Eastern Shore Vacation Rentals

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Showing 1 - 10 of 23 Eastern Shore homes with 4 to 5 bedrooms.

Our larger family Eastern Shore vacation homes are ideal for multi-generational or two families to split for your summer vacation. With amenities such as private pools, docks, hot tubs or game rooms, it could be all you need for summer fun!

  Name | Bedrooms | Sleeps | Rate << Prev Go to page: 1 2 3 Next >>  

Bridge House

21764 Camper Circle
Tilghman Island - House
Bedrooms 4
Sleeps: 8
Pets Allowed, Dock Suitable For Boating, Linens/Towels Provided


Bridge House offers a full season experience to guests who enjoy not only waterviews but the activity of a working waterway. The watermen's boat...more
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Red Shake Cottage

109 South Street
Oxford - Cottage
Bedrooms 4
Sleeps: 8
Pets Allowed, Linens/Towels Provided


We love this cottage for many reasons - the great location - you can walk to everything, particularly our favorite ice cream store - Victors,...more
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Hampden

3536 Hampden Drive
Trappe - House
Bedrooms 5
Sleeps: 10
Pets Allowed, Private Pool, Dock Suitable For Boating, Linens/Towels Provided


Hampden is the oldest brick structure in Talbot County. Step back in time, circa 1663, and wrap yourself around the charm and ambience of...more
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The Cove

8790 Kemp Road
Easton - House
Bedrooms 4
Sleeps: 8
No Pets, Private Pool, Kayak Included, Dock Suitable For Boating, Linens/Towels Provided


A traditional style home with great outdoor porches, this home is like a step back a few generations to a gracious old home where taking...more
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River House on Moon Bay

25404 Learman Road
Chestertown - House
Bedrooms 4
Sleeps: 8
No Pets, Linens/Towels Provided


The ever-changing Chester River is the focal point of the house. Watermen called this section of the river “Moon Bay,” hence the name The River...more
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Bushey Heath Farm

25608 Bushey Heath Road
Royal Oak - House
Bedrooms 4
Sleeps: 8
Pets Allowed, Private Pool


A traditional Eastern Shore farmhouse, Bushey Heath Farm is a rustic retreat just miles from St. Michaels. Tucked away on a very private 90...more
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Sunset Bay

5378 Casson Neck Road
Cambridge - House
Bedrooms 5
Sleeps: 16
Pets Allowed, Private Pool, Kayak Included, Linens/Towels Provided


Wide water views with great sunsets, Sunset Bay is perfect for those larger family vacations where you need the extra space and activities. Private...more
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Blue Gates

28210 Old Country Club Road
Easton - House
Bedrooms 5
Sleeps: 10
No Pets, Private Pool, Dock Suitable For Boating, Linens/Towels Provided


Elegantly furnished and located in a prestigious estate area of Talbot County, Blue Gates offers a chance to experience the best in Eastern Shore Living....more
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East Bonfield Farm

4630 Boone Creek Road
Oxford - House
Bedrooms 5
Sleeps: 10
Pets Allowed, Private Pool, Linens/Towels Provided


Just on the outskirts of Oxford, Bonfield Farm is an expansive telescope home with wraparound views of Boone Creek. This home gives you the...more
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Chesapeake Pines

6760 Thorneton Road
Royal Oak - House
Bedrooms 4
Sleeps: 8
No Pets, Dock Suitable For Boating, Linens/Towels Provided


A taste of paradise on the Chesapeake—the beauty hits you before you enter the front door! Spacious, comfortable, convenient home, includes all amenities...more
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21 S. Harrison Street
Easton, MD 21601


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