Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Check availability on Chestertown Beach Resorts & Hotels

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
3.0 star property
Chestertown
7.8 out of 10, Good, (87 reviews)
  • cleanliness
    Escape to waterfront tranquility with a private beach just 0.25 miles away, where sandy shores, volleyball courts, and loungers await.
The price is Rp2.342.901
Rp2.678.840 total
includes taxes & fees
22 Jun - 23 Jun
The Lodge at Great Oak Landing
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (144 reviews)
The price is Rp2.625.359
Rp3.511.163 total
includes taxes & fees
5 Jul - 6 Jul
Kent Island Resort
Property amenity

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (1,002 reviews)
The price is Rp940.702
Rp1.053.586 total
includes taxes & fees
22 Jun - 23 Jun
Super 8 by Wyndham Havre De Grace Aberdeen Area
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (553 reviews)
The price is Rp2.580.681
Rp2.890.361 total
includes taxes & fees
28 Jun - 29 Jun
Vandiver Inn
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,888 reviews)
The price is Rp1.596.704
Rp2.425.890 total
includes taxes & fees
12 Jul - 13 Jul
Historic Inns of Annapolis
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, (380 reviews)
The price is Rp1.728.044
Rp1.935.408 total
includes taxes & fees
28 Jun - 29 Jun
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Exterior

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,010 reviews)
The price is Rp1.657.562
Rp1.856.470 total
includes taxes & fees
17 Jun - 18 Jun
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Combined shower/bathtub, free toiletries, hair dryer, towels

Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
2.0 star property
Edgewood
6.6 out of 10, (533 reviews)
The price is Rp1.580.528
Rp1.770.192 total
includes taxes & fees
17 Jun - 18 Jun
Ramada Hotel & Conference Center by Wyndham Edgewood
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
The price is Rp4.023.662
Rp4.586.985 total
includes taxes & fees
21 Jun - 22 Jun
Flag House Inn
Terrace/patio

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (344 reviews)
The price is Rp1.938.781
Rp2.171.435 total
includes taxes & fees
21 Jun - 22 Jun
Fairfield Inn & Suites by Marriott Aberdeen
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.
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Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included

Top Chestertown Hotel Reviews

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"Staff is always incredibly helpful and pleasant."
Brittney 1-night trip
Posted 17 hours ago
Best Western Kent Narrows Inn
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

8/10 Good
"Comfortable beds. Breakfast was decent, with hot and cold options. Shower did not have pressure. Pool was small but nice. Unfortunately we were there Wednesday -Sunday and never were given new towels or a room cleaning. And the last morning we found ants in the room."
Caroline 1-night trip
Posted 2 days 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 free WiFi, 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 River Arts Chestertown. For more things to see and do, consider visiting Chestertown Historic District or Rolphs Wharf Marina.
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.