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

Eastern Shore Holiday Rentals

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Our top choices for Eastern Shore holiday rentals

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 NZ$214
includes taxes & fees
1 Dec - 2 Dec
Shore Point Cottages

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 NZ$184
includes taxes & fees
28 Nov - 29 Nov
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

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 NZ$455
includes taxes & fees
8 Nov - 9 Nov
Salisbury Riverfront Lofts

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 NZ$574
includes taxes & fees
15 Nov - 16 Nov
Cambridge Apt in Walkable Neighborhood

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 NZ$459
includes taxes & fees
12 Nov - 13 Nov
Cass-N-Reel Luxury Houseboat

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 NZ$267
includes taxes & fees
10 Nov - 11 Nov
First Floor Studio Apartment in Historic Chestertown

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
The price is NZ$207
includes taxes & fees
11 Nov - 12 Nov
Guest Suite for up to 2 in a Victorian on the Chester River

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 NZ$396
includes taxes & fees
8 Nov - 9 Nov
On Main Street - Apartment C - Berlin, MD

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 NZ$527
includes taxes & fees
9 Nov - 10 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!

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 NZ$522
includes taxes & fees
15 Nov - 16 Nov
Historic Chesapeake City Stay

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.
The price is NZ$358
includes taxes & fees
11 Nov - 12 Nov
Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!

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 NZ$184
includes taxes & fees
16 Nov - 17 Nov
Country Get Away Studio Apartment

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 NZ$678
includes taxes & fees
30 Nov - 1 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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 NZ$273
includes taxes & fees
9 Nov - 10 Nov
Canal front with boat slip, boat ramp, WiFi, and roku streaming TV

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 NZ$509
includes taxes & fees
9 Nov - 10 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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.
The price is NZ$422
includes taxes & fees
19 Nov - 20 Nov
Sailwinds Loft at Cambridge Creek

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 NZ$349
includes taxes & fees
11 Nov - 12 Nov
Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N

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.
The price is NZ$623
includes taxes & fees
1 Dec - 2 Dec
Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

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 NZ$400
includes taxes & fees
9 Nov - 10 Nov
BeachBox® III • Unreal Views • Oceanfront Balcony • Worcester House 401

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 NZ$596
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

Find out more about Eastern Shore

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Eastern Shore holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Eastern Shore. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Eastern Shore. Seeing all the best attractions is bound to make you fall in love with Eastern Shore. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Eastern Shore short-term rentals, that won’t be hard to do.

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