Book Kid-Friendly Hotels in Chestertown from $70
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 Chestertown Kid Friendly Hotels
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Families like: Kitchen, close to beach, extra beds/cribs, games and toys
Reviewed on Nov 8, 2024
Comfort Inn & Suites Chestertown
Reviewed on Mar 26, 2025
Driftwood Inn
Reviewed on Oct 16, 2024
Hotels With Pools in Chestertown
Comfort Inn & Suites Chestertown
Book a stay at the best kid-friendly hotels in Chestertown
How much does it cost to stay in a family hotel in Chestertown?
You can book a stay at a kid-friendly resort in Chestertown from just $70 per night. Our prices range up $114 per night if you want to enjoy the high life.
How many family-friendly hotels are there in Chestertown?
With over 1,055 hotels in Chestertown, 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 Chestertown?
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 Chestertown?
At Travelocity, you can book the best family-friendly Chestertown 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 Chestertown?
When you book a kid-friendly Chestertown 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 Chestertown?
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 Chestertown with Travelocity.
When is the cheapest time to go to Chestertown with your family?
The cheapest time to visit Chestertown is usually .
When is the best time to go to Chestertown with your kids?
The most popular months are and are great for booking in at a Chestertown 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 Chestertown 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.
Top landmarks in Chestertown
Washington College
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Chestertown hotels essential information
Accommodation | 1,055 hotels |
|---|---|
Lowest Price | $70 |
Highest Price | $114 |
Popular hotels | Comfort Inn & Suites Chestertown, Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town, Driftwood Inn |
Package deals, things to do & more in Chestertown
Fun things to do with kids in Chestertown
Best flights+hotels package deals to Chestertown
Our top All Inclusive family-friendly hotels in Chestertown
Villas, cabins and more rentals in Chestertown
Recent Chestertown Hotel Reviews By Fellow Wanderers
Historic Inns of Annapolis
Explore More Ways to Travel with Travelocity
- Explore More
- Other Hotel Types
- Other Accommodation Types
- Explore Neighborhoods in Chestertown
- Pet Friendly Hotels in other Cities
An attraction
- Hotels near Washington College
- Hotels near Rolphs Wharf Marina
- Hotels near River Arts Chestertown
- Hotels near Historical Society of Kent County Maryland
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Wilmer Park
- Hotels near Crumpton Auction
- Hotels near Baltimore Cruise Terminal
- Hotels near U.S. Naval Academy
- Hotels near Ripken Stadium
- Hotels near Chesapeake Bay Bridge
- Hotels near Annapolis City Dock
- Hotels near Sandy Point State Park
- Hotels near White Marsh Mall
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Susquehanna River
- Hotels near Fort McHenry
- Hotels near Harford Community College
- Hotels near Cedar Lane Regional Park
- Hotels near Rock Hall Harbor
- Hotels near Havre de Grace Promenade
- Hotels near Cal Ripken Museum
- Hotels near Maryland State House
- Hotels near Annapolis Maritime Museum
- Hotels near Bohemia Vista Marina
- Hotels near Elk Neck State Park
- Hotels near Queenstown Premium Outlets
- Hotels near Bulle Rock Golf Course
- Hotels near Queenstown Harbor Golf Club
- Hotels near William Paca House
- Hotels near Patterson Park
- Hotels near Chesapeake Bay Environmental Center
- Hotels near Concord Point Lighthouse
- Hotels near Gunpowder Falls State Park
Hotels by star rating
- Hotels with Air Conditioning in Chestertown
- Hotels with Free Parking in Chestertown
- Hotels with Restaurants in Chestertown
- Adventure Hotels in Chestertown
- Hotels with Free Breakfast in Chestertown
- Romantic Getaways & Hotels in Chestertown
- Pet Friendly Hotels in Chestertown
- Beach Resorts & Hotels in Chestertown
- Hotels with Pools in Chestertown
- Historic Hotels in Chestertown
- Hotels with a Gym in Chestertown
- Hotel Wedding Venues in Chestertown
- Cheap Hotels in Chestertown
- Hotels with an Indoor Pool in Chestertown
- Hotels with Bar in Chestertown
- Hotels with Shopping in Chestertown
- Golf Resorts & Hotels in Chestertown
- Convention Center Hotels in Chestertown
- Hotels with Suites in Chestertown
- Spa Resorts & Hotels in Chestertown
- Oceanfront Hotels in Chestertown
- Hotels with smoking rooms in Chestertown
- Hotels with Kitchenettes in Chestertown
- Arcade Hotels in Chestertown
- Luxury Hotels in Chestertown
Areas of Chestertown
- Annapolis Hotels
- Dover Hotels
- St. Michaels Hotels
- Delaware Beaches Hotels
- Perryville Hotels
- Edgewood Hotels
- Grasonville Hotels
- Havre De Grace Hotels
- Aberdeen Hotels
- Easton Hotels
- Bel Air Hotels
- Glen Burnie Hotels
- Chesapeake Bay Hotels
- Elkton Hotels
- Stevensville Hotels
- Rosedale Hotels
- Eastern Shore Hotels
- White Marsh Hotels
- Middletown Hotels
- Kent Island Hotels
- North East Hotels
- Appalachian Mountains Hotels
- Pasadena Hotels
- Rock Hall Hotels
- Parkville Hotels
- Chesapeake City Hotels
- Galena Hotels
- Parole Hotels
- Harrington Hotels
- Smyrna Hotels
- Severna Park Hotels
- Essex Hotels
- Middle River Hotels
- Dundalk Hotels
- Arnold Hotels
- Kent Narrows Hotels
- Queenstown Hotels
- Chester Hotels
- Centreville Hotels
- Crownsville Hotels
- Kid Friendly Hotels in Las Vegas
- Kid Friendly Hotels in Washington
- Kid Friendly Hotels in New York City
- Kid Friendly Hotels in Myrtle Beach
- Kid Friendly Hotels in Orlando
- Kid Friendly Hotels in Chicago
- Kid Friendly Hotels in San Diego
- Kid Friendly Hotels in Miami
- Kid Friendly Hotels in San Francisco
- Kid Friendly Hotels in London
- Kid Friendly Hotels in Palm Springs
- Kid Friendly Hotels in Cancun
- Kid Friendly Hotels in Miami Beach
- Kid Friendly Hotels in Florida
- Kid Friendly Hotels in Boston
- Kid Friendly Hotels in New Orleans
- Kid Friendly Hotels in Los Angeles
- Kid Friendly Hotels in Fort Lauderdale
- Kid Friendly Hotels in Ocean City
- Kid Friendly Hotels in Rome