Chestertown Vacation Rentals
Check prices for these dates
Vacation Rentals in Chestertown

Amazing Modern house with a full kitchen and parking
Amazing Modern house with a full kitchen and parking

HGTV quality, private guest suite, country getaway with hot tub & fire pit
HGTV quality, private guest suite, country getaway with hot tub & fire pit

5-bedroom vacation home 5 minutes from historic Charlestown
5-bedroom vacation home 5 minutes from historic Charlestown

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Waterfront Sunset Bayview: sleeps 6
Waterfront Sunset Bayview: sleeps 6

Bayside Cottage steps from Rock Hall Harbor
Bayside Cottage steps from Rock Hall Harbor

BAYSIDE BUNGALOW
BAYSIDE BUNGALOW

Room for an Island getaway
Room for an Island getaway
Find out more about Chestertown
Find out more about Chestertown
Everything you need to know about Chestertown vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Chestertown vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chestertown in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Chestertown rentals
At Expedia, we put the best Chestertown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
Recent reviews of Chestertown properties
Recent reviews of Chestertown properties

Historic Inns of Annapolis
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Trending destinations on Expedia.com
- Destin Vacation Rentals
- Panama City Vacation Rentals
- Hilton Head Vacation Rentals
- Gulf Shores Vacation Rentals
- Key West Vacation Rentals
- Gatlinburg Vacation Rentals
- Maui Vacation Rentals
- Orlando Vacation Rentals
- Myrtle Beach Vacation Rentals
- Orange Beach Vacation Rentals
- Pigeon Forge Vacation Rentals
- Ocean City Vacation Rentals
- Outer Banks Vacation Rentals
- San Diego Vacation Rentals
- Siesta Key Vacation Rentals
- Galveston Vacation Rentals
- Clearwater Beach Vacation Rentals
- Palm Springs Vacation Rentals
- Florida Keys Vacation Rentals
- Lake Tahoe Vacation Rentals
- Lake of the Ozarks Vacation Rentals
- Florida Vacation Rentals
- Hawaii Vacation Rentals
- Michigan Vacation Rentals
- Vacation Homes in Chestertown
- Apartments in Chestertown
- Cottages in Chestertown
- Guest Houses in Chestertown
- Motels in Chestertown
- Houseboats in Chestertown
- RV Parks in Chestertown
- B&B in Chestertown
- Farmstay in Chestertown
- Condo Rentals in Chestertown
- Villas in Chestertown
- Cabin Rentals in Chestertown
- Lodges in Chestertown