Holiday Rentals in Eastern Shore

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Our top choices for Eastern Shore holiday rentals

Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
6.0 out of 10, (368 reviews)
"Amazing location and staff was very nice! It felt super safe. As a female solo traveler, felt super safe here!"
United States
Mia
The price is €79
includes taxes & fees
23 Jun - 24 Jun
Majestic Hotel & Apartments

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (22 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is €248
includes taxes & fees
23 Jun - 24 Jun
Historic Chesapeake City Stay

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, (23 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is €252
includes taxes & fees
23 Jun - 24 Jun
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (42 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is €101
includes taxes & fees
2 Jul - 3 Jul
Country Get Away Studio Apartment

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (56 reviews)
"Cottage was exactly as listed. Great value"
United States
Tom B.
The price is €167
includes taxes & fees
24 Jun - 25 Jun
Cottage near the Bay

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (113 reviews)
"Every thing was great"
United States
lesia k.
The price is €142
includes taxes & fees
23 Jun - 24 Jun
First Floor Studio Apartment in Historic Chestertown

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
10.0 out of 10, Exceptional, (3 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is €298
includes taxes & fees
23 Jun - 24 Jun
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

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
9.6 out of 10, Exceptional, (20 reviews)
"Property was nice and clean"
United States
Luke S.
The price is €215
includes taxes & fees
30 Jun - 1 Jul
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.2 out of 10, Wonderful, (25 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is €258
includes taxes & fees
30 Jun - 1 Jul
Salisbury Riverfront Lofts

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, (23 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 €113
includes taxes & fees
29 Jun - 30 Jun
Guest Suite for up to 2 in a Victorian on the Chester River

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, (46 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is €292
includes taxes & fees
29 Jun - 30 Jun
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is €236
includes taxes & fees
30 Jun - 1 Jul
6 Mi to Salisbury: Forest-view Sanctuary!

On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (35 reviews)
"We loved everything about our stay! This place is adorable and the location is awesome!"
United States
kelly K.
The price is €275
includes taxes & fees
5 Jul - 6 Jul
On Main Street - Apartment C - Berlin, MD

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Berlin
9.8 out of 10, Exceptional, (104 reviews)
"This property and its owner were everything we look for in a vacation rental. Listing is as an old farm house does not do it justice. The owner has carefully curated it it with an electric collection of furniture ,pottery and various hand crafted items. She has put her heart and soul into this house and you can feel.it ad soon as you step inside. We will definitely be back.😍😍😍😍😍 The McCartney's and the Horneffs.......Thanks again for everything Laurie."
United States
Melinda
The price is €305
includes taxes & fees
23 Jun - 24 Jun
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

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
10.0 out of 10, Exceptional, (11 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is €144
includes taxes & fees
23 Jun - 24 Jun
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

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, (1,308 reviews)
"The room had issues in the toilet and also the ceiling broke and ended up ruining a pair of shoes from a leakage. The description of the pictures was not accurate to the room. I was supposed to have a suite and had one regular room with balcony."
United States
Eivy
The price is €175
includes taxes & fees
1 Jul - 2 Jul
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

ELIS APARTMENT

ELIS APARTMENT
3.0 star property
Downtown Ocean City
9.2 out of 10, Wonderful, (5 reviews)
"Very nice place "
United States
Marvin R
The price is €248
includes taxes & fees
28 Jun - 29 Jun
ELIS APARTMENT

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
9.8 out of 10, Exceptional, (45 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is €187
includes taxes & fees
25 Jun - 26 Jun
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
7.8 out of 10, Good, (7 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is €342
includes taxes & fees
20 Jul - 21 Jul
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (32 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is €220
includes taxes & fees
25 Jun - 26 Jun
Sailwinds Loft at Cambridge Creek
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, apart-hotels, 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 €175 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. 

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