Chestertown Beach Resorts from RM399

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Check availability on Chestertown Beach Resorts

Tonight
1 Apr - 2 Apr
Tomorrow
2 Apr - 3 Apr
This weekend
3 Apr - 5 Apr
Next weekend
10 Apr - 12 Apr

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 RM435
RM497 total
includes taxes & fees
9 Apr - 10 Apr
The Lodge at Great Oak Landing
Exterior

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is RM628
RM697 total
includes taxes & fees
21 Apr - 22 Apr
Haven Point Inn and Gallery
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (134 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is RM522
RM701 total
includes taxes & fees
8 Apr - 9 Apr
Kent Island Resort
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (91 reviews)
"The room was over the garage. You couldn’t stand up in half the room as the ceiling was too low. Multiple tripping areas walking into and out of the space. No heat in bathroom. You have to walk to the front of house to enter for coffee in the morning. They have the nerve to charge you to park at the house. "
United States
Richard
The price is RM735
RM838 total
includes taxes & fees
5 Apr - 6 Apr
Flag House Inn
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (538 reviews)
"As always we loved our stay! Definitely will be coming back "
United States
John
The price is RM540
RM605 total
includes taxes & fees
6 Apr - 7 Apr
Vandiver Inn
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, (1,002 reviews)
"Near $95 and good place to stay"
United States
Thandavarayan
The price is RM356
RM399 total
includes taxes & fees
15 Apr - 16 Apr
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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, (358 reviews)
"Staff was very friendly and it was a perfect location for us"
United States
Ryan
The price is RM409
RM459 total
includes taxes & fees
3 May - 4 May
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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

8/10 Good
"Good to have a hot breakfast. Potatoes were slightly undercooked and we were there for 4 nights and very little variations in the menu. Would have been nice if there was a change in protein during our stay. The winner is the pool and hot tub. The first night we were there, we were able to get the steam room going, but after that, we couldn't get it to wok. Nevertheless, love that these were available especially on a cold night."
Lynn 4-night trip
Posted 6 hours ago
Best Western Kent Narrows Inn
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

8/10 Good
"Clean, quiet. "
Ann Marie 2-night trip
Posted 3 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 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 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 Historical Society of Kent County Maryland. For more things to see and do, consider visiting Rolphs Wharf Marina or Northern 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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