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Our top choices for Chestertown beach hotels

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (80 reviews)
  • cleanliness
    Escape to waterfront tranquility with a private beach just 0.25 miles away, where sandy shores, volleyball courts, and loungers await.
"The private beach provides chairs and umbrellas."
United States
Ashley
The price is Rp2.293.685
Rp2.622.369 total
includes taxes & fees
6 May - 7 May
The Lodge at Great Oak Landing

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is Rp2.687.235
Rp2.982.831 total
includes taxes & fees
5 May - 6 May
Haven Point Inn and Gallery

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
8.8 out of 10, Excellent, (3 reviews)
"This is a cute little cabin. The room was as advertised. The place is also a Christian ministry place. Hotels.com guests should be aware that there are signs on the road in that reference Jesus. We also saw a couple prayer circles. This was not a problem for us. It waa early season so the lovely pools were not open. They send an email with check in directions which were use the lock box. We did not get the email. We went to what looked like a check in area and no one was around. This was quite...
United States
mary
The price is Rp6.064.786
Rp7.347.534 total
includes taxes & fees
7 May - 8 May
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
"Amazing stay great place very clean very friendly staff. Nice pool great restaurant with a wonderful bartender."
United States
David
The price is Rp3.103.323
Rp4.042.382 total
includes taxes & fees
6 May - 7 May
Kent Island Resort

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (543 reviews)
"Perfect weekend getaway for my wife’s birthday weekend. Clean, comfy, clean and plenty of outside patio’s with gas fire pits to take the evening chill away. Great Host’s. "
United States
Kevin
The price is Rp2.636.958
Rp2.953.392 total
includes taxes & fees
5 May - 6 May
Vandiver Inn

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, (591 reviews)
"Fantastic service, good breakfast, fast check in. The staff was friendly, from the front desk lady to the cleaning crew. Breakfast was basic but good and the pool was great. No towels at the pool but the front desk was quick to provide. "
United States
Luis
The price is Rp1.525.656
Rp1.708.734 total
includes taxes & fees
7 May - 8 May
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

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, (986 reviews)
"I was pleasantly surprised by how comfortable this location is. I would definitely return next time I'm in the area. Everyone I encountered was friendly and easy to talk to. The room was very clean. The continental breakfast was fresh. The breakfast area is the front desk area and very small, but well kept. It's also a good location. I was working an event that was directly across the street. There is a Weis Supermarket just down the street. And Chesapeake Bay Diner is close by with some of the...
United States
Geralyn
The price is Rp935.331
Rp1.047.571 total
includes taxes & fees
10 May - 11 May
Super 8 by Wyndham Havre De Grace Aberdeen Area
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.

Choose what matters most at beach hotels in Chestertown

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 a seasonal outdoor pool and 3 bars/lounges, 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 Northern Chesapeake Bay or 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.