Book Cheap Hotels in Windham

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Check hotel availability in Windham

Tonight
Check prices in Windham for tonight, Dec 13 - Dec 14
Dec 13 - Dec 14
Tomorrow night
Check prices in Windham for tomorrow night, Dec 14 - Dec 15
Dec 14 - Dec 15
Next weekend
Check prices in Windham for next weekend, Dec 19 - Dec 21
Dec 19 - Dec 21

Most frequently booked Windham hotels

Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296 Windham NY
Free cancellation
Reserve now, pay when you stay
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

Eastwind Windham

2 out of 5
5088 NY-23 Windham NY
1.79 km from city centre
The price is CA $398 per night
CA $398
CA $474 total
Dec 21 - Dec 22
includes taxes & fees
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296 Windham NY
1.73 km from city centre
The price is CA $283 per night
CA $283
CA $375 total
Dec 14 - Dec 15
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.
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

3 out of 5
5220 NY-23 Windham NY
Free cancellation
Reserve now, pay when you stay
0.94 km from city centre
The price is CA $222 per night
CA $222
CA $240 total
Dec 15 - Dec 16
includes taxes & fees
Book a stay at this ski hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
The Haüs Windham

The Haüs Windham

2 out of 5
218 NY-296 Windham NY
2.18 km from city centre
The price is CA $215 per night
CA $215
CA $344 total
Dec 15 - Dec 16
includes taxes & fees
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Cave Mountain Motel

Cave Mountain Motel

2.5 out of 5
10978 STATE RTE 23 Windham NY
3.03 km from city centre
The price is CA $191 per night
CA $191
CA $207 total
Dec 17 - Dec 18
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.
Antique Rose Inn Windham

Antique Rose Inn Windham

3 out of 5
326 State Route 296 Windham NY
3.04 km from city centre
The price is CA $186 per night
CA $186
CA $201 total
Jan 7 - Jan 8, 2026
includes taxes & fees
Book a stay at this ski B&B in Windham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Beds on Clouds

Beds on Clouds

3 out of 5
5320 Main Street Windham NY
0.26 km from city centre
The price is CA $260 per night
CA $260
CA $281 total
Dec 15 - Dec 16
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.
Parking included
Free WiFi
A'Neils Windham Ski Lodge & Family Retreat

A'Neils Windham Ski Lodge & Family Retreat

Windham NY
4.49 km from city centre
Get rates
Book a stay at this ski vacation home in Windham. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Windham Mountain Resort and Ashland Park 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

Antique Rose Inn Windham

326 State Route 296 Windham NY
The price is CA $186 per night from Jan 7 to Jan 8
CA $186
CA $201 total
Jan 7 - Jan 8, 2026
includes taxes & fees
9/10 Wonderful! (125 reviews)

Top hotels in Windham for Extended Stay

The ultimate resort experience. Pool, hot tub, sauna, steam room, exercise room.

The ultimate resort experience. Pool, hot tub, sauna, steam room, exercise room.

Hunter NY
10/10 Exceptional! (5 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
2,092 hotels
Lowest Price
CA $191
Highest Price
CA $474
Popular hotels
Hotel Vienna, Eastwind Windham, Wylder Hotel Windham, Winwood Condominiums by Windham Mountain Club , The Haüs Windham, Cave Mountain Motel, Antique Rose Inn Windham, Beds on Clouds, A'Neils Windham Ski Lodge & Family Retreat

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 $191 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 2,092 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

Eastwind Windham

Eastwind Windham

5 out of 5
Posted 5 days ago
Travelocity Verified Review
"Staff helpful and friendly."
A verified traveller stayed at Eastwind Windham
Eastwind Windham

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