Photo by Assya A

Find Beach Resorts in Chestertown, MD

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Beach Resorts & Hotels

Top Chestertown Beach Resorts & Hotels

Our top choices for Chestertown beach hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (797)
"It was a clean comfortable spot to rest for the night. "
The price is £90
includes taxes & fees
7 Sept - 8 Sept
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout curtains

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (386)
"Good location."
The price is £59
includes taxes & fees
27 Aug - 28 Aug
Red Roof Inn & Suites Chestertown
Driftwood Inn
Front of property – evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (172)
"Rooms are clean, staf was helpful "
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
8.0 out of 10, Very good, (65)
"Great place to get some quiet rest by the water"
The price is £109
includes taxes & fees
26 Aug - 27 Aug
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, (98)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is £121
includes taxes & fees
25 Aug - 26 Aug
First Floor Studio Apartment in Historic Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Terrace/patio

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

9.8 out of 10, Exceptional, (83)
"Loved the location next to the river. Spent a lot of time on the dock and in the yard. Proximity to Chestertown a real plus too. Great hosts!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
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, (81)
"Loved our stay!"
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)
"We had a great time"
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Country Estate in Historic District
Fridge, microwave, oven, stovetop

Country Estate in Historic District

10.0 out of 10, Exceptional, (69)
"Beautiful kitchen so whole family could cook dinner together Friday night before soiree at Brittland Manor. Patio out back, perfect for sipping coffee and chatting. Close to town, lots of places to walk to - including farmer's market and the college."
Country Estate in Historic District
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Outdoor pool

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
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.

Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"FEELS LIKE PEACEFULLY 👍 👌 "
Brian 4-night trip
Posted 7 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 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.