Eastern Shore Holiday Rentals

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Holiday Rentals in Eastern Shore

Aparthotel in Midtown Ocean City

3.0 star property
7.4 out of 10, Good, (1297)
"Scenic area with wonderful wooden bridges and view of water. There was no hot water to shower, but not a deal breaker."
United States
Isolda
The price is AU$147
includes taxes & fees
4 Jan - 5 Jan 2026
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Aparthotel in Downtown Ocean City

2.5 star property
6.2 out of 10, (350)
"Clean and very friendly staff"
United States
Randy
Majestic Hotel & Apartments

Apartment in North Ocean City

3.0 star property
9.2 out of 10, Wonderful, (133)
"Our room was very clean and the ocean view was breathtaking. "
United States
Kelly
Saint Tropez

Cottage in Berlin

3.0 star property
9.4 out of 10, Exceptional, (300)
"Was a great place to bring kids and dogs! "
United States
AMANDA
Shore Point Cottages

Apartment in North Ocean City

3.5 star property
8.6 out of 10, Excellent, (58)
"Property was in a great location. Check in and check out was easy. Having a hot tub and deck with table and chairs was nice. Unit was clean with an exception of the floors. I can understand it being a little sandy because of being at the beach, but there were tortilla chips in several areas of the floor. "
United States
Tami
Club Ocean Villas II by Coolvacay

Condo in Downtown Ocean City

3.5 star property
8.4 out of 10, Very good, (19)
"straight fire, definitely going back"
United States
stephen
The price is AU$701
includes taxes & fees
6 Dec - 7 Dec
Americana Condos 10th street

Holiday Home in North Ocean City

9.8 out of 10, Exceptional, (134)
"Very lovely pkace!! Would def book again!!"
United States
Brenda F.
The price is AU$467
includes taxes & fees
7 Dec - 8 Dec
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

Aparthotel in Downtown Ocean City

3.0 star property
7.4 out of 10, Good, (170)
"Close to boardwalk, beach, shopping and dining. Also it was very affordable."
United States
ANGELA
Boardwalk One

Condo in Downtown Ocean City

10.0 out of 10, Exceptional, (102)
"We had an amazing stay at this property. It was well stocked, clean, had comfy beds, and a beautiful view. "
United States
Abby W.
Updated, Direct Bay Front, Bay Front Pool, 3 Blocks to Beach and Boardwalk

Holiday Home in North Ocean City

9.8 out of 10, Exceptional, (119)
"Great property in a great location. Host was quick to get ahold of and the instructions were incredibly easy. Highly recommend this property for a family or large group. We would stay here again!"
United States
Joseph G.
The price is AU$458
includes taxes & fees
7 Dec - 8 Dec
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

Apartment in Saint Michaels

Downtown St. Michaels | Porch + Pet-Friendly

Condo resort in Midtown Ocean City

3.0 star property
8.4 out of 10, Very good, (39)
"One of the cleanest places I’ve stay at loved it ! "
United States
Kelsey
Bay Club Resort by Coolvacay

Holiday Home in North Ocean City

9.8 out of 10, Exceptional, (11)
"Beautiful home. Our family of 13 were very comfortable and really enjoyed our stay. Only negative was no furniture on the deck. The pictures showed a table and chairs along with couches and comfy chairs. We had to bring out beach chairs to sit. Loved the big side yard and fire pit. "
United States
Peggy K.
⭐️Brand New High End Luxury Bayside Mansion Pool⭐️

Condo in Downtown Ocean City

9.8 out of 10, Exceptional, (62)
"Perfect family beach house, we had a blast! Our family of 7 stayed for 3 nights. We loved the easy check-in, location, and spacious, clean condo. Thank you for letting us use your gorgeous home Kim, we really enjoyed our stay!"
United States
Amy R.
The price is AU$542
includes taxes & fees
8 Dec - 9 Dec
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

Condo in Downtown Ocean City

9.6 out of 10, Exceptional, (49)
"Overall a very nice property. Great location with many food and activity options within walking distance."
United States
Erik G.
SunburstParadise: LUX TH OceanView DOWNTOWN BOARDWALK 3BR 3BA with 2 Car Garage

Condo in Midtown Ocean City

9.8 out of 10, Exceptional, (246)
"Will stay again. Perfect for our needs. "
United States
thomasine m.
The price is AU$347
includes taxes & fees
6 Dec - 7 Dec
Ocean City Maryland Condo, ocean side 50 steps to the beach! On 7 40th Street

Condo in North Ocean City

9.8 out of 10, Exceptional, (70)
"Beautiful property and perfect location! "
United States
Christina T.
Oceanfront 3 Bedroom W Oversized Balcony

Condo in North Ocean City

10.0 out of 10, Exceptional, (317)
"Great location"
United States
Joshua I.
#1 Rated Condo, Oceanfront, with Bay View Too

Holiday Home in Perryville

10.0 out of 10, Exceptional, (20)
"Great waterfront home with sunset views! Plenty of space for our group, very clean, and the hot tub was a perfect bonus. Peaceful, relaxing, and just as described. We’d definitely come back!"
United States
Kaylyn G.
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Apartment in Salisbury

3.0 star property
9.4 out of 10, Exceptional, (23)
"It was a great stay nice comfortable place "
United States
Adam
The price is AU$386
includes taxes & fees
6 Dec - 7 Dec
Salisbury Riverfront Lofts
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$147 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.