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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Eastern Shore villas

A balcony with a view of the beach and ocean.

1. Beach Front Villa in Dewey Beach

Beach Front Villa in Dewey Beach
4.0 star property
Rehoboth by the Sea
The price is Rp36.485.513
Rp51.083.336 total
includes taxes & fees
9 Nov - 10 Nov
Beach Front Villa in Dewey Beach
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.
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Learn more about Eastern Shore

Charming coastal towns and pristine beaches dot the Chesapeake Bay's eastern shoreline, inviting you to explore maritime history and savour fresh seafood. Kayak through serene marshlands, visit Assateague Island's wild ponies, or take a scenic drive to discover quaint antique shops and waterfront restaurants.

See all hotels in Eastern Shore
A historic white mansion with a sign in front.

Top reviews in Eastern Shore

A two-story house with a porch, a front door, and a small garden area.
The Wildset

The Wildset

The Wildset
Downtown St. Michaels

8/10 Good

Expensive and basic
United Kingdom
Dina
Reviewed May 14, 2026
The Wildset

Frequently Asked Questions

How much do villas in Eastern Shore cost?

Rates for villas in Eastern Shore range between Rp36.485.513 and Rp36.485.513 per night. No matter your budget, you can find someplace that fits your needs on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many villas are there in Eastern Shore?

Choose from villas in Eastern Shore. Whether you're getting away with your family or a bunch of friends, and wherever your destination, Expedia will help you secure the perfect place.

Why book your villa in Eastern Shore with Expedia?

We think organising a holiday shouldn't be hard, so if you're in search of villas at a great price, Expedia has you covered. Keep costs down and select an all-inclusive stay, or splurge on a 5-star villa to treat your sweetheart. Our handy filters make it simple to find a place in Eastern Shore that checks your boxes.

How can I find cheap villas in Eastern Shore?

Expedia is here to help you look for cheap villas in Eastern Shore. Use the filter tool to choose star rating, amenities and budget to refine your search and find the best place to stay in a few quick keystrokes.

What is there to do near my villa in Eastern Shore?

The best accessory to pack for your Eastern Shore trip is a well-thought-out itinerary! Jolly Roger at the Pier, Inlet Park and Ember's Island Miniature Golf are among the biggest sights if you're staying in Ocean City. Salisbury also has plenty of famous attractions, such as Poplar Hill Mansion. Looking for more? Drop by Pemberton Historical Park and Ward Museum of Wildfowl Art too.