Search Beach Resorts & Hotels in Chestertown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Beach Resorts & 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
3.5 star property
Chestertown
8.0 out of 10, Very good, (81 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 ฿4,288
฿4,902 total
includes taxes & fees
18 May - 19 May
The Lodge at Great Oak Landing
Exterior

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is ฿5,023
฿5,576 total
includes taxes & fees
19 May - 20 May
Haven Point Inn and Gallery
Exterior

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 ฿11,337
฿13,735 total
includes taxes & fees
21 May - 22 May
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
Reception

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 ฿4,836
฿6,469 total
includes taxes & fees
26 May - 27 May
Kent Island Resort
Exterior detail

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 ฿4,929
฿5,521 total
includes taxes & fees
27 May - 28 May
Vandiver Inn
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.
View all properties

Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included

Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Plenty of parking, various items for breakfast, family friendly, close to many location "
Celina 1-night trip
Posted 4 days ago
Comfort Inn & Suites Chestertown

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 Rolphs Wharf Marina. 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.