Photo by Assya A

Chestertown Hotel Guide - Beach Hotels in Chestertown, Maryland

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Check availability on Chestertown Beach Hotels

Top Chestertown Beach Hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (748)
"It was fine and served our needs."
The price is €101
includes taxes & fees
3 Apr - 4 Apr
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (335)
"This property was def. Off season. It was very low key, the room was big and clean, hotel understaffed but I think it was just the time of year. Overall would for sure stay here again.Big value for the cost"
The price is €57
includes taxes & fees
18 Mar - 19 Mar
Red Roof Inn & Suites Chestertown
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
5.0 out of 10, (167)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is €65
includes taxes & fees
19 Mar - 20 Mar
Driftwood Inn
The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (46)
"Generally okay, Clean but property could use some upgrade"
The price is €110
includes taxes & fees
26 Mar - 27 Mar
The Lodge at Great Oak Landing
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (79)
"This property is located in a excellent neighborhood overlooking a golf course and a short distance to the Chester river. The room was immaculate and ideal for all ages, especially Senior citizens. We booked this room for our 67th wedding anniversary in the first week in February with unfavorable weather, but the room was very cozy. We will defiently return later this year."
The price is €149
includes taxes & fees
26 Mar - 27 Mar
First Floor Studio Apartment in Historic Chestertown
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
Property grounds

Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

10.0 out of 10, Exceptional, (5)
"So delightful"
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Terrace/patio

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (75)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Exterior

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

9.8 out of 10, Exceptional, (22)
"Perfect spot for our whole family to be together. It has it all. Everything worked. Super comfy. Thank you!!!!"
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (80)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Country Estate in Historic District
Fridge, microwave, oven, stovetop

Country Estate in Historic District

10.0 out of 10, Exceptional, (66)
"Wow! This house is beautiful. A gem of old and new areas with lovely finishes and lots of space, each of us four guests had our own bedroom. The owners have supplied this domicile with every amenity one could imagine. It was well stocked with towels, paper products, kitchen tools and wonderful appliances. On the island stood a welcoming bottle of wine. Having enjoyed our stay so much, We may be returning next year! "
Country Estate in Historic District
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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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 .
How many beach hotels are there in Chestertown?
Expedia has 6 beach hotels in Chestertown that are great for your beachside getaway.
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 Earle Landing 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 Historical Society of Kent County Maryland 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.