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

Eastern Shore Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Eastern Shore vacation rentals

Deluxe Cottage | View from room

1. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (364 reviews)
"Good and cute environment"
United States
junghyun
$104 nightly
The price is $117
Sep 13 - Sep 14
Total with taxes and fees
Shore Point Cottages
Apartment D: Riverfront Grand | 2 bedrooms, iron/ironing board (on request), WiFi (free)

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
$238 nightly
The price is $256
Aug 30 - Aug 31
Total with taxes and fees
Salisbury Riverfront Lofts
Exterior

3. 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.
$255 nightly
The price is $275
Aug 30 - Aug 31
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Fitness facility

4. 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, (1,317 reviews)
"The hotel did not disappoint. The room, the tub and especially the shower was the best. We also loved the view. Would come back again and get the same room. We had the presidential suite."
United States
Nichole
$80 nightly
The price is $90
Sep 14 - Sep 15
Total with taxes and fees
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
$256 nightly
The price is $276
Aug 31 - Sep 1
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Property grounds

6. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (124 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
$144 nightly
The price is $159
Sep 2 - Sep 3
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Interior

7. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (107 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
$285 nightly
The price is $315
Sep 25 - Sep 26
Total with taxes and fees
Cass-Away Luxury Houseboat
Beach

8. 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, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$261 nightly
The price is $288
Aug 30 - Aug 31
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Private kitchen

9. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (38 reviews)
"Wonderful place to stay."
United States
Sharon D.
$240 nightly
The price is $254
Aug 30 - Aug 31
Total with taxes and fees
Sailwinds Loft at Cambridge Creek
Comfort Apartment | Terrace/patio

10. Safari Apartments

Safari Apartments
3.0 star property
Downtown Ocean City
9.4 out of 10, Exceptional, (42 reviews)
"Clean and quiet"
United States
LATONUIA P
$193 nightly
The price is $216
Sep 20 - Sep 21
Total with taxes and fees
Safari Apartments
Marina

11. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
$366 nightly
The price is $388
Sep 1 - Sep 2
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Exterior

12. 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, (27 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.
$118 nightly
The price is $125
Sep 9 - Sep 10
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Marina

13. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (28 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.
$267 nightly
The price is $283
Aug 30 - Aug 31
Total with taxes and fees
Historic Chesapeake City Stay
Exterior

14. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (47 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
$105 nightly
The price is $111
Sep 9 - Sep 10
Total with taxes and fees
Country Get Away Studio Apartment
Deluxe Apartment, 4 Bedrooms, Non Smoking, Ocean View | Terrace/patio

15. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (489 reviews)
"Great location--Very close to the steps and boardwalk!"
United States
ALEXIS
$93 nightly
The price is $105
Sep 1 - Sep 2
Total with taxes and fees
Majestic Hotel & Apartments
Exterior detail

16. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
$263 nightly
The price is $290
Aug 30 - Aug 31
Total with taxes and fees
BAYSIDE BUNGALOW
Terrace/patio

17. Boardwalk Terrace Apartments

Boardwalk Terrace Apartments
3.0 star property
Downtown Ocean City
5.8 out of 10, (111 reviews)
"Staff was very professional and polite. Ocean veiw was amazing from the balcony. Room was clean and comfortable. Location was perfect for beach and shops and restaurants."
United States
Melissa
$73 nightly
The price is $81
Sep 29 - Sep 30
Total with taxes and fees
Boardwalk Terrace Apartments
City view

18. Americana Condos 10th street

Americana Condos 10th street
3.5 star property
Downtown Ocean City
8.4 out of 10, Very Good, (29 reviews)
"Wonderful views and so big!"
United States
Liz
$436 nightly
The price is $488
Sep 28 - Sep 29
Total with taxes and fees
Americana Condos 10th street
Family Apartment | Terrace/patio

19. ELIS APARTMENT

ELIS APARTMENT
3.0 star property
Downtown Ocean City
9.4 out of 10, Exceptional, (6 reviews)
"It was clean and comfortable very cool and quiet didn't have to use AC"
United States
Norda
$237 nightly
The price is $253
Sep 13 - Sep 14
Total with taxes and fees
ELIS APARTMENT
House (3 Bedrooms) | Front of property

20. 6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
$242 nightly
The price is $271
Aug 31 - Sep 1
Total with taxes and fees
6 Mi to Salisbury: Forest-view Sanctuary!
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

Castle in the Sand

Castle in the Sand

10/10 Excellent
"Rooms are a bit dated but everything else was great! Very convenient by beach and friendly staff."
Emilyn 1-night trip
Posted 1 hour ago
Castle in the Sand

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 $81 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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