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Our top choices for Eastern Shore holiday rentals


Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Guest Suite for up to 2 in a Victorian on the Chester River
Guest Suite for up to 2 in a Victorian on the Chester River
Sailwinds Loft at Cambridge Creek
Sailwinds Loft at Cambridge Creek
Charming Coastal/Country Home w/3 Acres & Sauna!
Charming Coastal/Country Home w/3 Acres & Sauna!
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Top Eastern Shore Hotel Reviews

Crystal Beach Hotel
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Everything you need to know about Eastern Shore holiday rentals
Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Eastern Shore holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Eastern Shore holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Eastern Shore holiday rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Eastern Shore. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .
Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Eastern Shore holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Eastern Shore holiday rentals we have selected for you start as low as £96 per night. Entering your travel dates in the search wizard you might find even better deals!
How to find incredible deals on Eastern Shore rentals
At Expedia, we put the best Eastern Shore holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Eastern Shore rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Eastern Shore holiday.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Eastern Shore. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
Explore a world of travel with Expedia
- 5 Star Hotels in Eastern Shore
- Crowne Plaza Annapolis by IHG
- Hotels with Indoor Pools in Annapolis
- The Inn at Chesapeake Bay Beach Club
- Kent Island Resort
- Annapolis Hotels
- Hotels near Blackwater National Wildlife Refuge
- Comfort Inn & Suites Cambridge
- Days Inn & Suites by Wyndham Cambridge
- Holiday Inn Express Cambridge by IHG
- Hyatt Regency Chesapeake Bay
- Spacious 7
- Cambridge Hotels
- Family Retreat at Lansdowne Manor
- Hgtv quality
- Chesapeake Beach Hotels
- Villas in Chester
- Best Western Denton Inn
- All-Inclusive Hotels in Maryland
- Beach Resorts & in Maryland
- Cheap Hotels in Maryland
- Maryland Hotels
- Downtown Cambridge Hotels
- Gay-Friendly Hotels in Eastern Shore
- Wyndham Hotels in Eastern Shore
- Gay-Friendly Hotels in Easton
- The Oaks Waterfront
- Hilton Garden Inn Kent Island Marina
- Highland Beach Hotels
- Gay-Friendly Hotels in Hunt Meadows
- Pet-Friendly Hotels in Kent Island
- Caravan Parks in Maryland
- Hostels in Maryland
- Lodges in Maryland
- Hotels near Maryland Quiet Waters Park
- North Beach Hotels
- Beach Resorts & in Oxford
- The Oxford Inn
- Ridgely Hotels
- Lowes Wharf Marina Inn
- Minutes from Downtown St. Michael's
- Downtown St. Michaels
- St. Michaels Hotels
- Kent Island Waterfront
- Gay-Friendly Hotels in Tilghman
- Vienna Hotels
- Washington Hotels
- Flights to Annapolis
- Flights to Baltimore
- Flights to California
- Flights to Kent Island
- Flights to St. Michaels
- Flights to Washington
- Flights to Maryland
- Flights from Preston
- Flights from Barclay
- Flights from Queen Anne's County
- Flights from Cambridge
- Flights from Chesapeake Beach
- Flights from Wilkes-Barre (AVP) to Easton (ESN)
- Flights from London (LHR) to Baltimore (BWI)
- Flights from London (LHR) to Easton (ESN)
- Annapolis Holidays
- Blackwater National Wildlife Refuge
- Visit Downtown Cambridge
- Visit Cambridge
- Chesapeake Beach Holidays
- Visit Chesapeake Beach
- Choptank River Lighthouse
- Christ Episcopal Church
- Visit Eastern Shore
- Hammond-Harwood House
- Harriet Tubman Underground Railroad National Historical Park
- Visit Kent Island
- Maryland Holidays
- Visit Maryland
- Visit Oxford
- Visit Shady Side
- Spocott Windmill
- U.s. Naval Academy
- Washington Holidays
- Visit Woolford
















































































