An aerial view of a town with a river, buildings, and surrounding greenery.

Chestertown Hotel Guide - Beach Hotels in Chestertown, Maryland

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Check availability on Chestertown Beach Hotels

Tonight
29 Aug - 30 Aug
Tomorrow
30 Aug - 31 Aug
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

Our top choices for Chestertown beach hotels

Private beach nearby, sun-loungers, beach volleyball
Property grounds
Point of interest
Private beach nearby, sun-loungers, beach volleyball

1. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
  • Escape to waterfront tranquility with a private beach just 0.25 miles away, where sandy shores, volleyball courts, and loungers await.
€106
includes taxes & fees
30 Aug - 31 Aug
The Lodge at Great Oak Landing
Terrace/patio
Suite, 1 Queen Bed | Living area
Exterior
Indoor pool

2. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
€94
includes taxes & fees
7 Sept - 8 Sept
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Beach nearby
Coffee/tea maker, fridge, microwave, stovetop
Exterior
Interior

3. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
€329
includes taxes & fees
30 Aug - 31 Aug
Waterfront Retreat with Private Dock and Beach
Reception
Standard Room | Bathroom
Standard Room | Bathroom
Pool

4. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
€81
includes taxes & fees
6 Sept - 7 Sept
Hampton Inn & Suites Edgewood/Aberdeen-South
Lobby
Room, 2 Queen Beds, Non Smoking
Yoga
Exterior

5. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
€86
includes taxes & fees
8 Sept - 9 Sept
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Point of interest
Exterior
Exterior
Hair dryer, towels

6. Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
€84
includes taxes & fees
28 Sept - 29 Sept
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Property amenity
Exterior
Vending machine
In-room safe, desk, soundproofing, rollaway beds

7. Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
Havre De Grace
€54
includes taxes & fees
6 Sept - 7 Sept
Super 8 by Wyndham Havre De Grace Aberdeen Area
Exterior
Free daily buffet breakfast
Lobby
Lobby

8. La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
€92
includes taxes & fees
11 Sept - 12 Sept
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Reception
Restaurant
Standard Single Room, 1 King Bed
Superior Single Room, Balcony | Terrace/patio

9. Kent Island Resort

Kent Island Resort
Stevensville
€183
includes taxes & fees
14 Sept - 15 Sept
Kent Island Resort
Combined shower/bathtub, free toiletries, hair dryer, towels
Desk, blackout curtains, iron/ironing board, free cots/infant beds
Free daily continental breakfast
Property entrance

10. Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
Edgewood
€69
includes taxes & fees
30 Aug - 31 Aug
Ramada Hotel & Conference Center by Wyndham Edgewood
View all properties

Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included
4 stars
5 stars
All-inclusive

Top Chestertown Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Great view of the water."
LINDA 1-night trip
Posted 2 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG

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 2 restaurants and a seasonal outdoor pool, and it's located near a private beach . Great Oak Manor is another good option for your stay near the 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 Main Beach for some quality time by the water. Experience the area's university life, and make time for local attractions such as Washington College and Chestertown Historic District. 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.