Eastern Shore Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Eastern Shore

Salisbury Riverfront Lofts
3.0 star property
9.2 out of 10, Wonderful, (22)
"Very nice place clean & roomy."
Brian
The price is AU$388
includes taxes & fees
19 Oct - 20 Oct
Salisbury Riverfront Lofts
Comfortable cottage in gated community, 5 mins to OC and Assateague
9.8 out of 10, Exceptional, (41)
"Thank you for the use of your lovely house. Enjoyed our stay. "
Michael H.
The price is AU$493
includes taxes & fees
4 Nov - 5 Nov
Comfortable cottage in gated community, 5 mins to OC and Assateague
Country Get Away 1 Bedroom Apartment
9.8 out of 10, Exceptional, (39)
"Perfect in every way… a great stay"
Robert B.
The price is AU$174
includes taxes & fees
11 Nov - 12 Nov
Country Get Away 1 Bedroom Apartment
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
2.0 star property
9.8 out of 10, Exceptional, (6)
"Great stay. Everything you need, quiet and clean. "
Melissa J.
The price is AU$250
includes taxes & fees
19 Oct - 20 Oct
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
The price is AU$367
includes taxes & fees
22 Oct - 23 Oct
6 Mi to Salisbury: Forest-view Sanctuary!
Boardwalk One
3.0 star property
7.4 out of 10, Good, (170)
"Close to boardwalk, beach, shopping and dining. Also it was very affordable."
ANGELA
Boardwalk One
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
3.0 star property
7.4 out of 10, Good, (1292)
"We had a really lovely time and the staff was incredibly helpful with all our needs to the music festival we were in town for."
Dana
The price is AU$169
includes taxes & fees
27 Oct - 28 Oct
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
10.0 out of 10, Exceptional, (27)
"Very nice cottage, as advertised"
nick k.
The price is AU$323
includes taxes & fees
21 Oct - 22 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
On Main Street - Apartment C - Berlin, MD
9.4 out of 10, Exceptional, (27)
"Very quaint. Well appointed unit with a nice in town location. Parking was no problem. Would book again."
Clark
The price is AU$348
includes taxes & fees
21 Oct - 22 Oct
On Main Street - Apartment C - Berlin, MD
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (16)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
Tracy S.
The price is AU$454
includes taxes & fees
22 Oct - 23 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Private 3 room Queen Suite w/Kitchenette
10.0 out of 10, Exceptional, (29)
"Perfect location for that town. "
Hisham M.
The price is AU$403
includes taxes & fees
27 Oct - 28 Oct
Private 3 room Queen Suite w/Kitchenette
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
2.0 star property
9.8 out of 10, Exceptional, (9)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
Lauren V.
The price is AU$548
includes taxes & fees
20 Oct - 21 Oct
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
9.6 out of 10, Exceptional, (16)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
Aaron N.
The price is AU$548
includes taxes & fees
20 Oct - 21 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Clean, modern and well-equipped Ocean City condo
10.0 out of 10, Exceptional, (15)
"Clean, comfortable, convenient, and just as advertised. Host was communicative and made the stay enjoyable. Would definitely stay here again. "
Sara H.
Clean, modern and well-equipped Ocean City condo
Guest Suite for up to 2 in a Victorian on the Chester River
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
Cynthia C.
The price is AU$195
includes taxes & fees
28 Oct - 29 Oct
Guest Suite for up to 2 in a Victorian on the Chester River
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
9.6 out of 10, Exceptional, (14)
"Property was nice and clean"
Luke S.
The price is AU$291
includes taxes & fees
19 Oct - 20 Oct
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
Michael S.
The price is AU$426
includes taxes & fees
28 Oct - 29 Oct
Historic Chesapeake City Stay
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (103)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
Mary
The price is AU$247
includes taxes & fees
23 Oct - 24 Oct
First Floor Studio Apartment in Historic Chestertown
Deal Island Bay Cottage
9.6 out of 10, Exceptional, (57)
"We got every year and stay here, it’s great! "
Margaret H.
The price is AU$408
includes taxes & fees
19 Oct - 20 Oct
Deal Island Bay Cottage
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
Stephanie S.
The price is AU$394
includes taxes & fees
19 Oct - 20 Oct
Relax on Kent Island in 3 Bedroom Home w/Waterview
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.
Save an average of 15% on thousands of hotels when you're signed in

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$169 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.