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
20 Oct - 21 Oct
Tomorrow
21 Oct - 22 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Chestertown beach hotels

A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
A campfire in a stone fire pit by a lakeside at sunset.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.

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.
£93
includes taxes & fees
21 Oct - 22 Oct
The Lodge at Great Oak Landing
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.
A hotel room with two beds, a bathroom, and a seating area.
An outdoor patio with brick walls, green chairs, and a fire pit.
A hotel with a modern facade, a covered entrance, and a red car parked outside.

2. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
£93
includes taxes & fees
29 Oct - 30 Oct
SpringHill Suites Baltimore White Marsh/Middle River
A hotel with a prominent sign, multiple parking spaces, and a covered entrance.
A hotel lobby with a reception desk, seating area, and a large screen.
A wedding ceremony in front of a large, classical building with steps leading up to the entrance.
A hotel room with a sofa, a bed with a headboard, a desk, a chair, a television, and artwork on the walls.

3. 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
£66
includes taxes & fees
22 Oct - 23 Oct
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.
A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.

4. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
£72
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.
A modern restaurant with a bar area, seating, and a counter with a menu display.
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.
A hotel room with a desk, office chair, sofa, and a dining table with chairs. There is a window with blinds, a painting on the wall, and a door leading to another room.

5. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
£82
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites by Hilton Baltimore / Aberdeen, MD
A hotel room with two beds, a nightstand with a lamp, and a wooden headboard.
A hotel reception desk with a blue wall featuring the Holiday Inn Express logo, a check-in/out sign, and a 'No Pets' sign.
A coffee station with two coffee machines, a coffee press, and various coffee accessories on a wooden counter.
An aerial view of a sports complex with multiple soccer fields, parking areas, and buildings.

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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
£70
includes taxes & fees
19 Nov - 20 Nov
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.
A dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.
A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.
A hotel room with two beds, a desk with a television, a chair, and a window with curtains.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
£75
includes taxes & fees
1 Nov - 2 Nov
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A hotel lobby with multiple seating areas, a coffee station, and a kitchen in the background.
A lobby with a beige carpet, a reception desk, and two beige armchairs.
A bathroom with a granite countertop, sink, mirror, and toilet.
A hotel room with a sofa, a bed, a desk, and a lamp.

8. Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A
Edgewood
£52
includes taxes & fees
29 Oct - 30 Oct
Quality Inn & Suites Bel Air I-95 Exit 77A
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.
A modern building with a stone facade, large windows, and outdoor seating area with chairs.
A spacious lobby with a beige sofa, blue armchairs, and a wooden coffee table. There are two floor lamps and a small round table.
A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.

9. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
£89
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Bel Air
A large, two-story barn-style building with a covered front porch and a garage.
A covered porch with white railings and a table with chairs.
A modern bathroom with a glass shower enclosure, a white toilet, and a vanity with a mirror.
A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.

10. Kent Island Resort

Kent Island Resort
Stevensville
£127
includes taxes & fees
11 Nov - 12 Nov
Kent Island Resort
View all properties

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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Property was quiet and clean and close to town."
Roberta 1-night trip
Posted 22 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 River Arts Chestertown. For more things to see and do, consider visiting Historical Society of Kent County Maryland or Chestertown Historic District.
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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