Top Beach Resorts in Chestertown

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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.

S$157

includes taxes & fees

17 Sept - 18 Sept

2. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

S$139

includes taxes & fees

7 Sept - 8 Sept

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

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

Edgewood

S$125

includes taxes & fees

1 Sept - 2 Sept

Combined shower/bathtub, free toiletries, hair dryer, towels

4. Ramada Hotel & Conference Center by Wyndham Edgewood

Edgewood

S$101

includes taxes & fees

26 Aug - 27 Aug

5. Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

S$119

includes taxes & fees

6 Sept - 7 Sept

Premium bedding, down duvets, pillow-top beds, desk

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

Bel Air

S$127

includes taxes & fees

6 Sept - 7 Sept

In-room safe, desk, laptop workspace, free WiFi

7. Candlewood Suites Aberdeen-Bel Air by IHG

Bel Air

S$115

includes taxes & fees

30 Aug - 31 Aug

Iron/ironing board (on request), free WiFi, individually decorated

8. Kent Island Resort

Stevensville

S$260

includes taxes & fees

10 Sept - 11 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

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 Garfield Center for the Arts at the Prince Theater. For more things to see and do, consider visiting Chestertown Historic District or Northern 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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Change your mind

Treat yourself

Be picky

Check availability on Chestertown Beach Resorts

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. Ramada Hotel & Conference Center by Wyndham Edgewood

5. Hampton Inn & Suites Edgewood/Aberdeen-South

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

7. Candlewood Suites Aberdeen-Bel Air by IHG

8. Kent Island Resort

Choose what matters most at beach hotels in Chestertown

Top Chestertown Hotel Reviews

Frequently asked questions

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