Beach Hotels in Chestertown, Maryland

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Check availability on Chestertown Beach Hotels

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

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 P6,559
P7,499 total
includes taxes & fees
Apr 5 - Apr 6
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 P9,413
P10,449 total
includes taxes & fees
Apr 21 - Apr 22
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 P7,229
P9,846 total
includes taxes & fees
Apr 2 - Apr 3
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 P11,031
P12,575 total
includes taxes & fees
Apr 5 - Apr 6
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 P8,146
P9,123 total
includes taxes & fees
Apr 5 - Apr 6
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, (1,001 reviews)
"Near $95 and good place to stay"
United States
Thandavarayan
The price is P5,370
P6,014 total
includes taxes & fees
Apr 9 - Apr 10
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 P5,926
P6,637 total
includes taxes & fees
Apr 7 - Apr 8
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.
View all properties

Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included

Top Chestertown Hotel Reviews

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
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

6/10 Okay
"Breakfast was terrible and made my son and i very sick. Water pressure and temp were nonexistent and the tub clogged when showering. The tv was not working and was unplugged, which i fixed myself. When we turned on the heat the smoke detector just kept going off. Then i was told some foreign website tried to purchase extra rooms there and they wouldn't and couldnt do anything to rectify the problem."
Kristen 1-night trip
Posted 3 days ago
Best Western Kent Narrows Inn

Frequently asked questions

What is Chestertown like for travelers who love the beach?
Known for its university life, Chestertown offers a lot for the traveler planning a getaway.
What's the best hotel for a beach vacation 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 vacation in Chestertown?
You can plan your beach trip with this snapshot of the seasons in Chestertown: The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
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 like 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 center. If you'd like to venture out around the area, you may want a rental car for your journey.

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