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Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

Top Chestertown Beach 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, (816)
"Friendly staff, clean room, convenient location. "
The price is SAR 443
SAR 491 total
includes taxes & fees
7 Oct - 8 Oct
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, (395)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is SAR 287
SAR 319 total
includes taxes & fees
22 Sep - 23 Sep
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 "
The price is SAR 238
SAR 264 total
includes taxes & fees
14 Oct - 15 Oct
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, (68)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
The price is SAR 441
SAR 490 total
includes taxes & fees
18 Sep - 19 Sep
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, (100)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is SAR 371
SAR 596 total
includes taxes & fees
22 Sep - 23 Sep
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, (84)
"We had a wonderful weekend. Thank you!"
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
Country Estate in Historic District
Fridge, microwave, oven, stovetop

Country Estate in Historic District

10.0 out of 10, Exceptional, (69)
"Great hosts, location, gardens, and overallstay! "
Country Estate in Historic District
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
On the beach, sun loungers

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (81)
"This home on the Chester River exceeded expectations. It was super clean, bright & roomy. It had great sleeping options for a 7-person group of women. The backyard up against the river was terrific. The water was so still for kayaking. There are multiple seating areas: fire pit, table on the pier, table off of the patio. The screened in patio was wonderful to use. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
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.

Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"We came here for a birthday weekend away with our family of 6. From the minute we got there we were greeted by this very sweet girl, Amber. She was very friendly and got us everything we needed without even being asked including the extra sheets for the pull out and getting a big cart for us. The room was very clean and breakfast was delicious. We will definitely be back. "
Kristina 2-night trip
Posted 1 day ago
Comfort Inn & Suites Chestertown

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