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Our top choices for Chestertown beach hotels

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (83 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 £112
includes taxes & fees
4 Jun - 5 Jun
The Lodge at Great Oak Landing

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (991 reviews)
The price is £46
includes taxes & fees
2 Jun - 3 Jun
Super 8 by Wyndham Havre De Grace Aberdeen Area

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (141 reviews)
The price is £152
includes taxes & fees
1 Jun - 2 Jun
Kent Island Resort

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is £319
includes taxes & fees
2 Jun - 3 Jun
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (547 reviews)
The price is £120
includes taxes & fees
31 May - 1 Jun
Vandiver Inn

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (340 reviews)
The price is £91
includes taxes & fees
31 May - 1 Jun
Fairfield Inn & Suites by Marriott Aberdeen

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)
The price is £74
includes taxes & fees
7 Jun - 8 Jun
La Quinta Inn & Suites by Wyndham Aberdeen-APG

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, (378 reviews)
The price is £81
includes taxes & fees
7 Jun - 8 Jun
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,003 reviews)
The price is £77
includes taxes & fees
14 Jun - 15 Jun
Hampton Inn & Suites Edgewood/Aberdeen-South

SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
3.0 star property
Bel Air
8.8 out of 10, Excellent, (384 reviews)
The price is £97
includes taxes & fees
7 Jun - 8 Jun
SpringHill 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.

Choose what matters most at beach hotels in Chestertown

Find out more about Chestertown

Chestertown and its attractions for beach lovers

Chestertown, Maryland, beautifully located along the Chester River, offers a delightful blend of historical charm and natural beauty, perfect for beach-loving travellers. Begin your adventure at Wilmer Park, where sandy shores meet lush green spaces; it's an excellent spot for a family picnic or a leisurely walk along the waterfront, with beautiful views of the river. Just a short drive away, you can explore the serene, sandy stretches of Sandy Point State Park, where swimming, sunbathing, and beachcombing await. For a unique experience, head to the nearby Eastern Neck National Wildlife Refuge, where you can enjoy quiet walks alongside tidal marshes while spotting diverse bird species. If you're keen on sailing or kayaking, Chestertown’s local marinas provide rentals and guided tours, giving you an adventurous way to explore the waterways. When it comes to accommodation, consider staying at one of the charming inns or boutique hotels in the heart of Chestertown, where attentive service and comfortable amenities ensure a relaxing retreat after a day of exploration. The historic district's cobblestone streets are perfect for evening strolls, with local eateries offering fresh seafood and regional delicacies, making your stay not just memorable but a true taste of Maryland's coastal culture.

Top Chestertown Hotel Reviews

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 free WiFi, 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 River Arts Chestertown. For more things to see and do, consider visiting Chestertown Historic District 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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