A marina with numerous boats docked at wooden piers under a clear sky.

Eastern Shore Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Eastern Shore vacation rentals

A gym with treadmills, dumbbells, and exercise balls, large windows with a view of the ocean.

1. Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
3.0 star property
Midtown Ocean City
7.4 out of 10, Good, (1,327 reviews)
"Our room.seemed to be all new and we loved how there was a separate living room and bedroom with privacy doors. We had a beautiful view of the bay too from the second floor and we loved being on the sunset side of OC:)"
United States
cara
The price is CA $124
CA $139 total
includes taxes & fees
Oct 12 - Oct 13
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
A room with a large bed, multiple windows, and a ceiling fan.

2. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (27 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
The price is CA $92
CA $352 total
includes taxes & fees
Nov 10 - Nov 11
Salisbury Riverfront Lofts
A living room with two grey sofas, a coffee table, and a ceiling fan.

3. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
The price is CA $135
CA $459 total
includes taxes & fees
Oct 19 - Oct 20
Cambridge Apt in Walkable Neighborhood
A modern kitchen with dark cabinets, a white countertop, and a large window.

4. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
Cass-N-Reel Luxury Houseboat
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

5. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is CA $167
CA $465 total
includes taxes & fees
Oct 19 - Oct 20
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

6. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"
United States
Charr
The price is CA $141
CA $226 total
includes taxes & fees
Oct 12 - Oct 13
First Floor Studio Apartment in Historic Chestertown
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

7. 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
9.8 out of 10, Exceptional, (29 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 CA $97
CA $178 total
includes taxes & fees
Oct 19 - Oct 20
Guest Suite for up to 2 in a Victorian on the Chester River
A riverside dock with boats, a covered seating area, and a bridge in the background.

8. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (30 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
The price is CA $154
CA $400 total
includes taxes & fees
Oct 15 - Oct 16
Historic Chesapeake City Stay
A covered patio with a table and chairs, overlooking a beach.

9. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (530 reviews)
"Very bice"
United States
Robert
The price is CA $91
CA $109 total
includes taxes & fees
Oct 13 - Oct 14
Majestic Hotel & Apartments
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is CA $114
CA $398 total
includes taxes & fees
Oct 14 - Oct 15
Charming Coastal/Country Home w/3 Acres & Sauna!
A beachside boardwalk with shops, a Ferris wheel, and a tram.

11. On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (43 reviews)
"A perfect location if you want to explore downtown Berlin. It’s right in the heart of Main Street walking distance to everything.The apartment had everything we needed and was very cozy and clean . Would definitely book this spot again."
United States
Sarah V.
The price is CA $102
CA $331 total
includes taxes & fees
Oct 18 - Oct 19
On Main Street - Apartment C - Berlin, MD
A multi-story building with a white exterior, balconies, and a sign indicating it is an apartment complex.

12. Ocean Terrace Family Apartments

Ocean Terrace Family Apartments
3.0 star property
Downtown Ocean City
7.6 out of 10, Good, (64 reviews)
"There isn’t a lot if parking for the property but besides that it was great"
United States
Pamela
The price is CA $101
CA $114 total
includes taxes & fees
Oct 11 - Oct 12
Ocean Terrace Family Apartments
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

13. 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is CA $168
CA $410 total
includes taxes & fees
Oct 12 - Oct 13
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A modern kitchen with white cabinets, a central island, and a dining area with a wooden table and chairs.

14. Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!

Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!
Midtown Ocean City
9.8 out of 10, Exceptional, (274 reviews)
"Great spot, clean and affordable!"
United States
Beth H.
The price is CA $119
CA $285 total
includes taxes & fees
Nov 1 - Nov 2
Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!
A covered patio with a table and chairs, a sliding glass door, and a white fence.

15. Monte Carlo Condos

Monte Carlo Condos
3.0 star property
Downtown Ocean City
7.0 out of 10, Good, (74 reviews)
"Unexpected pet fee on top of resort fees we did expect. Nice and close to boardwalk. Room was quiet, private, spacious."
United States
Ben
The price is CA $117
CA $306 total
includes taxes & fees
Oct 26 - Oct 27
Monte Carlo Condos
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

16. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (14 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is CA $242
CA $547 total
includes taxes & fees
Nov 3 - Nov 4
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A covered porch with wooden flooring, white railings, and two green chairs.

17. Wilmington Terrace

Wilmington Terrace
3.0 star property
Downtown Ocean City
8.2 out of 10, Very good, (12 reviews)
"The staff was very friendly, the apartment was very clean, I love that pets are welcome and the beach and boardwalk are less than 2 minutes walk. EXCELLENT!"
United States
Jennifer
The price is CA $166
CA $300 total
includes taxes & fees
Oct 11 - Oct 12
Wilmington Terrace
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

18. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is CA $220
CA $362 total
includes taxes & fees
Oct 18 - Oct 19
Sailwinds Loft at Cambridge Creek
A building with a gabled roof and a circular vent on the roof.

19. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (66 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is CA $284
CA $449 total
includes taxes & fees
Oct 12 - Oct 13
BAYSIDE BUNGALOW
A room with teal walls, a gray sofa, a white dresser, and a ceiling fan.

20. Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N

Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
North Ocean City
9.2 out of 10, Wonderful, (54 reviews)
"check in/check out were super simple. place was clean, but a little tight for 5. location is great."
United States
Theodore B.
The price is CA $90
CA $295 total
includes taxes & fees
Oct 12 - Oct 13
Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Eastern Shore Hotel Reviews

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"Great view of the water and nice facility!"
Sarah 3-night trip
Posted 3 hours ago
Princess Royale Oceanfront Resort

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Eastern Shore vacation rentals we have selected for you start as low as CA $114 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 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. 

Explore a world of travel with Expedia