Find beach hotels in Chestertown, MD from CA $88

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Check prices for these dates

Tonight
Nov 10 - Nov 11
Tomorrow
Nov 11 - Nov 12
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Chestertown beach hotels

A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

1. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (129 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 CA $152
CA $174 total
includes taxes & fees
Nov 12 - Nov 13
The Lodge at Great Oak Landing
A modern hotel lobby with a long dining table, several chairs, and a bar area.

2. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,004 reviews)
The price is CA $120
CA $135 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn & Suites Edgewood/Aberdeen-South
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.

3. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
2.5 star property
Middle River
9.0 out of 10, Wonderful, (980 reviews)
The price is CA $151
CA $175 total
includes taxes & fees
Nov 19 - Nov 20
SpringHill Suites Baltimore White Marsh/Middle River
A hotel with a prominent sign, multiple parking spaces, and a covered entrance.

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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
3.0 star property
Edgewood
8.2 out of 10, Very good, (1,143 reviews)
The price is CA $99
CA $111 total
includes taxes & fees
Nov 15 - Nov 16
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

5. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (315 reviews)
The price is CA $143
CA $160 total
includes taxes & fees
Dec 10 - Dec 11
Hilton Garden Inn Bel Air
A buffet area with multiple self-service stations, including trays of omelets and other prepared foods.

6. 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, (666 reviews)
The price is CA $114
CA $128 total
includes taxes & fees
Dec 11 - Dec 12
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
A hotel lobby with multiple seating areas, a coffee station, and a kitchen in the background.

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

Quality Inn & Suites Bel Air I-95 Exit 77A
2.5 star property
Edgewood
7.4 out of 10, Good, (1,224 reviews)
The price is CA $88
CA $99 total
includes taxes & fees
Nov 11 - Nov 12
Quality Inn & Suites Bel Air I-95 Exit 77A
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.

8. 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, (1,007 reviews)
The price is CA $123
CA $138 total
includes taxes & fees
Nov 29 - Nov 30
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.

9. 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, (431 reviews)
The price is CA $138
CA $154 total
includes taxes & fees
Nov 22 - Nov 23
Home2 Suites by Hilton Baltimore / Aberdeen, MD
An outdoor patio with seating, a fire pit, and a barbecue area.

10. TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (121 reviews)
The price is CA $158
CA $177 total
includes taxes & fees
Nov 25 - Nov 26
TownePlace 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.
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Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included

Top Chestertown Hotel Reviews

A modern hotel lobby with a long dining table, several chairs, and a bar area.
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood

10/10 Excellent

It is always a pleasure to stay at this location
Canada
Muhammad Imran
Reviewed October 28, 2026
Hampton Inn & Suites Edgewood/Aberdeen-South

Find out more about Chestertown

Chestertown and its attractions for beach lovers

Located just a short drive from the serene beaches of the Chesapeake Bay, Chestertown, Maryland, offers a delightful blend of charm and coastal adventure for families seeking quality experiences. Start your exploration at Wilmer Park, where the scenic waterfront beckons with picnic spots and walking trails, perfect for a leisurely afternoon with the family. Just a stone’s throw away, the Chestertown Marina invites visitors to enjoy kayaking or paddleboarding, providing a unique perspective of the town from the water. Art enthusiasts can visit the nearby Kent County Arts Council, which showcases local talents and often hosts family-friendly workshops. For a taste of local history, the Custom House Museum offers engaging exhibits that delve into the town's rich maritime heritage. After a day of exploration, families can unwind at hotels along the waterfront, where attentive service and comfortable accommodations ensure a relaxing stay. Opt for a hotel with easy access to the beach, allowing for spontaneous beach outings, while also enjoying the quaint atmosphere of Chestertown’s historic streets, lined with boutique shops and delightful eateries.

Find the best beach hotels and resorts in Chestertown

For those seeking a beach getaway in Chestertown, Maryland, these hotels offer the perfect blend of comfort and coastal charm. Enjoy sun-soaked days and stunning views at these delightful properties.

The Lodge at Great Oak Landing

  • Why it's great for the ultimate beach vacation spot: The Lodge at Great Oak Landing is an ideal retreat for beach lovers, a solid guest review rating of 8.2. Guests can enjoy direct access to a private sand beach, perfect for sunbathing and relaxation. With a variety of beach amenities including sun loungers, a waterfront location, and volleyball courts, it promises a fun-filled coastal experience.
  • Other amenities: This hotel features a shared pool with sun loungers and umbrellas, ensuring ample relaxation options. Active guests can take advantage of the 24-hour fitness facilities, while families will appreciate the playground. Additional conveniences include self-parking options, a mini-refrigerator in rooms, and stunning marina views to enjoy during your stay.
  • Nearby attractions: Kinnairds Point Drive - 19.6 km, Still Pond Station Park - 24.5 km

Frequently Asked Questions

What is Chestertown like for travelers who love the beach?

Known for its university life, Chestertown offers a lot for the traveler planning a getaway.

What's the best hotel for a beach vacation 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 to stay near the beach.

When's the best time for a beach vacation in Chestertown?

You can plan your beach trip with this snapshot of the seasons in Chestertown: The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.

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 like 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 center. If you'd like to venture out around the area, you may want a rental car for your journey.

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