A marina with numerous boats docked at wooden piers under a clear sky.

Holiday Rentals in Eastern Shore

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Eastern Shore holiday rentals

A row of mobile homes with a one-way sign, a covered porch, and a street sign indicating 'Shore Point Lane'.

1. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (403 reviews)
"Everything was clean and comfortable. Would stay here again."
United States
Kelly
The price is €113
includes taxes & fees
6 Dec - 7 Dec
Shore Point Cottages
A balcony with a view of a river, greenery, and distant buildings.

2. Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
3.0 star property
Midtown Ocean City
7.4 out of 10, Good, (1,331 reviews)
"Our room.seemed to be all new and we loved how there was a separate living room and bedroom with privacy doors. We had a beautiful view of the bay too from the second floor and we loved being on the sunset side of OC:)"
United States
cara
The price is €92
includes taxes & fees
28 Nov - 29 Nov
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
A room with a large bed, multiple windows, and a ceiling fan.

3. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (28 reviews)
"I loved the location, the cleanliness and how good I felt being there. Thank you"
United States
Carmen
The price is €224
includes taxes & fees
8 Nov - 9 Nov
Salisbury Riverfront Lofts
A living room with two grey sofas, a coffee table, and a ceiling fan.

4. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
The price is €287
includes taxes & fees
7 Nov - 8 Nov
Cambridge Apt in Walkable Neighborhood
A deck with a view of a marina, including boats and docks.

5. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is €234
includes taxes & fees
12 Nov - 13 Nov
Cass-N-Reel Luxury Houseboat
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

6. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is €148
includes taxes & fees
3 Dec - 4 Dec
First Floor Studio Apartment in Historic Chestertown
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

7. 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
Millington
9.8 out of 10, Exceptional, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
Guest Suite for up to 2 in a Victorian on the Chester River
A living room with a sofa, a coffee table, a chair, and a dining table. There are two windows with curtains, a lamp, and a painting on the wall.

8. On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.2 out of 10, Wonderful, (44 reviews)
"Great location and very cozy. I wish we could’ve stayed longer."
United States
Christopher W.
The price is €205
includes taxes & fees
8 Nov - 9 Nov
On Main Street - Apartment C - Berlin, MD
A dining area with a wooden table and chairs, a kitchen in the background, and a staircase leading to another level.

9. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is €276
includes taxes & fees
9 Nov - 10 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
A living room with a sofa, a coffee table, and a patterned rug. There is a window with curtains, a door, and a small table with chairs.

10. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"Cute place. Clean, comfortable, and convenient to the soccer complex. I wasn’t familiar with Chesapeake City but we had a great time at the waterfront restaurants."
United States
John P.
The price is €257
includes taxes & fees
8 Nov - 9 Nov
Historic Chesapeake City Stay
A modern kitchen with white cabinets, a central island, and a dining area with a wooden table and chairs.

11. Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!

Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!
Midtown Ocean City
9.8 out of 10, Exceptional, (275 reviews)
"Great place right by the ocean."
United States
Ben P.
Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!
A house with a paved walkway leading to the front door, surrounded by a landscaped garden with mulch and plants.

12. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (52 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is €94
includes taxes & fees
18 Nov - 19 Nov
Country Get Away Studio Apartment
An outdoor dining area with wooden tables and chairs, surrounded by greenery and a large tree.

13. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
The price is €322
includes taxes & fees
17 Nov - 18 Nov
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A waterfront property with multiple balconies, a dock with boats, and a clear blue sky.

14. Canal front with boat slip, boat ramp, WiFi, and roku streaming TV

Canal front with boat slip, boat ramp, WiFi, and roku streaming TV
Midtown Ocean City
9.8 out of 10, Exceptional, (10 reviews)
"Really cute place in a great location!"
United States
Mindie F.
The price is €139
includes taxes & fees
9 Nov - 10 Nov
Canal front with boat slip, boat ramp, WiFi, and roku streaming TV
A house with a blue front door, two windows, and a small porch.

15. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is €259
includes taxes & fees
6 Nov - 7 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

16. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
Sailwinds Loft at Cambridge Creek
A room with teal walls, a gray sofa, a white dresser, and a ceiling fan.

17. Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N

Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
North Ocean City
9.2 out of 10, Wonderful, (54 reviews)
"Very friendly!"
United States
Anonymous traveller
The price is €177
includes taxes & fees
9 Nov - 10 Nov
Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
A two-story house with a porch, two windows, and a door.

18. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
Denton
10.0 out of 10, Exceptional, (15 reviews)
"The house was perfect, welcoming and comfortable, will be coming back again"
United States
Dallas S.
Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
A beachside table with a decorative centerpiece, two lanterns, and a view of the ocean.

19. BeachBox® III • Unreal Views • Oceanfront Balcony • Worcester House 401

BeachBox® III • Unreal Views • Oceanfront Balcony • Worcester House 401
Midtown Ocean City
10.0 out of 10, Exceptional, (30 reviews)
"A true gem! Perfect location, excellent accommodations, and quick, friendly communication from the host. We had a wonderful stay and would happily return."
United States
Bethzaida
The price is €213
includes taxes & fees
9 Nov - 10 Nov
BeachBox® III • Unreal Views • Oceanfront Balcony • Worcester House 401
A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

20. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is €319
includes taxes & fees
23 Nov - 24 Nov
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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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Top Eastern Shore Hotel Reviews

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

8/10 Good
"I liked a lot of this stay, but the one thing that really bothered me was that my room had a door to the next room, which would allow folks with large groups be connected. But, those doors have no insulation so they are useless in blocking sound between the rooms. Three night, I had 3 different people in that room and I heard everything. They were not yelling or fighting or anything, just normal everyday conversations. It was the third one that really bothered me because they were night owls, and would carry on a conversation or play music and I heard it all. I am a solo traveling so I am not talking to anyone unless I am on the phone. I could get to sleep until 3 am and I had a 280 mile drive that day."
james 2-night trip
Posted 1 hour ago
Grand Hotel Ocean City Oceanfront

Find out more about Eastern Shore

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 €92 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. 

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