cancellation

Reserve now, pay when you stay

3.03 km from city centre

CA $193

CA $209 total

Mar 31 - Apr 1

includes taxes & fees

Stay at this motel in Windham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Windham Mountain Resort and Windham Vineyards and Winery are located nearby.

Albergo Allegria Hotel & Breakfast Restaurant

43 State Route 296 Windham NY

1.83 km from city centre

CA $217

CA $235 total

Mar 31 - Apr 1

includes taxes & fees

Book a stay at this golf B&B in Windham. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.

The Haüs Windham

218 NY-296 Windham NY

2.18 km from city centre

CA $213

CA $343 total

Apr 2 - Apr 3

includes taxes & fees

Stay at this hotel in Windham. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.

Beds on Clouds

5320 Main Street Windham NY

0.26 km from city centre

CA $262

CA $283 total

Mar 31 - Apr 1

includes taxes & fees

Stay at this guesthouse in Windham. Enjoy free WiFi, free parking, and an area shuttle (surcharge). Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Windham NY

3.2 km from city centre

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Book a stay at this family-friendly vacation home in Windham. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

Windham NY

4.28 km from city centre

Get rates

Book a stay at this family-friendly lodge in Windham. Enjoy free WiFi, a fitness center, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Windham Mountain Resort and Windham Vineyards and Winery are located nearby.

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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 family friendly Windham hotel deals

Antique Rose Inn Windham

326 State Route 296 Windham NY

CA $188

CA $203 total

Mar 31 - Apr 1

includes taxes & fees

9/10 Wonderful! (129 reviews)

Top hotels in Windham for Extended Stay

Starlite Motel

8722 Route 28 Big Indian NY

CA $174

CA $195 total

Mar 31 - Apr 1

includes taxes & fees

9.2/10 Wonderful! (299 reviews)

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.

Windham hotels essential information

Accommodation	2,143 hotels
Lowest Price	CA $195
Highest Price	CA $343
Popular hotels	Hotel Vienna, Eastwind Windham, Wylder Hotel Windham, Cave Mountain Motel, Albergo Allegria Hotel & Breakfast Restaurant, The Haüs Windham, Beds on Clouds, Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts , Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

Frequently asked questions

What are the top kid-friendly hotels in Windham?

Take some of the hassles out of traveling with youngsters by opting for a family-friendly Windham hotel. From thoughtful amenities to services that bring a smile, these properties come with perks that'll help make your getaway plain sailing: Your entourage will love staying at Restored Firehouse One Minute to Skiing on Main St. A water park and animal viewing activities are just a couple of the things that help make this property an attractive option. Alternatively, spend your Windham getaway at TOWNHOUSE-LOFT-30 ft balcony Mt View/6 BEDS/ Sleeps 6. Make the most of free WiFi, internet access and more here.

Where can I find cheap hotels in Windham?

At Travelocity you'll find really nice hotels in Windham at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Windham rather than in Windham. We may find you even better rates, too.

How do I find the best Windham hotel deals?

Simple! On Travelocity, look through the fantastic offers we've already found in Windham then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.

How much does it cost to stay in a hotel in Windham?

The cheapest hotel in Windham is CA $195 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.

How many hotels are in Windham?

There are 2,143 hotels in Windham on Travelocity.

What are the best hotels in Windham?

Windham has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Windham for you!

When is the best time to visit Windham?

If you want the joy of a fun-filled trip in peak season, visit Windham during November, December and January. If you'd prefer the peace of off-season, book a stay during quieter months, such as April, May and October.

When is the cheapest time to stay in Windham?

Based on historic data is usually the cheapest month to visit Windham. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.

Are there any great family-friendly hotels in Windham?

There are multiple hotels in Windham that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Windham. We have plenty of kid-friendly hotels in Windham to choose from on Travelocity!

Why book a hotel in Windham through Travelocity?

Because we have the top hotels in Windham! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!

How do I cancel my hotel booking in Windham on Travelocity?

Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Windham hotel reviews by fellow wanderers

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

5 out of 5

Posted 1 day ago

Travelocity Verified Review

"Just got back from a weekend at a postcard cabin in the Catskills and honestly… it was such a beautiful experience. The cabin itself was EVERYTHING I needed peaceful, cozy, and surrounded by nature. Waking up to the quiet, fresh air, and just unplugging from everything felt so refreshing. It really gave that perfect escape-from-the-city vibe. The design was super cute and minimal, and everything felt intentional and relaxing. Definitely a place to reset your mind, especially for a romantic getaway or even a solo recharge. The only small downside was that the pillow sheets didn’t seem completely clean, which threw me off a bit. It wasn’t a huge issue, but definitely something I think could be improved to make the stay feel 100% comfortable. Overall though, I would still say the experience was amazing and I’d go back again just hoping for a little more attention to detail next time. "

A verified traveller stayed at Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy