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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
Lobby

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
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, (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
Front of property – evening/night

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
Private beach nearby, sun-loungers, beach volleyball

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
Property grounds

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
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
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
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!
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.

Find out more about Chestertown

Find out more about Chestertown

Popular beach getaways

Most booked beach stays in Chestertown in 2025

Kid-friendly beach stays in Chestertown
Kid-friendly beach stays
Kid-friendly beach stays
Hotels with pools in Chestertown
Hotels with pools
Hotels with pools

Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Check in/out went smoothly. Room was big and comfortable. Low pressure in shower."
Linda 2-night trip
Posted 4 days ago
Comfort Inn & Suites Chestertown

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