Eastern Shore Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Eastern Shore holiday rentals

View from room

Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (303 reviews)
"The location of shore point cottages is a pleasant and peaceful one. It's far enough out of the hustle and bustle of the boardwalk area. Yet close enough to everything that makes Ocean City a fun place to visit. Definitely a place to come back to and stay again."
United States
Mike
Shore Point Cottages
Exterior

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, (1,300 reviews)
"Everything was great :) Great location...great staff!"
United States
Daria
The price is HK$598
HK$763 total
includes taxes & fees
15 Mar - 16 Mar
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
Outdoor pool

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, (43 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 HK$782
HK$2,495 total
includes taxes & fees
15 Feb - 16 Feb
Comfortable cottage in gated community, 5 mins to OC and Assateague
Exterior

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"The accommodation description is good; the actual accommodations are great, better than expected, truly a quiet country getaway with many unexpected extras. Deciding to stay here was great decision. It's done right."
United States
John L.
The price is HK$547
HK$870 total
includes taxes & fees
19 Feb - 20 Feb
Country Get Away 1 Bedroom Apartment
2 bedrooms, individually decorated, individually furnished

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (23 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is HK$544
HK$1,974 total
includes taxes & fees
23 Feb - 24 Feb
Salisbury Riverfront Lofts
Exterior

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
9.6 out of 10, Exceptional, (19 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
Guest Suite for up to 2 in a Victorian on the Chester River
Beach nearby

On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.2 out of 10, Wonderful, (29 reviews)
"We loved everything about our stay! This place is adorable and the location is awesome!"
United States
kelly K.
The price is HK$563
HK$1,812 total
includes taxes & fees
15 Feb - 16 Feb
On Main Street - Apartment C - Berlin, MD
Fridge, microwave, oven, stovetop

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (11 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is HK$1,097
HK$1,727 total
includes taxes & fees
17 Feb - 18 Feb
Quarry Landing - Center of Town & River View - 3 Bedroom
Smart TV

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
9.8 out of 10, Exceptional, (8 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is HK$938
HK$1,259 total
includes taxes & fees
16 Feb - 17 Feb
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Front of property

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is HK$719
HK$2,010 total
includes taxes & fees
21 Feb - 22 Feb
6 Mi to Salisbury: Forest-view Sanctuary!
Fridge, microwave, oven, stovetop

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (58 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is HK$1,090
HK$2,034 total
includes taxes & fees
14 Feb - 15 Feb
Deal Island Bay Cottage
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is HK$774
HK$1,241 total
includes taxes & fees
16 Feb - 17 Feb
First Floor Studio Apartment in Historic Chestertown
Beach

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, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is HK$921
HK$2,233 total
includes taxes & fees
14 Feb - 15 Feb
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"Yes she was welcoming "
United States
Garry B.
The price is HK$844
HK$2,179 total
includes taxes & fees
15 Feb - 16 Feb
Historic Chesapeake City Stay
Exterior

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, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is HK$549
HK$1,949 total
includes taxes & fees
17 Feb - 18 Feb
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Interior

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (29 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is HK$1,094
HK$1,947 total
includes taxes & fees
11 Mar - 12 Mar
Private 3 room Queen Suite w/Kitchenette
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very clean, and very comfortable beds."
United States
Edward R.
The price is HK$1,133
HK$2,767 total
includes taxes & fees
16 Feb - 17 Feb
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (12 reviews)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
The price is HK$1,133
HK$2,767 total
includes taxes & fees
16 Feb - 17 Feb
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Fridge, microwave, oven, stovetop

Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (19 reviews)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
United States
Ryan B.
The price is HK$1,048
HK$2,093 total
includes taxes & fees
22 Feb - 23 Feb
Cozy Barn Loft: Country Views & Central to Beaches
Exterior

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, (35 reviews)
"Very cool place. "
United States
Eric L.
The price is HK$1,372
HK$1,628 total
includes taxes & fees
16 Feb - 17 Feb
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Eastern Shore Hotel Reviews

Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites

10/10 Excellent
"Spacious room, great amenities, and rain shower!"
Kristin 2-night trip
Posted 4 days ago
Hilton Ocean City Oceanfront Suites

Find out more about Eastern Shore

Search for holiday rentals in Eastern Shore on Expedia! You can easily find your home rentals, villas, holiday apartments in Eastern Shore using one of the methods below:

  • View our selection of featured holiday rentals in Eastern Shore
  • Use the map to find apartments and other holiday homes in the Eastern Shore neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Eastern Shore while they last

Look no further and take a look at our great range of rental properties in Eastern Shore!