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

Eastern Shore Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Eastern Shore holiday rentals

A gym with treadmills, dumbbells, and exercise balls, large windows with a view of the ocean.

1. 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, (1,330 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 AU$168
includes taxes & fees
30 Oct - 31 Oct
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
A room with a large bed, multiple windows, and a ceiling fan.

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$362
includes taxes & fees
28 Oct - 29 Oct
Salisbury Riverfront Lofts
A living room with two grey sofas, a coffee table, and a ceiling fan.

3. 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 AU$465
includes taxes & fees
20 Oct - 21 Oct
Cambridge Apt in Walkable Neighborhood
A covered patio with a table and chairs, overlooking a beach.

4. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (531 reviews)
"Right in front of the board walk and almost center to everything"
United States
Wilber
The price is AU$110
includes taxes & fees
20 Oct - 21 Oct
Majestic Hotel & Apartments
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is AU$232
includes taxes & fees
26 Oct - 27 Oct
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.

6. 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)
"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$183
includes taxes & fees
20 Oct - 21 Oct
Guest Suite for up to 2 in a Victorian on the Chester River
A riverside dock with boats, a covered seating area, and a bridge in the background.

7. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (30 reviews)
"This is a great place, to feel comfortable. Exactly as advertised Just around the corner from Schaeffers."
United States
Janice H.
The price is AU$397
includes taxes & fees
21 Oct - 22 Oct
Historic Chesapeake City Stay
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

8. 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, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is AU$377
includes taxes & fees
20 Oct - 21 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A covered patio with a table and chairs, a sliding glass door, and a white fence.

9. Monte Carlo Condos

Monte Carlo Condos
3.0 star property
Downtown Ocean City
7.0 out of 10, Good, (74 reviews)
"Unexpected pet fee on top of resort fees we did expect. Nice and close to boardwalk. Room was quiet, private, spacious."
United States
Ben
The price is AU$311
includes taxes & fees
26 Oct - 27 Oct
Monte Carlo Condos
A lighthouse with a white exterior, a balcony, and a metal roof.

10. 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 stay"
United States
Michael V.
The price is AU$519
includes taxes & fees
2 Nov - 3 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

11. 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 AU$362
includes taxes & fees
20 Oct - 21 Oct
Sailwinds Loft at Cambridge Creek
A beachside boardwalk with shops, a Ferris wheel, and a tram.

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

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (43 reviews)
"Had great mini vac . The vrbo was right down town lots great shops and good choices for meals. All ready thinking about going back"
United States
Jeffry C.
The price is AU$358
includes taxes & fees
15 Nov - 16 Nov
On Main Street - Apartment C - Berlin, MD
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

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 AU$561
includes taxes & fees
18 Nov - 19 Nov
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A waterfront property with multiple-story buildings, a dock with boats, and a wooden pier.

14. BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
North Ocean City
9.8 out of 10, Exceptional, (163 reviews)
"Great house, location was excellent "
United States
Mike G.
The price is AU$441
includes taxes & fees
1 Nov - 2 Nov
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
A modern kitchen with white cabinets, a central island, and a dining area with a wooden table and chairs.

15. 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 spot, clean and affordable!"
United States
Beth H.
The price is AU$298
includes taxes & fees
3 Nov - 4 Nov
Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!
A room with teal walls, a gray sofa, a white dresser, and a ceiling fan.

16. 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)
"Pretty decent, good location, decently clean though the bathroom was a bit ehh and the whole room could use a couple more amenities. Overall good, affordable option compared to similar rooms and places in the area."
United States
Siddhartha B.
The price is AU$301
includes taxes & fees
20 Oct - 21 Oct
Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
A dining area with a wooden table and chairs, a ceiling fan, and large windows with blinds.

17. Beach Paradise 105 - Beach Home at Broad Marsh OC

Beach Paradise 105 - Beach Home at Broad Marsh OC
North Ocean City
9.8 out of 10, Exceptional, (14 reviews)
"Loved this property. It was clean and had everything we needed. Had a wonderful stay!! Highly recommend!"
United States
renee d.
The price is AU$432
includes taxes & fees
1 Nov - 2 Nov
Beach Paradise 105 - Beach Home at Broad Marsh OC
A large outdoor swimming pool with people swimming and lounging, surrounded by a fence and shaded areas.

18. Comfortable cottage in gated community, 5 mins to OC and Assateague

Comfortable cottage in gated community, 5 mins to OC and Assateague
Assateague Pointe
9.8 out of 10, Exceptional, (58 reviews)
"The cottage location is great for golf, less than 20 minutes ride to most courses. Also dining in Berlin is better than traffic to Oean City."
United States
Joe
The price is AU$509
includes taxes & fees
21 Oct - 22 Oct
Comfortable cottage in gated community, 5 mins to OC and Assateague
A balcony with a view of a parking lot and buildings.

19. Americana Condos 10th street

Americana Condos 10th street
3.5 star property
Downtown Ocean City
8.6 out of 10, Excellent, (34 reviews)
"Wonderful views and so big!"
United States
Liz
The price is AU$638
includes taxes & fees
27 Oct - 28 Oct
Americana Condos 10th street
An open door leading to a bedroom with a bed, a nightstand, and a lamp.

20. 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, (25 reviews)
"Great location with plenty of space to relax."
United States
Doug R.
The price is AU$269
includes taxes & fees
8 Nov - 9 Nov
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
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

Quality Inn Oceanfront

Quality Inn Oceanfront

8/10 Good
"We stayed in a first floor beachfront room during the offseason. Definitely a great beach hotel which I can see myself staying at in the summer, but not somewhere I'd stay again otherwise (if that makes sense?). Like, the door opened right up to the beach entrance which was amazing but only if you're there for the beach. Otherwise, it's dated, kinda dingy, and just "mid." Oh, and be warned, there birds in the atrium. And not birds that found their way in from outside. They are the largest parrots I have ever seen and they are LOUD. Our door was right next to their cages. It was kinda shocking because I didn't notice when I first entered the room. After a few minutes of settling in, we hear "BACAWWWW!!" a couple of times. We opened the door to investigate and, lo and behold, giant Amazonian parrots! lol. Crazy. I don't remember seeing that mentioned in any of the reviews I read. The staff covers their cages for the night and they did not disrupt our sleep. Definitely worth mentioning though! Overall, it was okay. Easy check in and out. Ample parking. Friendly staff. Go in the summer"
Benjamin 1-night trip
Posted less than an hour ago
Quality Inn 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, 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$150 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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