Book Kid-Friendly Hotels in Windham from $146

Find & compare hotels, resorts and vacation rentals for the whole family

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top Windham Kid Friendly Hotels

Albergo Allegria Hotel & Breakfast Restaurant

Albergo Allegria Hotel & Breakfast Restaurant

43 State Route 296, Windham, NY
$145 nightly
The price is $157 total per night from Jul 13 to Jul 14
$157 total
Jul 13 - Jul 14
Total includes taxes and fees
A restaurant, free self parking, and a terrace are among this bed & breakfast's amenities. WiFi in public areas is free. A business center, a garden, and a lobby ...
9.6/10 Exceptional! (265 reviews)
Wonderful stay!
"We enjoyed our stay, the room was very comfortable, the bathroom very clean and convenient to town."

Reviewed on Jul 7, 2025

Albergo Allegria Hotel & Breakfast Restaurant
Hotel Vienna

Hotel Vienna

107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $146 total per night from Jul 21 to Jul 22
$146 total
Jul 21 - Jul 22
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of ...
9.2/10 Wonderful! (584 reviews)
"People were great. It was modern and extremely clean. The bed was very comfortable. Great shower."

Reviewed on Jul 6, 2025

Hotel Vienna
Antique Rose Inn Windham

Antique Rose Inn Windham

326 State Route 296, Windham, NY
$135 nightly
The price is $146 total per night from Jul 16 to Jul 17
$146 total
Jul 16 - Jul 17
Total includes taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Enjoy the ski shuttle and onsite ski passes. ...
9/10 Wonderful! (121 reviews)
"We did not expect to share a bathroom. We should of done our homework on the place. Its a lovely place to stay. Owner is very friendly, breakfast was accommodating to our wishes."

Reviewed on Jun 29, 2025

Antique Rose Inn Windham
Winwood Condominiums by Windham Mountain Club
Great for families

Winwood Condominiums by Windham Mountain Club

5220 NY-23, Windham, NY
$178 nightly
The price is $192 total per night from Jul 13 to Jul 14
$192 total
Jul 13 - Jul 14
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi, free self parking, and a free ski shuttle. Take advantage of ski passes on site, and enjoy sledding. ...
8.6/10 Excellent! (324 reviews)

Families like: Outdoor pool, game room, skiing nearby, laundry

Go for the views and town, stay for the pool
"Interesting place. Obviously a ski condo, so not too busy in the summer. Top-notch pool in a gorgeous setting. Rest of the complex was surprisingly ramshackle and of motel-like construction, unusual for a condo."

Reviewed on Jul 7, 2025

Winwood Condominiums by Windham Mountain Club
Beds on Clouds

Beds on Clouds

5320 Main Street, Windham, NY
$206 nightly
The price is $222 total per night from Jul 11 to Jul 12
$222 total
Jul 11 - Jul 12
Total includes taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. You'll appreciate the area shuttle, terrace, and garden.
7.4/10 Good! (67 reviews)
"Old, outdated everything inside, musty, no WiFi, no heat in the bathroom."

Reviewed on Jan 19, 2025

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.

Hotels With Pools in Windham

Hotel Vienna

Hotel Vienna

107 State Route 296, Windham, NY
$135 nightly
The price is $146 total per night from Jul 21 to Jul 22
$146 total
Jul 21 - Jul 22
Total includes taxes and fees
9.2/10 Wonderful! (584 reviews)

Book a stay at the best kid-friendly hotels in Windham

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


You can book a stay at a kid-friendly resort in Windham from just $146 per night. Our prices range up $222 per night if you want to enjoy the high life.


How many family-friendly hotels are there in Windham?


With over 2,052 hotels in Windham, you have a great selection of kid-friendly places to stay. Whether you’re looking for a cheap-and-cheerful property with plenty of space or an activity-filled kid-friendly resort, there’s a getaway to suit your style and your budget at Travelocity.


What is Travelocity’s cancellation policy for family hotels in Windham?


We offer free cancellation on select hotels. Policies can vary per property so it's best to check before you book. If you need to amend or cancel your vacation, just visit our Customer Service Portal. 


What are the best kid-friendly hotels in Windham?


At Travelocity, you can book the best family-friendly Windham hotel for you and your family by filtering your search by price, property type, and a range of amenities such as breakfast included or free airport shuttle. Use the map to see where the hotels are and the attractions they’re near.


What should I expect in the family-friendly hotels in Windham?


When you book a kid-friendly Windham resort, you can expect fun for all the family. Think pools, waterparks, and hot tubs. Think babysitting, kids’ menus, games rooms, and sport facilities—discover your ideal family vacation. Many resorts keep the kids happy, so you can indulge in bars, restaurants, and spas. Check details for each property as offers may vary.


How can I find family hotel deals in Windham?


Just enter your travel dates and sort your results by price. You can even filter your results by budget, so you’ll only see the deals that are right for your pocket. It’s easy to find great deals on family-friendly hotels in Windham with Travelocity. 


When is the cheapest time to go to Windham with your family?


The cheapest time to visit Windham is usually .


When is the best time to go to Windham with your kids?


The most popular months are and are great for booking in at a Windham kid-friendly resort. If you want a quieter vacation—or the kids aren’t in school yet— are usually less busy, but you can find incredible deals all year round with Travelocity. 


Why book a Windham child-friendly hotel with Travelocity?


Because we search the entire market, so you don’t have to. You’ll find great deals on everything from weekend trips to two-week family vacations. Whatever your budget or your wish list, we’ve got what you’re looking for.


Package deals, things to do & more in Windham


Recent Windham Hotel Reviews By Fellow Wanderers

Explore More Ways to Travel with Travelocity

Explore More Ways to Travel with Travelocity