Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search 321,000 hotels worldwide.

Get the best price available for your trip.

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Featured Eastern Shore Hotel with a Concierge

See all 731 Hotels in Eastern Shore
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

100 Heron Blvd, Cambridge
4.0 out of 5.0
4.4 out of 5 (311 reviews)
Our room was perfectly located right off the pool but our shower was moldy/mildew, filters were lint filled and carpets had crumbs/debri on them. When we mentioned this staff quickly cleaned the bathroom while we at dinner. Then we were charged a different rate than provided on Expedia and later ...
  Oct 10, 2017

$169

$169
Great Oak Manor

Great Oak Manor

10568 Cliff Rd, Chestertown
3.5 out of 5.0
4.2 out of 5 (5 reviews)
Wonderful short winter breakWe received the warmest of welcomes and the house is a home of exquisite taste and charm in the Georgian style. We had a superb room with a Bay view, the most comfortable bed ever and the two course Breakfast included a tasty omelet with Brie and apple. All the staff were lovely and we have no hesitation ...
  Jan 31, 2017

$152

$152
Inn at 202 Dover

Inn at 202 Dover

202 East Dover Street, Easton
5.0 out of 5.0
5.0 out of 5 (5 reviews)
Fantastic place. Excellent service, awesome!!Wonderful rooms, excellent staff, great attention to detail. I highly recommend!!! Location was perfect too.
  Aug 1, 2017

$289

$289
Inn at Perry Cabin by Belmond

Inn at Perry Cabin by Belmond

308 Watkins Ln, St. Michaels
5.0 out of 5.0
4.7 out of 5 (167 reviews)
We really like the hotel. Beautiful, comfortable, clean room. Nice location, friendly staff.
  Nov 18, 2017

$293

$293
John L Stam House

John L Stam House

114 Washington Ave, Chestertown
3.0 out of 5.0
4.8 out of 5 (10 reviews)
Excellent and within walking distance of townWe had a fabulous experience at John L Stam House. From the beginning when we met our Host, to the beautiful house and grounds, yummy breakfast, to walking to town, to the minute we checked out--this visit is a must when staying in Chestertown, Maryland.
  Nov 6, 2017

$190

$190
Sandaway Waterfront Lodging Suites and Beach

Sandaway Waterfront Lodging Suites and Beach

103 West Strand Road, Oxford
3.0 out of 5.0
4.4 out of 5 (55 reviews)
Nice place, great viewsMy wife and I rode the Bellevue-Oxford ferry and Sandaway is steps from the Oxford landing. Rooms were clean and comfortable. Great Adirondack chairs on the lawn area along the waterfront, good place for a picnic and a glass of wine to the sound of the lapping waves. Breakfast is a choice of a delivered ...
  Nov 6, 2017

$279

$279
Map

Recently booked Hotel with a Concierge in Eastern Shore

Best Western Kent Narrows Inn
2.5 out of 5.0
Last booking: 3 hours ago
Best Western Plus Easton Inn & Suites
2.5 out of 5.0
Last booking: 3 hours ago
Fairfield Inn & Suites by Marriott Easton
2.5 out of 5.0
Last booking: 8 hours ago
Hyatt Regency Chesapeake Bay
4.0 out of 5.0
Last booking: 10 hours ago
Hampton Inn Easton
2.5 out of 5.0
Last booking: 11 hours ago
Comfort Inn Easton
2.5 out of 5.0
Last booking: 11 hours ago
Inn at Haven Harbour
3.0 out of 5.0
Last booking: 11 hours ago
St Michaels Inn
2.5 out of 5.0
Last booking: 15 hours ago
Sleep Inn Grasonville
2.0 out of 5.0
Last booking: 24 hours ago

Pocket Guide: Hotel with a Concierge in Eastern Shore

Search for hotels in Eastern Shore on Expedia. You can easily find your hotels in Eastern Shore using one of the methods below:

  • View our selection of featured hotels in Eastern Shore
  • Use the map to find hotels in the Eastern Shore neighborhood you prefer
  • Use the filters to see hotels in a specific area of Eastern Shore, select a specific theme, brand, or hotel class from basic (1 Star) to luxury hotels (5 Stars) in Eastern Shore
  • Enter your travel dates to view the best deals on hotels in Eastern Shore - while they last