Holiday Rentals in Eastern Shore

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Our top choices for Eastern Shore holiday rentals

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

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 €83
includes taxes & fees
8 Mar - 9 Mar
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 €215
includes taxes & fees
8 Feb - 9 Feb
Salisbury Riverfront Lofts

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 €98
includes taxes & fees
16 Feb - 17 Feb
Country Get Away 1 Bedroom Apartment

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 €199
includes taxes & fees
9 Feb - 10 Feb
On Main Street - Apartment C - Berlin, MD

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 €272
includes taxes & fees
15 Feb - 16 Feb
Comfortable cottage in gated community, 5 mins to OC and Assateague

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.
The price is €110
includes taxes & fees
9 Feb - 10 Feb
Guest Suite for up to 2 in a Victorian on the Chester River

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is €240
includes taxes & fees
12 Feb - 13 Feb
Historic Chesapeake City Stay

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is €218
includes taxes & fees
7 Feb - 8 Feb
6 Mi to Salisbury: Forest-view Sanctuary!

Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo
Downtown Ocean City
9.8 out of 10, Exceptional, (62 reviews)
"Great location walking distance to everything. Thank you so much for a great stay."
United States
valerie0472
The price is €295
includes taxes & fees
9 Feb - 10 Feb
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is €245
includes taxes & fees
17 Feb - 18 Feb
Charming Coastal/Country Home w/3 Acres & Sauna!

Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway

Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway
North Ocean City
10.0 out of 10, Exceptional, (18 reviews)
"The condo is beautifully decorated and only steps from the beach! "
United States
Pamela H.
The price is €195
includes taxes & fees
8 Feb - 9 Feb
Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway

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 €141
includes taxes & fees
7 Feb - 8 Feb
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

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 €223
includes taxes & fees
8 Feb - 9 Feb
Deal Island Bay Cottage

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 €149
includes taxes & fees
9 Mar - 10 Mar
First Floor Studio Apartment in Historic Chestertown

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 €244
includes taxes & fees
7 Feb - 8 Feb
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Love Above the Waves - Best Ocean View & Heated Pool

Love Above the Waves - Best Ocean View & Heated Pool
North Ocean City
9.6 out of 10, Exceptional, (42 reviews)
"We enjoyed our stay. The place was nice and the view was awesome. "
United States
Ryan W.
The price is €201
includes taxes & fees
8 Feb - 9 Feb
Love Above the Waves - Best Ocean View & Heated Pool

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.6 out of 10, Exceptional, (5 reviews)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
United States
Rees L.
The price is €129
includes taxes & fees
7 Feb - 8 Feb
Summer Rustic Camping with AC and King Bed

Cozy Corner: Relax on an Amish Equestrian Farm

Cozy Corner: Relax on an Amish Equestrian Farm
Rising Sun
8.8 out of 10, Excellent, (3 reviews)
"We had a very nice stay at the farmhouse, it is an incredibly clean and well cared for property. We were in town for a fishing tournament with our truck/boat and there was plenty of room for parking as well. If you’re looking for a peaceful retreat, this is a great place!"
United States
Amy C.
Cozy Corner: Relax on an Amish Equestrian Farm

Ocean calling & country concert availability!

Ocean calling & country concert availability!
North Ocean City
9.0 out of 10, Wonderful, (35 reviews)
"Perfect place to stay for oceans calling! On bus route but not in the craziness of the direct festival area."
United States
Jennifer F.
The price is €180
includes taxes & fees
9 Feb - 10 Feb
Ocean calling & country concert availability!
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 €83 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.