Eastern Shore Holiday Rentals

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Our top choices for Eastern Shore holiday rentals

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 AU$153
includes taxes & fees
8 June - 9 June
Majestic Hotel & Apartments

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, (1,308 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 AU$190
includes taxes & fees
10 June - 11 June
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

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 AU$388
includes taxes & fees
8 June - 9 June
Salisbury Riverfront Lofts

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (21 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is AU$392
includes taxes & fees
10 June - 11 June
Historic Chesapeake City Stay

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (55 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 AU$264
includes taxes & fees
16 June - 17 June
Cottage near the Bay

On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (33 reviews)
"We loved everything about our stay! This place is adorable and the location is awesome!"
United States
kelly K.
The price is AU$398
includes taxes & fees
7 June - 8 June
On Main Street - Apartment C - Berlin, MD

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 AU$497
includes taxes & fees
16 June - 17 June
ELIS APARTMENT

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (112 reviews)
"Every thing was great"
United States
lesia k.
The price is AU$225
includes taxes & fees
17 June - 18 June
First Floor Studio Apartment in Historic Chestertown

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, (24 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$178
includes taxes & fees
9 June - 10 June
Guest Suite for up to 2 in a Victorian on the Chester River

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (43 reviews)
"Wonderful place and host, very peaceful and quiet with plenty of nature !!!"
United States
Daniel V.
The price is AU$159
includes taxes & fees
16 June - 17 June
Country Get Away Studio Apartment

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (30 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is AU$359
includes taxes & fees
9 June - 10 June
Sailwinds Loft at Cambridge Creek

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, (21 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is AU$411
includes taxes & fees
23 June - 24 June
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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, (19 reviews)
"Property was nice and clean"
United States
Luke S.
The price is AU$297
includes taxes & fees
8 June - 9 June
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is AU$379
includes taxes & fees
25 June - 26 June
6 Mi to Salisbury: Forest-view Sanctuary!

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 AU$398
includes taxes & fees
8 June - 9 June
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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, (10 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is AU$229
includes taxes & fees
9 June - 10 June
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

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, (47 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 AU$661
includes taxes & fees
16 June - 17 June
Comfortable cottage in gated community, 5 mins to OC and Assateague

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 AU$533
includes taxes & fees
7 June - 8 June
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (55 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AU$389
includes taxes & fees
22 June - 23 June
BAYSIDE BUNGALOW

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is AU$398
includes taxes & fees
9 June - 10 June
Charming Coastal/Country Home w/3 Acres & Sauna!
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$190 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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