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Eastern Shore, MD Luxury Hotels

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Eastern Shore Hotels

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Top Eastern Shore Neighborhoods for Luxury Hotels

Easton
5 hotels

Inn at 202 Dover

5.0 out of 5.0
from

$246

Grasonville
3 hotels
from

$105

St. Michaels
2 hotels
from

$390

Featured Eastern Shore Luxury Hotels

See all 450 Hotels in Eastern Shore
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
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
Holiday Inn Express Cambridge

Holiday Inn Express Cambridge

2715 Ocean Gtwy, Cambridge
2.5 out of 5.0
4.0 out of 5 (53 reviews)
Great lodging for mini stay. Wonderful beds Well received and very customer friendly with all needs meet
  Jul 5, 2017

$109

$109
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
St Michaels Inn

St Michaels Inn

1228 S Talbot Street, St. Michaels
2.5 out of 5.0
3.6 out of 5 (87 reviews)
Close enough to activities Hotel was deceivingly big. It was clean, good size room and staff was very helpful
  Jul 23, 2017

$101

$101
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
Days Inn Easton

Days Inn Easton

7018 Ocean Gateway, Easton
1.5 out of 5.0
2.2 out of 5 (16 reviews)
Economy blissEverything was clean, staff was GREAT! Affordable. Made our family vacation a wonderful one.
  Jul 11, 2017

$63

$63
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

100 Heron Blvd, Cambridge
4.0 out of 5.0
4.3 out of 5 (99 reviews)
Great place for families but priceyWe had the club floor which was great however the staff there was not friendly and seemed mad if you asked them for something. Not too much variety. We are at the library very basic food, took the shuttle to the marina restaurant very good. Too much money but a great place
  Jul 19, 2017

$249

$249
Holiday Inn Express Annapolis - Kent Island

Holiday Inn Express Annapolis - Kent Island

1020 Kent Narrows Rd, Grasonville
2.5 out of 5.0
4.2 out of 5 (60 reviews)
Bay viewThis hotel is great from top to bottom . The staff is helpful. Breakfast is good . We enjoy sitting out on the deck and viewing the bay
  Jun 30, 2017

$122

$122
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

3101 Main Street, Grasonville
2.5 out of 5.0
3.4 out of 5 (74 reviews)
Great place to stayEasy access to Rt 50. Clean, comfortable & wonderful staff especially Mr. Tim. Very good breakfast, more than just coffee & bagels.
  Jul 23, 2017

$105

$105
Map

Recently booked Eastern Shore hotels

Holiday Inn Express Hotel & Suites Chestertown
2.5 out of 5.0
Last booking: 2 hours ago
Fairfield Inn & Suites by Marriott Easton
2.5 out of 5.0
Last booking: 3 hours ago
Days Inn & Suites Cambridge
2.0 out of 5.0
Last booking: 4 hours ago
Days Inn Easton
1.5 out of 5.0
Last booking: 4 hours ago
Hyatt Regency Chesapeake Bay
4.0 out of 5.0
Last booking: 6 hours ago
Holiday Inn Express Easton
2.5 out of 5.0
Last booking: 6 hours ago
Best Western Kent Narrows Inn
2.5 out of 5.0
Last booking: 8 hours ago
Hilton Garden Inn Kent Island
3.0 out of 5.0
Last booking: 10 hours ago
The Tidewater Inn
3.0 out of 5.0
Last booking: 14 hours ago

A weekend away keeps your troubles at bay, so book your ticket to Eastern Shore and get ready to relax. Fascinating attractions, exquisite eats, and some of the world’s most stunning photo opportunities: these are just some of the reasons to take a trip to Eastern Shore. You'll treat yourself to decadent meals, eye-guzzle the most popular points of interest , and snag seats to the most popular performances. Of course, you'll stay at a luxury hotel! Extravagant experiences are right up your alley, so get your upscale hotel in Eastern Shore on Expedia.com today and start your excursion off on the right (well-dressed) foot.

5-Star Vacations in Eastern Shore

It turns out plenty of folks love Eastern Shore enough to call it home -- how is that for proof that Eastern Shore is full of an incredible assortment of activities? Whether you’re looking to spend your vacation dining on the best regional fare or browsing art galleries in Eastern Shore, you'll never be disappointed. Eastern Shore is full of great hotels in addition to friendly locals, so you can count on a marvelous stay. Book early to get the best room!

A luxury retreat begs for you to explore day spas, art, and local museums. When you save big by booking on Expedia.com, it's all at your fingertips. Thanks to our incredible rates on hotels, you'll still have money in your budget for the most fun and free-spirited adventures. After many hours of exploring the city, your luxury hotel is waiting with fine dining and impressive amenities. Take advantage of amenities like an oversized bathtub or indoor pool before the day is through. The luxury accommodations in Eastern Shore will have you basking in serenity as soon as you check in.

Luxury Eastern Shore Hotels

When you’ve got your heart set on making the most of your luxurious getaway in Eastern Shore, Expedia.com is here to save the day. Browse the wealth of ratings and reviews on more than a dozen hotels to find an accommodation that suits your needs. 5-Star hotels treat you right, offering things like VIP services and private fireplaces. Some of the city's 5-star accommodations even feature gigantic penthouses, while others have tennis courts or salt water pools. Use our mobile booking app to find and book a fabulous 5-star hotel in Eastern Shore, and prepare for the experience of a lifetime!