TOP Beach Resorts & Hotels in Chestertown, MD for 2026

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

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Our top choices for Chestertown beach hotels

Private beach nearby, sun-loungers, beach volleyball

1. 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.

₹10,272

₹11,744 total

includes taxes & fees

23 Sept - 24 Sept

Suite, 1 Queen Bed | Living area | 50-inch flat-screen TV with cable channels, TV

2. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

₹9,705

₹10,870 total

includes taxes & fees

28 Sept - 29 Sept

Desk, blackout curtains, iron/ironing board, cots/infant beds

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

Edgewood

₹8,399

₹9,407 total

includes taxes & fees

29 Sept - 30 Sept

Room, 2 Queen Beds, Non Smoking | Premium bedding, down duvets, pillow-top beds, desk

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

Bel Air

₹8,474

₹9,491 total

includes taxes & fees

20 Sept - 21 Sept

Two queen studio suite | Bathroom | Combined shower/bathtub, free toiletries, hair dryer, towels

King suite whirlpool | Bathroom | Combined shower/bathtub, free toiletries, hair dryer, towels

5. Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

₹8,062

₹9,029 total

includes taxes & fees

29 Sept - 30 Sept

Studio Suite, Multiple Beds, Non Smoking | Free WiFi, bed sheets

6. La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Edgewood

₹7,514

₹8,415 total

includes taxes & fees

14 Sept - 15 Sept

7. Candlewood Suites Aberdeen-Bel Air by IHG

Bel Air

₹7,731

₹8,659 total

includes taxes & fees

13 Sept - 14 Sept

Desk, laptop workspace, blackout curtains, iron/ironing board

8. SpringHill Suites Baltimore White Marsh/Middle River

Middle River

₹10,186

₹11,765 total

includes taxes & fees

20 Sept - 21 Sept

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Choose what matters most at beach hotels in Chestertown

Pool

Breakfast included

4 stars

5 stars

All-inclusive

Top Chestertown Hotel Reviews

Best Western Kent Narrows Inn

10/10 Excellent

"The staff was friendly and helpful the amenities were great and the room was clean and comfortable. It was a great value!"

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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Check availability on Chestertown Beach Resorts & Hotels

Our top choices for Chestertown beach hotels

1. The Lodge at Great Oak Landing

2. Home2 Suites by Hilton Baltimore / Aberdeen, MD

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

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

5. Hampton Inn & Suites Edgewood/Aberdeen-South

6. La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

7. Candlewood Suites Aberdeen-Bel Air by IHG

8. SpringHill Suites Baltimore White Marsh/Middle River

9. Super 8 by Wyndham Havre De Grace Aberdeen Area

Choose what matters most at beach hotels in Chestertown

Top Chestertown Hotel Reviews

Best Western Kent Narrows Inn

Frequently asked questions

Explore a world of travel with Expedia

Search Beach Resorts & Hotels in Chestertown

Change your mind

Treat yourself

Be picky

Check availability on Chestertown Beach Resorts & Hotels

Our top choices for Chestertown beach hotels

1. The Lodge at Great Oak Landing

2. Home2 Suites by Hilton Baltimore / Aberdeen, MD

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

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

5. Hampton Inn & Suites Edgewood/Aberdeen-South

6. La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

7. Candlewood Suites Aberdeen-Bel Air by IHG

8. SpringHill Suites Baltimore White Marsh/Middle River

9. Super 8 by Wyndham Havre De Grace Aberdeen Area

Choose what matters most at beach hotels in Chestertown

Top Chestertown Hotel Reviews

Best Western Kent Narrows Inn

Frequently asked questions

Explore a world of travel with Expedia