Book Kid-Friendly Hotels in Windham from $139

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Top Windham Kid Friendly Hotels

Albergo Allegria Hotel & Breakfast Restaurant

Albergo Allegria Hotel & Breakfast Restaurant

43 State Route 296, Windham, NY
$156 nightly
The price is $169 total per night from Oct 20 to Oct 21
$169 total
Oct 20 - Oct 21
Total with 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! (269 reviews)
"We loved this boutique hotel. The owners and staff were great and the breakfasts were excellent. This is a great place to stay in Windham near the Catskill Mountains."

Reviewed on Sep 6, 2025

Opens in a new windowAlbergo Allegria Hotel & Breakfast Restaurant
Hotel Vienna

Hotel Vienna

107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $139 total per night from Nov 4 to Nov 5
$139 total
Nov 4 - Nov 5
Total with 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! (662 reviews)
"Wonderful place, enjoyed out balcony. Loved being able to easily get to the windham path trail"

Reviewed on Oct 13, 2025

Opens in a new windowHotel 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 Oct 20 to Oct 21
$146 total
Oct 20 - Oct 21
Total with 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! (124 reviews)
"Very entertaining owner, comfortable bed, quiet at night, bathroom shareable with the other two rooms, all very clean and cure for details. Great breakfast, not very far from Windham."

Reviewed on Sep 23, 2025

Opens in a new windowAntique Rose Inn Windham
Winwood Condominiums by Windham Mountain Club
Great for families

Winwood Condominiums by Windham Mountain Club

5220 NY-23, Windham, NY
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! (340 reviews)

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

Travelers say...
"Clean rooms"

Reviewed on Oct 11, 2025

Opens in a new windowWinwood Condominiums by Windham Mountain Club
Beds on Clouds

Beds on Clouds

5320 Main Street, Windham, NY
$183 nightly
The price is $197 total per night from Oct 20 to Oct 21
$197 total
Oct 20 - Oct 21
Total with 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

Opens in a new windowBeds 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
$129 nightly
The price is $139 total per night from Nov 4 to Nov 5
$139 total
Nov 4 - Nov 5
Total with taxes and fees
9.2/10 Wonderful! (662 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 $139 per night. Our prices range up $197 per night if you want to enjoy the high life.


How many family-friendly hotels are there in Windham?


With over 2,077 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.


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