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

Beach Hotels in Chestertown, Maryland

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Check availability on Chestertown Beach Hotels

Tonight
Aug 15 - Aug 16
Tomorrow
Aug 16 - Aug 17
Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30

Our top choices for Chestertown beach hotels

Private beach nearby, sun loungers, beach volleyball
Reception
Point of interest
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.
P6,636
P7,588 total
includes taxes & fees
Aug 16 - Aug 17
The Lodge at Great Oak Landing
Terrace/patio
Indoor pool
Living area
Exterior

2. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
P5,996
P6,716 total
includes taxes & fees
Aug 30 - Aug 31
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Free daily continental breakfast
Exterior
Point of interest
Exterior

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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
P5,223
P5,850 total
includes taxes & fees
Sep 14 - Sep 15
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Reception
Bathroom
Reception
Bathroom

4. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
P5,190
P5,813 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn & Suites Edgewood/Aberdeen-South
Lobby
Business center
Premium bedding, down comforters, pillowtop beds, desk
Yoga

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
P5,478
P6,136 total
includes taxes & fees
Sep 7 - Sep 8
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Exterior
WiFi (free), bed sheets
Lobby
Lobby

6. La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Edgewood
P4,609
P5,162 total
includes taxes & fees
Aug 25 - Aug 26
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Property amenity
In-room safe, desk, soundproofing, rollaway beds (surcharge)
Combined shower/tub, free toiletries, hair dryer, towels
Vending machine

7. Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
Havre De Grace
P3,519
P3,941 total
includes taxes & fees
Aug 20 - Aug 21
Super 8 by Wyndham Havre De Grace Aberdeen Area
Lobby
Terrace/patio
Restaurant
Hypo-allergenic bedding available, laptop workspace, blackout drapes

8. Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
Bel Air
P5,996
P6,716 total
includes taxes & fees
Sep 6 - Sep 7
Homewood Suites by Hilton Bel Air
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
"The room was clean, comfortable and staff were courteous , knowledgeable and professional. I would recommend this Holiday Inn and will definitely return."
Raymond 1-night trip
Posted 8 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

8/10 Good
"The door into the building from the parking lot is always locked, which is great, because it cannot be seen from the front desk, but it is difficult to enter with the room key. The key is a typical credit card-like key, but the electronic reader was wonky. Sometimes it worked and sometimes it didn’t. The cards worked well on the room doors but not on the entrance door. It was an inconvenience to walk around the building to get it the main entrance if the card did not work."
Mary Ellen 2-night trip
Posted 1 day ago
Comfort Inn & Suites Chestertown
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"Our room was clean and very quiet!"
Darlene 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 free WiFi, and it's located near a private beach. Great Oak Manor is another good option to stay near the 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 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 center. If you'd like to venture out around the area, you may want a rental car for your journey.

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