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Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

Tonight
28 Oct - 29 Oct
Tomorrow
29 Oct - 30 Oct
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Top Chestertown Beach Hotels

Lobby
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (835)
"The thermostat controls were easy to adjust. Night desk lady was friendly and pleasant. "
United States
Charlie
The price is AED 375
AED 416 total
includes taxes & fees
30 Oct - 31 Oct
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (409)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
United States
Cynthia
The price is AED 298
AED 330 total
includes taxes & fees
3 Nov - 4 Nov
Red Roof Inn & Suites Chestertown
Front of property - evening/night
Driftwood Inn
Driftwood Inn
2.0 star property
5.2 out of 10, (174)
"Rooms are clean, staf was helpful "
United States
Daryl
Driftwood Inn
Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
3.5 star property
7.8 out of 10, Good, (72)
"For the price off season the room should have had better amenities "
United States
Daniel
The price is AED 486
AED 556 total
includes taxes & fees
29 Oct - 30 Oct
The Lodge at Great Oak Landing
Property grounds
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (105)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
United States
Mary
The price is AED 331
AED 547 total
includes taxes & fees
29 Oct - 30 Oct
First Floor Studio Apartment in Historic Chestertown
Terrace/patio
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, (85)
"Everything we needed was there. Owners next sore are super nice and hrphful."
United States
steven s.
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Exterior
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
9.8 out of 10, Exceptional, (23)
"We had a great time"
United States
Harold L.
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (61)
"Great!"
United States
Shaama P.
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Fridge, microwave, oven, stovetop
Country Estate in Historic District
Country Estate in Historic District
10.0 out of 10, Exceptional, (70)
"Great hosts, location, gardens, and overallstay! "
United States
Robin G.
Country Estate in Historic District
On the beach, sun loungers
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
10.0 out of 10, Exceptional, (83)
"One of our favorite spots! Never disappoints."
United States
victoria g.
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
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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Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Everything was great - the beds and pillows are very comfortable, room very clean and breakfast was decent and staff very friendly. "
Charles 1-night trip
Posted 8 days ago
Comfort Inn & Suites Chestertown

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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.
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 Main Beach 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.