Eastern Shore Vacation Rentals

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Jan 11 - Jan 12
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Jan 12 - Jan 13
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Jan 16 - Jan 18
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Jan 23 - Jan 25

Our top choices for Eastern Shore vacation rentals

Deluxe Cottage | View from room
Shore Point Cottages

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
$124 nightly
The price is $139
Jan 13 - Jan 14
Total with taxes and fees
Shore Point Cottages
Exterior
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

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, (1,298 reviews)
"Scenic area with wonderful wooden bridges and view of water. There was no hot water to shower, but not a deal breaker."
United States
Isolda
$87 nightly
The price is $98
Feb 10 - Feb 11
Total with taxes and fees
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
Smart TV
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

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
2.0 star property
Elkton
9.8 out of 10, Exceptional, (8 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
$152 nightly
The price is $161
Jan 17 - Jan 18
Total with taxes and fees
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Apartment D: Riverfront Grand | 2 bedrooms, individually decorated, individually furnished
Salisbury Riverfront Lofts

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
$242 nightly
The price is $261
Jan 13 - Jan 14
Total with taxes and fees
Salisbury Riverfront Lofts
Outdoor pool
Comfortable cottage in gated community, 5 mins to OC and Assateague

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)
"This was the perfect little home for our stay. Everything was clean and comfortable and “cozy”. The location was wonderful with easy access to both Assateague Island and Ocean City. Everything needed for a great stay was provided. We are already planning our vacation for next year and will definitely book again. "
United States
Alecia C.
$286 nightly
The price is $320
Jan 13 - Jan 14
Total with taxes and fees
Comfortable cottage in gated community, 5 mins to OC and Assateague
Smart TV, foosball, books
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
2.0 star property
Chesapeake City
9.4 out of 10, Exceptional, (3 reviews)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
$316 nightly
The price is $335
Jan 12 - Jan 13
Total with taxes and fees
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Smart TV, books
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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
10.0 out of 10, Exceptional, (34 reviews)
"What a cozy place to stay! The best part was in the morning when you can see the beautiful morning sky from the bed in the loft, the sun eloquently shining in through the windows and the deer frolicking in the yard. Comfy beds and plenty of lighting, would love to stay again."
United States
Bobbijo B.
$196 nightly
The price is $207
Jan 12 - Jan 13
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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)
"Clean, comfortable and convenient! "
United States
Jill J.
$257 nightly
The price is $284
Jan 12 - Jan 13
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Exterior
Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
$105 nightly
The price is $111
Jan 19 - Jan 20
Total with taxes and fees
Country Get Away 1 Bedroom Apartment
Interior
Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (29 reviews)
"Was perfect for just husband and wife, one night stay to check out all the little shops, bars, restaurants (mostly in Havre de Grace) No kitchen really just fridge, microwave, keurig coffee (not a fan of that coffee) but was a really nice coffee shop within walking distance. A very cute, comfy place."
United States
Stephen C B.
$237 nightly
The price is $251
Jan 12 - Jan 13
Total with taxes and fees
Private 3 room Queen Suite w/Kitchenette
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"The place was wonderful beautiful views of harbor, extremely clean and well appointed. Great restaurants we ate at RAR, great beer and food. Christopher’ Corner great dinner food fabulous and cocktails, highly recommend. Blackwater Cafe wonderful breakfast. "
United States
deb j.
$327 nightly
The price is $347
Jan 12 - Jan 13
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
2.0 star property
Downtown Cambridge
9.8 out of 10, Exceptional, (11 reviews)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
$310 nightly
The price is $329
Feb 2 - Feb 3
Total with taxes and fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Fridge, microwave, oven, stovetop
Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (11 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$198 nightly
The price is $210
Jan 12 - Jan 13
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
Marina
Historic Chesapeake City Stay

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.
$263 nightly
The price is $279
Jan 12 - Jan 13
Total with taxes and fees
Historic Chesapeake City Stay
Beach
Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
$285 nightly
The price is $315
Jan 12 - Jan 13
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Property grounds
First Floor Studio Apartment in Historic Chestertown

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.
$144 nightly
The price is $159
Jan 12 - Jan 13
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop
Charming 2-Bed Condo Steps From the Beach!

Charming 2-Bed Condo Steps From the Beach!

Charming 2-Bed Condo Steps From the Beach!
North Ocean City
10.0 out of 10, Exceptional, (32 reviews)
"Great location, place very clean and perfect for our trip!"
United States
Ed S.
$304 nightly
The price is $338
Jan 12 - Jan 13
Total with taxes and fees
Charming 2-Bed Condo Steps From the Beach!
City view
Americana Condos 10th street

Americana Condos 10th street

Americana Condos 10th street
3.5 star property
Downtown Ocean City
8.4 out of 10, Very Good, (19 reviews)
"straight fire, definitely going back"
United States
stephen
$418 nightly
The price is $469
Feb 6 - Feb 7
Total with taxes and fees
Americana Condos 10th street
Exterior
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

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.
$118 nightly
The price is $125
Jan 22 - Jan 23
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Marina
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
2.5 star property
Downtown Cambridge
10.0 out of 10, Exceptional, (10 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
$320 nightly
The price is $339
Jan 12 - Jan 13
Total with taxes and fees
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
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

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

10/10 Excellent
"The hotel and suites are very clean . It was stocked with your basic essentials."
Latanya 3-night trip
Posted 2 days ago
Holiday Inn & Suites Ocean City by IHG

Find out more about Eastern Shore

Everything you need to know about Eastern Shore vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Eastern Shore vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Eastern Shore vacation 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 low season months. For more hustle and bustle, you may prefer to visit Eastern Shore in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $98 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Eastern Shore rentals

At Expedia, we put the best Eastern Shore vacation 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 vacation.

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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