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

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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
8.0 out of 10, Very good, (91 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 £113
includes taxes & fees
19 Jul - 20 Jul
The Lodge at Great Oak Landing

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (159 reviews)
The price is £159
includes taxes & fees
3 Aug - 4 Aug
Kent Island Resort

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, (1,003 reviews)
The price is £46
includes taxes & fees
19 Jul - 20 Jul
Super 8 by Wyndham Havre De Grace Aberdeen Area

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (559 reviews)
The price is £121
includes taxes & fees
16 Jul - 17 Jul
Vandiver Inn

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, (618 reviews)
The price is £79
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

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, (388 reviews)
The price is £82
includes taxes & fees
30 Jul - 31 Jul
Home2 Suites by Hilton Baltimore / Aberdeen, MD

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,010 reviews)
The price is £80
includes taxes & fees
19 Jul - 20 Jul
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
2.0 star property
Edgewood
6.6 out of 10, (548 reviews)
The price is £75
includes taxes & fees
19 Jul - 20 Jul
Ramada Hotel & Conference Center by Wyndham Edgewood

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (886 reviews)
The price is £47
includes taxes & fees
23 Jul - 24 Jul
Super 8 by Wyndham Aberdeen MD

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (510 reviews)
The price is £71
includes taxes & fees
22 Jul - 23 Jul
Village Inn Annapolis 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.

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 Rolphs Wharf Marina.
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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