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Check availability on Chestertown Beach Resorts & Hotels

Top Chestertown Beach Resorts & Hotels

Our top choices for Chestertown beach hotels

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (804)
"Friendly staff, clean room, convenient location. "
The price is £90
includes taxes & fees
7 Sept - 8 Sept
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (388)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is £63
includes taxes & fees
7 Sept - 8 Sept
Red Roof Inn & Suites Chestertown

Driftwood Inn

2.0 star property
5.2 out of 10, (174)
"Rooms are clean, staf was helpful "
Driftwood Inn

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (66)
"Great place to get some quiet rest by the water"
The price is £109
includes taxes & fees
8 Sept - 9 Sept
The Lodge at Great Oak Landing

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (99)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is £114
includes taxes & fees
28 Aug - 29 Aug
First Floor Studio Apartment in Historic Chestertown

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

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

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!

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

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.

Find out more about Chestertown

Find out more about Chestertown

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