Eastern Shore Holiday Rentals

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Our top choices for Eastern Shore holiday rentals

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, (1,305 reviews)
"Everything was great :) Great location...great staff!"
United States
Daria
The price is AU$164
includes taxes & fees
28 Apr - 29 Apr
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

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 AU$348
includes taxes & fees
6 May - 7 May
Salisbury Riverfront Lofts

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is AU$377
includes taxes & fees
10 May - 11 May
6 Mi to Salisbury: Forest-view Sanctuary!

Safari Apartments

Safari Apartments
3.0 star property
Downtown Ocean City
9.2 out of 10, Wonderful, (35 reviews)
"Great place to stay and very close to the boardwalk. "
United States
Dawn J
The price is AU$282
includes taxes & fees
23 Apr - 24 Apr
Safari Apartments

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$281
includes taxes & fees
4 May - 5 May
ELIS APARTMENT

On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.2 out of 10, Wonderful, (30 reviews)
"We loved everything about our stay! This place is adorable and the location is awesome!"
United States
kelly K.
The price is AU$352
includes taxes & fees
4 May - 5 May
On Main Street - Apartment C - Berlin, MD

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
The price is AU$224
includes taxes & fees
22 Apr - 23 Apr
First Floor Studio Apartment in Historic Chestertown

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is AU$391
includes taxes & fees
26 Apr - 27 Apr
Historic Chesapeake City Stay

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, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is AU$177
includes taxes & fees
27 Apr - 28 Apr
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, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is AU$384
includes taxes & fees
28 Apr - 29 Apr
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 stay, would do it again."
United States
Brandon D.
The price is AU$349
includes taxes & fees
22 Apr - 23 Apr
Charming Coastal/Country Home w/3 Acres & Sauna!

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, (44 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$441
includes taxes & fees
27 Apr - 28 Apr
Comfortable cottage in gated community, 5 mins to OC and Assateague

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (53 reviews)
"Great little place "
United States
Eric R.
The price is AU$263
includes taxes & fees
26 Apr - 27 Apr
Cottage near the Bay

Ocean calling & country concert availability!

Ocean calling & country concert availability!
North Ocean City
9.0 out of 10, Wonderful, (35 reviews)
"We really enjoyed our stay here! Close to the beach and in walking distance of a lot of activities but also very quiet! Loved it!"
United States
Renee P.
The price is AU$288
includes taxes & fees
22 Apr - 23 Apr
Ocean calling & country concert availability!

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"This place is out in the country, but a short distance to lots of places we wanted to see, shop at, visit."
United States
Richard
The price is AU$158
includes taxes & fees
28 Apr - 29 Apr
Country Get Away Studio Apartment

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, (18 reviews)
"Property was nice and clean"
United States
Luke S.
The price is AU$403
includes taxes & fees
22 May - 23 May
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Clean, modern and well-equipped Ocean City condo

Clean, modern and well-equipped Ocean City condo
Downtown Ocean City
10.0 out of 10, Exceptional, (16 reviews)
"Place was very clean! Will stay again! "
United States
Rebecca M.
The price is AU$361
includes taxes & fees
22 Apr - 23 Apr
Clean, modern and well-equipped Ocean City condo

Wilmington Terrace

Wilmington Terrace
3.0 star property
Downtown Ocean City
8.4 out of 10, Very good, (10 reviews)
"Very clean and close to beach"
United States
Tony
The price is AU$257
includes taxes & fees
4 May - 5 May
Wilmington Terrace

Waterfront 2 Bedroom - 2 Blocks from the Beach - Premium Location

Waterfront 2 Bedroom - 2 Blocks from the Beach - Premium Location
North Ocean City
9.4 out of 10, Exceptional, (42 reviews)
"We had a great week. Loved being on the bayside and having the pier. The place is a quick and easy walk to the beach. The kids loved the bunk room. Great place for families to stay "
United States
Jennifer C.
The price is AU$451
includes taxes & fees
28 Apr - 29 Apr
Waterfront 2 Bedroom - 2 Blocks from the Beach - Premium Location

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, (19 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is AU$399
includes taxes & fees
22 Apr - 23 Apr
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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$164 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.