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Featured Eastern Shore Adventure Hotels

See all 563 Hotels in Eastern Shore
Black Walnut Point Inn

Black Walnut Point Inn

4417 Black Walnut Point Road, Tilghman
3.5 out of 5.0
4.1 out of 5 (7 reviews)
Quaint GetawayNice getaway prior to our meeting the next day at Philips Wharf Environmental Center. Would love to spend more time here.
  Mar 14, 2017

$132

$132
Chesapeake House Tilghman Island

Chesapeake House Tilghman Island

21551 Chesapeake House Drive, Tilghman
3.0 out of 5.0
2.7 out of 5 (10 reviews)
Duck hunting from TilghmanVery accomodating, had a very late check in. Great views from room. Very friendly staff. Great fishermans breakfast very early morning.
  Jan 17, 2017

$77

$77
George Brooks House B&B

George Brooks House B&B

24500 Rolles Range Road, St. Michaels
3.0 out of 5.0

$190

$190
Great Oak Manor

Great Oak Manor

10568 Cliff Rd, Chestertown
3.5 out of 5.0
5.0 out of 5 (1 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

$172

$172
Hampton Inn Easton

Hampton Inn Easton

8058 Ocean Gateway, Easton
2.5 out of 5.0
4.6 out of 5 (47 reviews)
Eric at the front deskThis young man completely made my stay. He- hands down- is the reason I would return. Friendly, good eye contact, genuine...... Couldn't ask for anyone better. He should be promoted within the organization!
  Aug 21, 2017

$129

$129
Harbourtowne St. Michaels

Harbourtowne St. Michaels

9784 Martingham Circle, St. Michaels
3.0 out of 5.0
3.9 out of 5 (67 reviews)
Pleasant propoerty on the waterPleasant stay, though a bit windy there on the water. Refrigerator and microwave convenient but the freezer worked very poorly despite rapid response from maintenance when queried. Spacious sitting room and bedroom with good king size bed in the suite. Second floor location with no elevator created ...
  Dec 12, 2016
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 (64 reviews)
Good for a quick staySpent 1 night at this hotel for a wedding. Thankfully, the hotel was not fully booked and the very friendly and accommodating staff we're able to afford me an early check-in. Room was comfortable - my only complaint was that I woke up to find a huge cockroach on my bathroom floor which made me wonder ...
  Sep 13, 2017

$130

$130
Lowes Wharf Marina Inn

Lowes Wharf Marina Inn

21651 Lowes Wharf Rd, Sherwood
3.0 out of 5.0
3.2 out of 5 (4 reviews)
Labor Day weekend getawayIt was our first visit here. Wanted a cool spot not too far from DC. Small and intimate like I like it. Daytime was busy with lots more visitors. Night was beautiful with nice sunsets and few people. Ate one meal that was really delicious.
 Tony Oct 16, 2013

$169

$169
Miles River Guest House

Miles River Guest House

8862 Quailsar Road, Easton
3.5 out of 5.0
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Recently booked Adventure Hotels in Eastern Shore

Hilton Garden Inn Kent Island
3.0 out of 5.0
Last booking: 8 hours ago
Hyatt Regency Chesapeake Bay
4.0 out of 5.0
Last booking: 11 hours ago
Knapps Narrows Marina & Inn
3.0 out of 5.0
Last booking: 12 hours ago
Best Western Kent Narrows Inn
2.5 out of 5.0
Last booking: 12 hours ago
Best Western Denton Inn
2.5 out of 5.0
Last booking: 14 hours ago
Hampton Inn Easton
2.5 out of 5.0
Last booking: 15 hours ago
The Tidewater Inn
3.0 out of 5.0
Last booking: 15 hours ago
Driftwood Inn
2.0 out of 5.0
Last booking: 15 hours ago
Days Inn Easton
1.5 out of 5.0
Last booking: 16 hours ago

Eastern Shore Adventure Hotel Guide

Buckle up for the thrill of a lifetime when you book an adventure hotel in Eastern Shore.
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Book with Expedia.com today and rest assured you’ve landed the best rates around. Because you should take a leap of faith on your activities and not your accommodations.

However, adventure travel isn’t purely for thrill-seeking tourists anymore. Thanks to adventure hotels in Eastern Shore, you can take off on an eye-opening journey near the region’s most picturesque locales--even if you simply want to bask in the beauty of the outdoors. Of course, there’s plenty to keep adrenaline-loving adventurers occupied, too. Whether you’re into extreme action sports or calmer sightseeing trips, our selection of Eastern Shore adventure hotels lets you experience it all nearby. Book an accommodation today, and challenge yourself to gravity-defying activities and exotic excursions tomorrow.

After a day of heart-racing events, unwind with some of the best amenities in town. From clean and comfortable rooms to on-site restaurants and bars, our adventure hotels offer the ideal balance of bold activities and chilled-out atmospheres. Here at Expedia, we feature the lowest rates around certain to get your adrenaline rushing. Browse our adventure resorts in Eastern Shore and score cheap deals, so you can spend more on your excursions and less on your accommodations.