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, (369 reviews)
"Good and cute environment"
United States
junghyun
Shore Point Cottages

2. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (27 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
The price is AU$347
includes taxes & fees
5 Oct - 6 Oct
Salisbury Riverfront Lofts

3. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (496 reviews)
"Great location--Very close to the steps and boardwalk!"
United States
ALEXIS
The price is AU$118
includes taxes & fees
5 Oct - 6 Oct
Majestic Hotel & Apartments

4. 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, (1,318 reviews)
"The hotel did not disappoint. The room, the tub and especially the shower was the best. We also loved the view. Would come back again and get the same room. We had the presidential suite."
United States
Nichole
The price is AU$172
includes taxes & fees
7 Sept - 8 Sept
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

5. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is AU$391
includes taxes & fees
7 Sept - 8 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

6. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is AU$223
includes taxes & fees
7 Sept - 8 Sept
First Floor Studio Apartment in Historic Chestertown

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is AU$410
includes taxes & fees
7 Sept - 8 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!

8. Safari Apartments

Safari Apartments
3.0 star property
Downtown Ocean City
9.4 out of 10, Exceptional, (44 reviews)
"Friendly staff. Easy check in/out. Clean place. Great area close to the boardwalk. Will definitely rent again."
United States
David
The price is AU$288
includes taxes & fees
20 Sept - 21 Sept
Safari Apartments

9. 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, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is AU$408
includes taxes & fees
14 Sept - 15 Sept
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10. 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, (27 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is AU$177
includes taxes & fees
15 Sept - 16 Sept
Guest Suite for up to 2 in a Victorian on the Chester River

11. 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, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is AU$599
includes taxes & fees
5 Oct - 6 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

12. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is AU$358
includes taxes & fees
5 Oct - 6 Oct
Sailwinds Loft at Cambridge Creek

13. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (29 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
The price is AU$388
includes taxes & fees
8 Sept - 9 Sept
Historic Chesapeake City Stay

14. Boardwalk Terrace Apartments

Boardwalk Terrace Apartments
3.0 star property
Downtown Ocean City
5.8 out of 10, (111 reviews)
"Staff was very professional and polite. Ocean veiw was amazing from the balcony. Room was clean and comfortable. Location was perfect for beach and shops and restaurants."
United States
Melissa
The price is AU$113
includes taxes & fees
5 Oct - 6 Oct
Boardwalk Terrace Apartments

15. ELIS APARTMENT

ELIS APARTMENT
3.0 star property
Downtown Ocean City
9.4 out of 10, Exceptional, (6 reviews)
"It was clean and comfortable very cool and quiet didn't have to use AC"
United States
Norda
The price is AU$351
includes taxes & fees
13 Sept - 14 Sept
ELIS APARTMENT

16. Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Salisbury
9.8 out of 10, Exceptional, (24 reviews)
"First time using VRBO and it was more than inexpected"
United States
Robert J.
The price is AU$254
includes taxes & fees
5 Oct - 6 Oct
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

17. On Main Street - Apartment B - Berlin, MD

On Main Street - Apartment B - Berlin, MD
Downtown Berlin
8.8 out of 10, Excellent, (47 reviews)
"I actually had an emergency at home and only stayed the first night. My husband was there the entire time and found it perfect for his needs!"
United States
Mary L.
The price is AU$394
includes taxes & fees
6 Sept - 7 Sept
On Main Street - Apartment B - Berlin, MD

18. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (64 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is AU$431
includes taxes & fees
6 Sept - 7 Sept
BAYSIDE BUNGALOW

19. The Mallard Apartments

The Mallard Apartments
2.5 star property
Downtown Ocean City
5.8 out of 10, (57 reviews)
"Not what is lists for, place was very dirty, sheets, sofa, carpets, beds, bathroom. Place smelled like must, humidity and mold. . Do not recommend anyone staying here"
United States
Diego
The price is AU$160
includes taxes & fees
7 Sept - 8 Sept
The Mallard Apartments

20. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (48 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is AU$157
includes taxes & fees
15 Sept - 16 Sept
Country Get Away Studio Apartment
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

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, 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 favourite 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 depend 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 AU$113 per night. Entering your travel dates in the search wizard might find you 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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