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Tonight
Check prices in Windham for tonight, Sep 29 - Sep 30
Sep 29 - Sep 30
Tomorrow night
Check prices in Windham for tomorrow night, Sep 30 - Oct 1
Sep 30 - Oct 1
This weekend
Check prices in Windham for this weekend, Oct 2 - Oct 4
Oct 2 - Oct 4
Next weekend
Check prices in Windham for next weekend, Oct 9 - Oct 11
Oct 9 - Oct 11

Most frequently booked Windham hotels

Hotel Vienna

Hotel Vienna

3 out of 5
107 State Route 296 Windham NY
2.05 km from city centre
The price is CA $165 per night
CA $165
CA $202 total
Oct 1 - Oct 2
includes taxes & fees
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.
Pool
Breakfast included
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 $380 per night
CA $380
CA $481 total
Oct 29 - Oct 30
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.
Pool
Pet-friendly
Eastwind Windham

Eastwind Windham

3.5 out of 5
5088 NY-23 Windham NY
1.79 km from city centre
The price is CA $356 per night
CA $356
CA $428 total
Oct 18 - Oct 19
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.
Pet-friendly
Parking included
Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn

141 South St Windham NY
0.89 km from city centre
The price is CA $179 per night
CA $179
CA $193 total
Oct 1 - Oct 2
includes taxes & fees
Book a stay at this ski motel in Windham. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Parking included
Free WiFi
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 $175 per night
CA $175
CA $402 total
Oct 7 - Oct 8
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.
Pet-friendly
Parking included
Albergo Allegria Hotel

Albergo Allegria Hotel

3.5 out of 5
43 State Route 296 Windham NY
1.83 km from city centre
The price is CA $246 per night
CA $246
CA $266 total
Sep 30 - Oct 1
includes taxes & fees
Book a stay at this golf B&B in Windham. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Parking included
Free WiFi
The Winwood Condominiums

The Winwood Condominiums

3 out of 5
5220 NY-23 Windham NY
0.94 km from city centre
The price is CA $212 per night
CA $212
CA $229 total
Sep 30 - Oct 1
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.
Pool
Parking included
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

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.
Pet-friendly
Free WiFi
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St Hunter NY
Free cancellation
Reserve now, pay when you stay
12.54 km from city centre
The price is CA $207 per night
CA $207
CA $254 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this hotel in Hunter. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hunter Mountain and H Ski Lift are located nearby.
Breakfast included
Pet-friendly
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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 $191 per night from Sep 30 to Oct 1
CA $191
CA $207 total
Sep 30 - Oct 1
includes taxes & fees

Top hotels in Windham for Extended Stay

Starlite Motel

Starlite Motel

8722 Route 28 Big Indian NY
The price is CA $177 per night from Sep 30 to Oct 1
CA $177
CA $198 total
Sep 30 - Oct 1
includes taxes & fees
9.2/10 Wonderful! (314 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
2,176 hotels
Lowest Price
CA $193
Highest Price
CA $481
Popular hotels
Hotel Vienna, Wylder Hotel Windham, Eastwind Windham, Jimmy OConnors Windham Mountain Inn, The Haüs Windham, Albergo Allegria Hotel, The Winwood Condominiums, Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge, Hunter Lodge, a Bluebird by Lark

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 $193 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 2,176 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

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

4 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Overall, the cabin was nice. Especially if you're only planning on staying a few days. But for the price you pay for 2 nights, they could have better utensils, pan, a few more cooking utensils and a kettle for the hot water. These are just a few inexpensive amenities that these places should all have! Because most people are probably cooking there own food nowadays either by choice or the fact that there's nothing close by. But aside from the kitchen issues, this was a very nice, enjoyable getaway. I would definitely recommend it to anyone who loves the outdoors!"
A verified traveller stayed at Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy