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Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

Tonight
27 Jul - 28 Jul
Tomorrow
28 Jul - 29 Jul
Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug

Top Chestertown Beach Hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (787)
"Great stay. Sorry pool was closed "
Anita
The price is SAR 429
SAR 477 total
includes taxes & fees
17 Aug - 18 Aug
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (381)
"good price, convenient. pool was closed which was disappointing."
charlene
The price is SAR 287
SAR 319 total
includes taxes & fees
3 Aug - 4 Aug
Red Roof Inn & Suites Chestertown
Driftwood Inn
Front of property - evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
Quiana
The price is SAR 238
SAR 264 total
includes taxes & fees
28 Jul - 29 Jul
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, (55)
"The room was very clean and comfortable. No frills but perfect for our overnight stay. The view from the queen bed room was lovely. The waitress at the restaurant was exceptional and the food was delicious and hot. We enjoyed the private
beach
and the areas to walk around the marina."
Anonymous traveler
The price is SAR 484
SAR 537 total
includes taxes & fees
29 Jul - 30 Jul
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, (91)
"Loved the backyard view onto the golf course."
Karen
The price is SAR 371
SAR 596 total
includes taxes & fees
4 Aug - 5 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)
"We had a lovely stay at this cottage on the water. The cottage had its own dock, deck, mini
beach
, grassy yard with kayaks, paddle boat, stand up paddles —enough for everyone. The birding is brilliant. The hosts have created an environment that welcomes birds. On our morning paddle, we saw bald eagles, ample herons, other
sea
birds and an otter, snakes and turtles. The house has everything you need. It’s very comfortable with a full kitchen, games, plenty of different spaces to relax and...
Maureen H.
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)
"Stayed here for 3 nights with our extended family (six adults, one toddler, one infant, and dog). We were very comfortable and appreciated the layout of the house as it allowed us to keep our family with young children somewhat separated from the noise when they went to bed before the others. Our daughter swam in the river everyday (definitely bring water shoes at it is very rocky in the water and some glass washes up on the
beach
) and played with her sand toys. Our dog ran freely without...
Amanda B.
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Country Estate in Historic District
Fridge, microwave, oven, stovetop

Country Estate in Historic District

10.0 out of 10, Exceptional, (69)
"A lovely home and amenities. We had a winderful stay."
Susan N.
Country Estate in Historic District
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)
"The house was perfect for a multi-generational family reunion. The house was clean, and the kitchen, bedrooms and bathrooms had everything we needed for our stay. The property manager was very helpful and easy to contact with questions. We enjoyed the water and
beach
and walking to Chestertown."
Helen C.
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Contemporary waterfront house with private dock & kayaks!
Exterior

Contemporary waterfront house with private dock & kayaks!

10.0 out of 10, Exceptional, (66)
"Spent an enjoyable long weekend in this lovely house with great views of the water from every room. We made good use of the kayaks paddling out to the bay and back fishing along the way. The check in process was quick and John was, as others have mentioned, very responsive to any questions. The kitchen did not lack anything we needed and the wi-fi signal was good. We enjoyed our time there."
Jack M.
Contemporary waterfront house with private dock & kayaks!
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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Great Experience !! "
James 3-night trip
Posted 5 days ago
Hilton Garden Inn Kent Island Marina
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Service was great all the staff we came in contact with were kind and helpful from showing us how to work the TV to giving us bottled water when the drink vending machine was out. We enjoyed our stay and the location was very close to Chestertown and Rock Hall."
Anonymous traveler 2-night trip
Posted 9 days ago
Comfort Inn & Suites Chestertown

Frequently asked questions

What is Chestertown like for travelers who love the beach?
Known for its university life, Chestertown offers a lot for the traveler planning a getaway.
What's the best hotel for a beach vacation 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.
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 vacation in Chestertown?
You can plan your beach trip with this snapshot of the seasons in Chestertown: The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
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 like 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 center. If you'd like to venture out around the area, you may want a rental car for your journey.