Eastern Shore Holiday Homes

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Check availability on Holiday Homes in Eastern Shore

18 Dec - 19 Dec

Tonight

19 Dec - 20 Dec

Tomorrow night

Featured Holiday Homes in Eastern Shore

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

Ocean City MD

CHF 248

22 Dec - 23 Dec

includes taxes & fees

During your stay at this holiday home, you're just a quick walk from Ocean City Beach. Enjoy features like an outdoor pool, a water park and laundry facilities. The holiday home offers a kitchen and 3.5 bathrooms.

Pool

Küche

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Perryville MD

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During your stay at this holiday home, you're just a quick walk from Chesapeake Bay. A water park, 1 hot tub and laundry facilities are available. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.

Whirlpool

Küche

"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

Ocean City MD

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During your stay at this holiday home, you're just a quick walk from Ocean City Beach. You'll find features such as free WiFi in public areas, plus an outdoor pool and a water park. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.

Pool

Küche

BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!

Ocean City MD

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During your stay at this holiday home, you're just a quick walk from Ocean City Beach. Free WiFi in public areas, a water park and laundry facilities are available. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.

Küche

Waschmaschine

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge MD

CHF 275

12 Jan - 13 Jan 2026

includes taxes & fees

During your stay at this holiday home, you're just a quick walk from Long Wharf Park. You'll find features such as breakfast (surcharge) and laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.

Küche

Waschmaschine

Water front, open bay views from both decks!!

Ocean City MD

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During your stay at this holiday home, you're just a quick walk from Assawoman Bay. Enjoy features like a water park and laundry facilities. The holiday home includes amenities such as free WiFi and a kitchen.

Küche

Waschmaschine

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge MD

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During your stay at this holiday home, you'll be close to Spocott Windmill. Enjoy features like an outdoor pool, laundry facilities and an arcade/games room. The holiday home offers free WiFi and a private pool.

Pool

Küche

* NEWLY RENOVATED** Escape to a Beautiful Getaway on the Chesapeake Bay

Perryville MD

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During your stay at this holiday home, you'll be within walking distance of Chestnut Point Estates and Marina. Features include 1 hot tub and laundry facilities. Free WiFi and a kitchen are available in the holiday home.

Whirlpool

Küche

SUNSET ISLAND Spacious 5-BR - TONS of Amenities

Ocean City MD

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During your stay at this holiday home, you're just a quick walk from Advanced Marina. Enjoy features like an indoor pool, a gym and a water park. The holiday home offers free WiFi and a kitchen.

Pool

Küche

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels MD

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During your stay at this holiday home, you're just a quick walk from Higgins Yacht Yard and Marina. Enjoy features like laundry facilities. The holiday home includes amenities such as free WiFi and a kitchen.

Küche

Waschmaschine

200 steps to the beach!

Rock Hall MD

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During your stay at this holiday home, you're just a quick walk from Chesapeake Bay. Laundry facilities are available. Enjoy your stay with amenities like a kitchen and 1.5 bathrooms in the holiday home.

Küche

Waschmaschine

Summer Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Chesapeake City MD

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During your stay at this holiday home, you'll be within walking distance of Chesapeake City Bridge. You'll find features such as laundry facilities. The holiday home offers in-room jetted baths and a kitchen.

Küche

Waschmaschine

Welcome to Mabel Rose - Delightful 3 bedroom home on the Eastern Shore

Salisbury MD

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During your stay at this holiday home, you're just a quick walk from Coco's Funhouse. Enjoy features like laundry facilities. Enjoy your stay with amenities like a kitchen and 1.5 bathrooms in the holiday home.

Küche

Waschmaschine

True Luxury Vacationing in Downtown Ocean City!

Ocean City MD

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During your stay at True Luxury Vacationing in Downtown Ocean City!, you're just a quick walk from Ocean City Boardwalk. You'll find features such as laundry facilities.

Küche

Waschmaschine

Waterfront Estate w Private Pier, Game Room & Bar

Centreville MD

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During your stay at this holiday home, you'll be close to Earle Landing. You'll find features such as free WiFi in public areas, plus laundry facilities and an arcade/games room. The holiday home includes amenities such as free WiFi and a kitchen.

Küche

Waschmaschine

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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.