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

Eastern Shore Vacation Rentals

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Our top choices for Eastern Shore vacation rentals

1. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.2 out of 10, Wonderful, (360 reviews)
"Great Place, so cute! Our daughter had the best time at the pool, its quiet kids are able to run around and just have a great time! its so relaxing there! Definitely will be coming back!"
United States
Kathryne
The price is CA $116
CA $154 total
includes taxes & fees
Sep 13 - Sep 14
Shore Point Cottages

2. 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
The price is CA $110
CA $123 total
includes taxes & fees
Sep 14 - Sep 15
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

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.
The price is CA $177
CA $453 total
includes taxes & fees
Aug 26 - Aug 27
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

4. 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 $344 total
includes taxes & fees
Sep 1 - Sep 2
Salisbury Riverfront Lofts

5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (123 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is CA $136
CA $219 total
includes taxes & fees
Sep 1 - Sep 2
First Floor Studio Apartment in Historic Chestertown

6. 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.
The price is CA $171
CA $404 total
includes taxes & fees
Aug 29 - Aug 30
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

7. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (488 reviews)
"Great location--Very close to the steps and boardwalk!"
United States
ALEXIS
The price is CA $110
CA $130 total
includes taxes & fees
Sep 1 - Sep 2
Majestic Hotel & Apartments

8. 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.
The price is CA $170
CA $443 total
includes taxes & fees
Aug 27 - Aug 28
Charming Coastal/Country Home w/3 Acres & Sauna!

9. 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
The price is CA $158
CA $284 total
includes taxes & fees
Sep 20 - Sep 21
Safari Apartments

10. 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.
The price is CA $213
CA $347 total
includes taxes & fees
Aug 26 - Aug 27
Sailwinds Loft at Cambridge Creek

11. 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.
The price is CA $94
CA $172 total
includes taxes & fees
Sep 9 - Sep 10
Guest Suite for up to 2 in a Victorian on the Chester River

12. 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.
The price is CA $149
CA $385 total
includes taxes & fees
Aug 26 - Aug 27
Historic Chesapeake City Stay

13. 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.
The price is CA $96
CA $153 total
includes taxes & fees
Aug 31 - Sep 1
Country Get Away Studio Apartment

14. 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
The price is CA $148
CA $341 total
includes taxes & fees
Sep 13 - Sep 14
ELIS APARTMENT

15. 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
9.8 out of 10, Exceptional, (23 reviews)
"First time using VRBO and it was more than inexpected"
United States
Robert J.
The price is CA $101
CA $253 total
includes taxes & fees
Sep 22 - Sep 23
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

16. Boardwalk Terrace Apartments

Boardwalk Terrace Apartments
3.0 star property
Downtown Ocean City
5.8 out of 10, (110 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
The price is CA $117
CA $136 total
includes taxes & fees
Sep 23 - Sep 24
Boardwalk Terrace Apartments

17. 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.
The price is CA $248
CA $394 total
includes taxes & fees
Sep 19 - Sep 20
BAYSIDE BUNGALOW

18. 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
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is CA $165
CA $222 total
includes taxes & fees
Aug 26 - Aug 27
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

19. 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
The price is CA $275
CA $579 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is CA $182
CA $373 total
includes taxes & fees
Aug 26 - Aug 27
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

Find out more about Eastern Shore

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Eastern Shore. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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