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Historic Eastern Shore, MD Hotels

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Top Eastern Shore Neighborhoods for Historic Hotels

St. Michaels
2 hotels
from

$390

Easton
9 hotels

The Tidewater Inn

3.0 out of 5.0
from

$149

Chestertown
1 hotels

Quality Suites

2.5 out of 5.0

Featured Eastern Shore Historic Hotels

See all 450 Hotels in Eastern Shore
The Albanus Phillips Inn

The Albanus Phillips Inn

314 Mill Street, Cambridge
3.0 out of 5.0
4.2 out of 5 (5 reviews)
Just passing through town.What a beautiful old house. I made a reservation through Expedia the morning before getting there and apparently no one had checked to realize I was coming, but we got that worked out and it was a delightful stay. Huge comfortable room, large (really large) bathroom. I was the only person staying ...
  Nov 9, 2016

$155

$155
The Tidewater Inn

The Tidewater Inn

101 E Dover St, Easton
3.0 out of 5.0
4.2 out of 5 (116 reviews)
Quaint and Great LocationRoom was very nice in a quaint hotel. Eateries and shops within walking distance.
  Jul 11, 2017

$149

$149
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

8708 Alicia Drive, Easton
2.5 out of 5.0
4.8 out of 5 (124 reviews)
Very good value!The hotel is clean, has good amenities: pool, small gym, breakfast included. We were two adults and two children and all stayed comfortably in a kind suite with a sofa bed. It's located just outside Easton with easy access to surrounding towns. It doesn't have the charm of a B & B but you can't the ...
  Jul 15, 2017

$110

$110
Five Gables Inn and Spa

Five Gables Inn and Spa

209 N. Talbot Street, St. Michaels
3.5 out of 5.0
4.2 out of 5 (39 reviews)
Nice hotel/bed and breakfast close to everything.After we had a small problem with our room, we were moved to another room quickly without any hassle. The room was comfortable and spacious and the breakfast was delicious. The muffins were incredible.
  Sep 22, 2016

$195

$195
Inn at Perry Cabin by Belmond

Inn at Perry Cabin by Belmond

308 Watkins Ln, St. Michaels
4.5 out of 5.0
4.7 out of 5 (59 reviews)
Quiet get-awayLovely grounds. Greeted by lovely upbeat young men who were always politely at your service. Perfect...
  Jul 21, 2017

$390

$390
Holiday Inn Express Easton

Holiday Inn Express Easton

8561 Ocean Gateway Route 50, Easton
2.5 out of 5.0
4.3 out of 5 (43 reviews)
Easy access to destinations. Great free breakfasts, friendly staff and clean, comfortable rooms. Great location to many destinations on our vacation.
  Jul 9, 2017

$94

$94
Lazyjack Inn on Dogwood Harbor

Lazyjack Inn on Dogwood Harbor

5907 Tilghman Island Road, Tilghman
3.5 out of 5.0
5.0 out of 5 (16 reviews)
gracious hosts & charming accomodationsVery gracious husband/wife owners. Engage guests in conversation, but not TOO much. LOVELY breakfast--not your run-of-the-mill fare..very creative & delicious. Definitely an excellent value
  Nov 14, 2016

$185

$185
Inn at 202 Dover

Inn at 202 Dover

202 East Dover Street, Easton
5.0 out of 5.0
5.0 out of 5 (1 reviews)
Fantastic accommodation's and staff. I would highly recommend this establishment to anyone. The Owners were very hospitable. Our meal in the Peacock Dining room was out of this world. The Chef is in a league of his own!
  Aug 5, 2016

$246

$246
Sandaway Waterfront Lodging

Sandaway Waterfront Lodging

103 West Strand Road, Oxford
3.0 out of 5.0
4.3 out of 5 (15 reviews)
Peaceful getawayWe wanted to find peace and quiet with water views and Sandaway was perfect! We enjoyed sitting out on Adirondack chairs gazing at the passing sailboats. Room was clean and comfortable with vintage character and loved sitting in our private screened in porch.
  Jun 4, 2017

$279

$279
Robert Morris Inn - A Waterfront Country Inn

Robert Morris Inn - A Waterfront Country Inn

314 N. Morris St, Oxford
3.0 out of 5.0
4.1 out of 5 (27 reviews)
Historic Inn Great CharmLoved it ,charming little town right on the water. Staff super nice and the food AMAZING we had both dinner and breakfast . FANTASTIC every bite was delicious can't wait to dine here again . Lucky for us it is only an hour from our home .
  Jul 22, 2017

$175

$175
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Recently booked Eastern Shore hotels

Comfort Inn & Suites Cambridge
2.0 out of 5.0
Last booking: 2 hours ago
Days Inn & Suites Cambridge
2.0 out of 5.0
Last booking: 2 hours ago
Americas Best Value Inn
2.0 out of 5.0
Last booking: 2 hours ago
Holiday Inn Express Cambridge
2.5 out of 5.0
Last booking: 6 hours ago
Fairfield Inn & Suites by Marriott Easton
2.5 out of 5.0
Last booking: 7 hours ago
Econo Lodge Easton
1.5 out of 5.0
Last booking: 9 hours ago
Days Inn Easton
1.5 out of 5.0
Last booking: 9 hours ago
Hyatt Regency Chesapeake Bay
4.0 out of 5.0
Last booking: 10 hours ago
Holiday Inn Express Easton
2.5 out of 5.0
Last booking: 10 hours ago

Historic Eastern Shore Hotels Information

Travel back in time and reserve a room at a historic Eastern Shore hotel.
  • Choose from our vast selection of historic hotels in Eastern Shore
  • Stay in a classic hotel with intriguing antiquity
  • Don’t waste time searching for lower prices elsewhere

Book today and experience the heritage and allure of a hotel with a story and a past. Look past the sparkly, high-rise hotels and go the rustic route instead.

Because when you choose a historic Eastern Shore hotel with a story to tell, you’ll have your own tales to share when you go back home. We doubt those brand new high-rises have that kind of charisma! Older accommodations have a colorful past, and many are located at the site of a significant event. These fascinating relics offer a glimpse into a different era and way of life. During your stay at a historical hotel in Eastern Shore, marvel at the on-site antiques and explore the nearby landmarks. You’ll feel as though you traveled through time as you take a tour of the area and other historical attractions during your vacation.

While we can’t offer you the same hotel rates of yesteryear, we can present you with the lowest prices on the market today. Thanks to our great prices, you can confidentially book classic historic Eastern Shore hotels knowing you won’t find a better discount elsewhere. Whether you’re a history buff wanting to brush up on your facts or a jetsetter looking for a famous place to rest, browse our selection of historic Eastern Shore hotels. Make your reservations today and put the cash you saved toward stocking up on antique souvenirs, artifacts, and artwork.