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Beach Hotels & Resorts in Chestertown from AU$139

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Check availability on Chestertown Beach Hotels

Best Chestertown Beach Hotels

Lobby
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (834)
"The thermostat controls were easy to adjust. Night desk lady was friendly and pleasant. "
United States
Charlie
The price is AU$174
includes taxes & fees
28 Oct - 29 Oct
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (406)
"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 AU$139
includes taxes & fees
29 Oct - 30 Oct
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 AU$233
includes taxes & fees
26 Oct - 27 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 AU$247
includes taxes & fees
28 Oct - 29 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, (84)
"We had a wonderful weekend. Thank you!"
United States
Stephen H.
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

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.