Eastern Shore Holiday Rentals

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Our top choices for Eastern Shore holiday rentals

Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Coconut Malorie Resort Ocean City, Ascend Collection Hotel
3.0 star property
Midtown Ocean City
7.4 out of 10, Good, (1,306 reviews)
"The room was dirty "
United States
Kayleigh
The price is NZ$206
includes taxes & fees
8 June - 9 June
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Majestic Hotel & Apartments

Majestic Hotel & Apartments
3.0 star property
Downtown Ocean City
6.2 out of 10, (350 reviews)
"Clean and very friendly staff"
United States
Randy
The price is NZ$228
includes taxes & fees
25 May - 26 May
Majestic Hotel & Apartments

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
8.8 out of 10, Excellent, (3 reviews)
"Very nice cabin. By the town and easy drive to everything. "
United States
Mark
The price is NZ$710
includes taxes & fees
14 May - 15 May
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Boardwalk One

Boardwalk One
3.0 star property
Downtown Ocean City
7.4 out of 10, Good, (171 reviews)
"Close to boardwalk, beach, shopping and dining. Also it was very affordable."
United States
ANGELA
The price is NZ$363
includes taxes & fees
12 May - 13 May
Boardwalk One

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, (251 reviews)
"Great location and clean!"
United States
Susan V.
The price is NZ$466
includes taxes & fees
13 May - 14 May
Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (53 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is NZ$494
includes taxes & fees
10 May - 11 May
BAYSIDE BUNGALOW

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (24 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is NZ$418
includes taxes & fees
10 May - 11 May
Salisbury Riverfront Lofts

The Mallard Apartments

The Mallard Apartments
2.5 star property
Downtown Ocean City
6.0 out of 10, (42 reviews)
"It was a really nice and unique place to stay but windows were broken and didn’t have screens. The tv also did not work."
United States
Kaci
The price is NZ$211
includes taxes & fees
11 May - 12 May
The Mallard Apartments

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, (21 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is NZ$210
includes taxes & fees
11 May - 12 May
Guest Suite for up to 2 in a Victorian on the Chester River

Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!

Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!
North Ocean City
10.0 out of 10, Exceptional, (102 reviews)
"We had a wonderful time and enjoyed the lovely view! It was very clean and beautiful we are looking forward to going back!"
United States
Phonisha W.
The price is NZ$1,282
includes taxes & fees
8 June - 9 June
Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay
3.0 star property
Midtown Ocean City
8.4 out of 10, Very good, (39 reviews)
"One of the cleanest places I’ve stay at loved it ! "
United States
Kelsey
The price is NZ$494
includes taxes & fees
10 May - 11 May
Bay Club Resort by Coolvacay

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
The price is NZ$266
includes taxes & fees
11 May - 12 May
First Floor Studio Apartment in Historic Chestertown

The Escape at the Beach

The Escape at the Beach
North Ocean City
The price is NZ$858
includes taxes & fees
17 May - 18 May
The Escape at the Beach

Safari Apartments

Safari Apartments
3.0 star property
Downtown Ocean City
9.2 out of 10, Wonderful, (35 reviews)
"Great place to stay and very close to the boardwalk. "
United States
Dawn J
The price is NZ$339
includes taxes & fees
10 May - 11 May
Safari Apartments

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (54 reviews)
"Property was exactly as pictured, Crystal is very prompt if contacted & very accomdating to questions. If you are looking in ng for some quiet peacefulness yet close to the water, or nearby towns & attractions & travel with your dog this is the perfect spot! My dogs were very content & I had no worries as to if they would be bothered by distractions because there are no distractions, it was a vacation for them as well as cottage is on a quiet street & it was very nice to sit outside wuth them &...
United States
Shelley
The price is NZ$313
includes taxes & fees
12 May - 13 May
Cottage near the Bay

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, (45 reviews)
"great place, great location, safe secure and everything we needed to get to assateague where the rest of the family were camping"
United States
Thomas B.
The price is NZ$599
includes taxes & fees
11 May - 12 May
Comfortable cottage in gated community, 5 mins to OC and Assateague

Mid Town OceanSide/Block 46th St. Sleeps 5 Location, Location, Location!

Mid Town OceanSide/Block 46th St. Sleeps 5 Location, Location, Location!
Midtown Ocean City
9.0 out of 10, Wonderful, (123 reviews)
"Perfect location. Clean and safe. Thanks for a great stay! "
United States
Kelly G.
The price is NZ$557
includes taxes & fees
11 May - 12 May
Mid Town OceanSide/Block 46th St. Sleeps 5 Location, Location, Location!

Oceanfront and Bay view at the Carousel with indoor pool

Oceanfront and Bay view at the Carousel with indoor pool
North Ocean City
9.8 out of 10, Exceptional, (310 reviews)
"It was a wonderful stay! Beds were comfortable, the kitchen was well stocked, and the views were unbeatable!"
United States
Kim W.
The price is NZ$619
includes taxes & fees
11 May - 12 May
Oceanfront and Bay view at the Carousel with indoor pool

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
10.0 out of 10, Exceptional, (42 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is NZ$351
includes taxes & fees
10 May - 11 May
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

OCHG VIRGINIA LEE

OCHG VIRGINIA LEE
2.0 star property
Downtown Ocean City
7.8 out of 10, Good, (8 reviews)
"We absolutely loved our stay at the OCHG Virginia Lee! We stayed in the top unit and it was amazing! The property manager, Cindy, is top notch and super quick with communication! Highly recommended!"
United States
Chanel
The price is NZ$731
includes taxes & fees
21 May - 22 May
OCHG VIRGINIA LEE
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 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 NZ$133 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.