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

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Check availability on Chestertown Beach Resorts & Hotels

Tonight
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

Our top choices for Chestertown beach hotels

Beach
Reception
Beach
Property grounds

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.
฿3,530
฿4,036 total
includes taxes & fees
30 Aug - 31 Aug
The Lodge at Great Oak Landing
Terrace/patio
Suite, 1 Queen Bed | Living area
Pool
Breakfast area

2. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
฿3,190
฿3,572 total
includes taxes & fees
7 Sept - 8 Sept
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Point of interest
Room
Exterior
Exterior

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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
฿2,877
฿3,222 total
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Reception
Pool
Two queen studio suite | Bathroom
King suite whirlpool | Bathroom

4. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
฿2,743
฿3,072 total
includes taxes & fees
6 Sept - 7 Sept
Hampton Inn & Suites Edgewood/Aberdeen-South
Bathroom
Breakfast area
Lobby sitting area
Room

5. Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
Edgewood
฿2,337
฿2,617 total
includes taxes & fees
30 Aug - 31 Aug
Ramada Hotel & Conference Center by Wyndham Edgewood
Lobby
Room, 2 Queen Beds, Non Smoking
Yoga
Business centre

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
฿2,930
฿3,282 total
includes taxes & fees
7 Sept - 8 Sept
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Property amenity
Vending machine
Bathroom
Room

7. Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
Havre De Grace
฿1,827
฿2,046 total
includes taxes & fees
1 Sept - 2 Sept
Super 8 by Wyndham Havre De Grace Aberdeen Area
Exterior detail
Room, Private Bathroom (Tydings)
Dining
Exterior

8. Vandiver Inn

Vandiver Inn
Havre De Grace
฿5,248
฿5,878 total
includes taxes & fees
9 Sept - 10 Sept
Vandiver Inn
Fitness facility
Suite, 1 King Bed, Accessible (Additional Living Area)
Exterior
Pool

9. Holiday Inn Belcamp - Aberdeen Area by IHG

Holiday Inn Belcamp - Aberdeen Area by IHG
Belcamp
฿2,886
฿3,233 total
includes taxes & fees
30 Aug - 31 Aug
Holiday Inn Belcamp - Aberdeen Area by IHG
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
"Very nice hotel in an area of mixed use properties. Convenient to shopping, dining and entertainment"
Betty 1-night trip
Posted 1 day ago
Holiday Inn Express Annapolis East-Kent Island by IHG
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Our receptionist was very friendly and helpful. The room was clean and modern. Cooling system was good. Nice bathroom. The outdoor pool was clean and quiet and well maintained. Breakfast was standard travel fare but it was very fresh."
E Gaill 1-night trip
Posted 1 day 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 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.

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