Beach Resorts in Chestertown

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Check availability on Chestertown Beach Resorts

Tonight
25 Feb - 26 Feb
Tomorrow
26 Feb - 27 Feb
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

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)
  • cleanliness
    Escape to waterfront tranquility with a private beach just 0.25 miles away, where sandy shores, volleyball courts, and loungers await.
The price is S$156
includes taxes & fees
26 Mar - 27 Mar
The Lodge at Great Oak Landing
Exterior

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (34 reviews)
134 Prince - Luxury Boutique Hotel
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.4 out of 10, Exceptional, (87 reviews)
The price is S$262
includes taxes & fees
1 Mar - 2 Mar
Flag House Inn
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (535 reviews)
Vandiver Inn
Free daily continental breakfast

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (574 reviews)
The price is S$122
includes taxes & fees
27 Feb - 28 Feb
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
View from property

TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.2 out of 10, Wonderful, (106 reviews)
The price is S$187
includes taxes & fees
27 Feb - 28 Feb
TownePlace Suites by Marriott Edgewood Aberdeen
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
Sea view

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Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Polite and kind hotel manager"
Richard 1-night trip
Posted 1 month 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 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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