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

Chestertown Hotel Guide - Beach Hotels in Chestertown, Maryland

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Check availability on Chestertown Beach Hotels

Our top choices for Chestertown beach hotels

Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
8.0 out of 10, Very good, (91 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 €132
includes taxes & fees
20 Jul - 21 Jul
The Lodge at Great Oak Landing
Property amenity

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (1,003 reviews)
The price is €54
includes taxes & fees
20 Jul - 21 Jul
Super 8 by Wyndham Havre De Grace Aberdeen Area
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (159 reviews)
The price is €173
includes taxes & fees
29 Jul - 30 Jul
Kent Island Resort
Fridge, microwave

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (510 reviews)
The price is €83
includes taxes & fees
16 Jul - 17 Jul
Village Inn Annapolis MD
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (559 reviews)
The price is €142
includes taxes & fees
21 Jul - 22 Jul
Vandiver Inn
Free daily continental breakfast

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, (618 reviews)
The price is €92
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,910 reviews)
The price is €126
includes taxes & fees
22 Jul - 23 Jul
Historic Inns of Annapolis
Superior Room, 1 King Bed (Smoke Free)

Red Roof Inn Aberdeen

Red Roof Inn Aberdeen
2.0 star property
Aberdeen
6.4 out of 10, (1,001 reviews)
The price is €54
includes taxes & fees
19 Jul - 20 Jul
Red Roof Inn Aberdeen
Terrace/patio

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, (388 reviews)
The price is €96
includes taxes & fees
10 Aug - 11 Aug
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Combined shower/bathtub, free toiletries, hair dryer, towels

Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
2.0 star property
Edgewood
6.6 out of 10, (548 reviews)
The price is €88
includes taxes & fees
20 Jul - 21 Jul
Ramada Hotel & Conference Center by Wyndham Edgewood
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

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

8/10 Good
"The location was absolutely stunning, I honestly loved the dock and pool in the back. The building could use some repairs and upgrades but honestly didn’t take away from the experience. The breakfast was great too!"
Shannon 1-night trip
Posted 5 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG

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 a seasonal outdoor pool and free WiFi, and it's located near a private 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 Chestertown Historic District or Rolphs Wharf Marina.
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.