Beach Hotels & Resorts in Chestertown from AU$81

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Beach Hotels

Tonight
3 Mar - 4 Mar
Tomorrow
4 Mar - 5 Mar
This weekend
6 Mar - 8 Mar
Next weekend
13 Mar - 15 Mar

Our top choices for Chestertown beach hotels

Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is AU$173
includes taxes & fees
18 Mar - 19 Mar
The Lodge at Great Oak Landing
Sun-loungers, beach towels

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (148 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is AU$739
includes taxes & fees
4 Mar - 5 Mar
5-bedroom vacation home 5 minutes from historic Charlestown
Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is AU$440
includes taxes & fees
5 Mar - 6 Mar
Waterfront Retreat with Private Dock and Beach
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (13 reviews)
"Great experience"
United States
David P.
The price is AU$485
includes taxes & fees
4 Mar - 5 Mar
18th Cent. Charm in Historic Downtown Annapolis
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.4 out of 10, Exceptional, (87 reviews)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
The price is AU$279
includes taxes & fees
4 Mar - 5 Mar
Flag House Inn
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is AU$524
includes taxes & fees
1 Apr - 2 Apr
Bayside Cottage steps from Rock Hall Harbor
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (536 reviews)
"a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back"
United States
Dieter
Vandiver Inn
Terrace/patio

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (350 reviews)
"Awesome staff, very clean, great pool Awesome breakfast!!! All good things"
United States
Patty
The price is AU$154
includes taxes & fees
22 Mar - 23 Mar
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is AU$451
includes taxes & fees
24 Mar - 25 Mar
Cozy 2br home w/ parking in downtown Annapolis
Fridge, microwave, oven, stovetop

Neptune by the Water - Pet Friendly Fenced Yard

Neptune by the Water - Pet Friendly Fenced Yard
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
The price is AU$788
includes taxes & fees
4 Mar - 5 Mar
Neptune by the Water - Pet Friendly Fenced Yard
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.
View all properties

Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Polite and kind hotel manager"
Richard 1-night trip
Posted 1 month ago
Comfort Inn & Suites Chestertown

Frequently asked questions

What is Chestertown like for travellers who love the beach?
Known for its university life, Chestertown offers a lot for the traveller planning a getaway.
What's the best place to stay for a beach holiday in Chestertown?
The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool and 3 bars/lounges, and it's located near a private beach .
When's the best time for a beach holiday in Chestertown?
You can plan your beach trip with this snapshot of year-round temperatures in Chestertown: The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What is there to see and do around Chestertown?
After arriving and checking into your hotel, you'll probably want to explore your surroundings. Beach lovers can head straight to Betterton Beach or Earle Landing for some quality time by the water. Experience the area's university life, and make time for local attractions such as Washington College and Historical Society of Kent County Maryland. For more things to see and do, consider visiting Northern Chesapeake Bay or Chesapeake Bay.
What's the best way to get to my beach hotel in Chestertown?
Here's some information to help you get to and around your beach accommodation in Chestertown more easily: To get to Chestertown, book a flight to Baltimore, MD (MTN-Martin State), the closest major airport, which is located 20.3 mi (32.7 km) from the city centre. If you'd like to venture out around the area, you may want to rent a car for your trip.