Photo by Assya A

Search Hotels with Entertainment in Chestertown

    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 Hotels with Entertainment

Top Chestertown Hotels with Entertainment

Travelodge by Wyndham Aberdeen
Enjoy meals in a spacious dining area with comfortable seating and large windows offering views of the surrounding greenery.

Travelodge by Wyndham Aberdeen

2.0 star property
6.2 out of 10, (500)
"Great location "
The price is 1.746.319 ₫
1.955.877 ₫ total
includes taxes & fees
11 Aug - 12 Aug
Travelodge by Wyndham Aberdeen
Annapolis Waterfront Hotel, Autograph Collection
Relax in this serene room with a large bed, a comfortable armchair, and a floor lamp, offering a view of the nearby water.

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (853)
" Very clean, spacious room, friendly staff"
The price is 6.218.310 ₫
7.088.874 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Annapolis Waterfront Hotel, Autograph Collection
Flag House Inn
Stunning two-story home with a charming porch and symmetrical facade, featuring a central entrance and evenly spaced windows.

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (73)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
The price is 3.657.830 ₫
4.169.926 ₫ total
includes taxes & fees
11 Aug - 12 Aug
Flag House Inn
Historic Inns of Annapolis
Relax in the serene outdoor patio, surrounded by trees and equipped with comfortable seating and tables.

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1822)
"We’ve been here a few times and continue to to love the location, staff and comfortable beds. "
Historic Inns of Annapolis
86 State Circle - Luxury Boutique Hotel
Stroll through the charming streets, lined with historic architecture and vibrant autumn foliage.

86 State Circle - Luxury Boutique Hotel

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is 7.732.573 ₫
8.815.134 ₫ total
includes taxes & fees
12 Aug - 13 Aug
86 State Circle - Luxury Boutique Hotel
Home2 Suites by Hilton Baltimore/White Marsh
Relax in the hotel's outdoor patio area, featuring tables, chairs, and a fire pit surrounded by comfortable seating.

Home2 Suites by Hilton Baltimore/White Marsh

3.0 star property
8.0 out of 10, Very good, (1000)
"I really enjoyed my stay "
The price is 2.875.133 ₫
3.320.779 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Home2 Suites by Hilton Baltimore/White Marsh
WoodSpring Suites Baltimore White Marsh - Nottingham
Relax in a comfortable living area with a sofa, wooden bench, and dining space.

WoodSpring Suites Baltimore White Marsh - Nottingham

2.5 star property
5.8 out of 10, (1000)
"The cleanliness "
The price is 2.202.564 ₫
2.543.961 ₫ total
includes taxes & fees
11 Aug - 12 Aug
WoodSpring Suites Baltimore White Marsh - Nottingham
Sagamore Pendry Baltimore
Enjoy waterfront views from this property's central pool, situated on a man-made dock with access to the water.

Sagamore Pendry Baltimore

5.0 star property
9.4 out of 10, Exceptional, (1004)
"Beautiful, professional establishment. "
The price is 9.544.444 ₫
12.293.192 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Sagamore Pendry Baltimore
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