Photo by Assya A

Find Resorts & Hotels with Spas in Chestertown, MD

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Resorts & Hotels with Spas

Tonight
24 Aug - 25 Aug
Tomorrow
25 Aug - 26 Aug
Next weekend
29 Aug - 31 Aug
In two weeks
5 Sep - 7 Sep

Top Chestertown Resorts & Hotels with Spas

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (800)
"Very clean. Very professional staff. Loved the free breakfast."
The price is SAR 411
SAR 457 total
includes taxes & fees
7 Sep - 8 Sep
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, (387)
"Good location."
The price is SAR 287
SAR 319 total
includes taxes & fees
1 Sep - 2 Sep
Red Roof Inn & Suites Chestertown
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (98)
"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
25 Aug - 26 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
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Property grounds

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (73)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown 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!
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
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
TV, fireplace

Langford Creek Estate | Waterfront w/ HOT TUB + Deck!

9.2 out of 10, Wonderful, (5)
"Such a great house and wonderful location. Highly recommend!"
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
Terrace/patio

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

10.0 out of 10, Exceptional, (24)
"had a great time "
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
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

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

10/10 Excellent
"Thank you for such a great stay for my bday "
Fatima 1-night trip
Posted 3 days ago
Sagamore Pendry Baltimore