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

Find Beach Resorts in Chestertown, MD

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Check availability on Chestertown Beach Resorts & Hotels

Tonight
1 Sept - 2 Sept
Tomorrow
2 Sept - 3 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

Our top choices for Chestertown beach hotels

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.
£91
includes taxes & fees
9 Sept - 10 Sept
The Lodge at Great Oak Landing

2. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
£285
includes taxes & fees
3 Sept - 4 Sept
Waterfront Retreat with Private Dock and Beach

3. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
£84
includes taxes & fees
10 Sept - 11 Sept
Home2 Suites by Hilton Baltimore / Aberdeen, MD

4. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
£70
includes taxes & fees
8 Sept - 9 Sept
Hampton Inn & Suites Edgewood/Aberdeen-South

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
£74
includes taxes & fees
9 Sept - 10 Sept
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

6. Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
Havre De Grace
£46
includes taxes & fees
6 Sept - 7 Sept
Super 8 by Wyndham Havre De Grace Aberdeen Area

7. Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
Bel Air
£87
includes taxes & fees
8 Sept - 9 Sept
Homewood Suites by Hilton Bel Air

8. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
£91
includes taxes & fees
6 Sept - 7 Sept
SpringHill Suites Baltimore White Marsh/Middle River

9. La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
£78
includes taxes & fees
14 Sept - 15 Sept
La Quinta Inn & Suites by Wyndham Aberdeen-APG

10. Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
Bel Air
£67
includes taxes & fees
6 Sept - 7 Sept
Candlewood Suites Aberdeen-Bel Air by IHG
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Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included
4 stars
5 stars
All-inclusive

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

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"Close to the bay"
Joshua 1-night trip
Posted 1 hour ago
Best Western Kent Narrows Inn
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

8/10 Good
"good stay"
Jose 1-night trip
Posted 7 hours 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 2 restaurants and a seasonal outdoor pool, and it's located near a private beach . Great Oak Manor is another good option for your stay near the 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 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 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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