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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (1,323 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 ￥12,113
￥13,567 total
includes taxes & fees
Oct 17 - Oct 18
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 ￥10,559
￥39,313 total
includes taxes & fees
Oct 4 - Oct 5
Salisbury Riverfront Lofts
A modern kitchen with dark cabinets, a white countertop, and a large window.

3. 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.
The price is ￥14,169
￥42,243 total
includes taxes & fees
Oct 8 - Oct 9
Cass-N-Reel Luxury Houseboat
A row of mobile homes with a one-way sign, a covered porch, and a street sign indicating 'Shore Point Lane'.

4. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (383 reviews)
"Easy accessible"
United States
Melissa
The price is ￥27,645
￥33,604 total
includes taxes & fees
Oct 2 - Oct 3
Shore Point Cottages
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (129 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 ￥15,580
￥24,997 total
includes taxes & fees
Oct 12 - Oct 13
First Floor Studio Apartment in Historic Chestertown
A lighthouse with a white exterior, a balcony, and a metal roof.

6. 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 ￥13,929
￥44,998 total
includes taxes & fees
Oct 4 - Oct 5
Charming Coastal/Country Home w/3 Acres & Sauna!
A riverside dock with boats, a covered seating area, and a bridge in the background.

7. 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 ￥16,996
￥43,872 total
includes taxes & fees
Oct 4 - Oct 5
Historic Chesapeake City Stay
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥19,514
￥46,213 total
includes taxes & fees
Oct 5 - Oct 6
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

9. 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 ￥13,929
￥45,498 total
includes taxes & fees
Oct 5 - Oct 6
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A beachside boardwalk with shops, a Ferris wheel, and a tram.

10. 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 ￥12,180
￥37,435 total
includes taxes & fees
Oct 7 - Oct 8
On Main Street - Apartment C - Berlin, MD
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

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
The price is ￥25,189
￥58,907 total
includes taxes & fees
Oct 27 - Oct 28
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A covered porch with wooden flooring, white railings, and two green chairs.

12. Wilmington Terrace

Wilmington Terrace
3.0 star property
Downtown Ocean City
8.2 out of 10, Very good, (12 reviews)
"Very clean and close to beach"
United States
Tony
The price is ￥18,384
￥33,180 total
includes taxes & fees
Oct 7 - Oct 8
Wilmington Terrace
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

13. 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, (28 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 ￥10,701
￥19,684 total
includes taxes & fees
Oct 5 - Oct 6
Guest Suite for up to 2 in a Victorian on the Chester River
A wooden cabin with a porch, surrounded by dense forest.

14. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (49 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is ￥11,016
￥17,515 total
includes taxes & fees
Oct 14 - Oct 15
Country Get Away Studio Apartment
A balcony with two chairs and a table, overlooking a beach with the ocean and a clear sky.

15. #1 Rated Condo, Oceanfront, with Bay View Too

#1 Rated Condo, Oceanfront, with Bay View Too
North Ocean City
10.0 out of 10, Exceptional, (341 reviews)
"Had a great stay "
United States
Ed B.
The price is ￥14,006
￥43,887 total
includes taxes & fees
Oct 7 - Oct 8
#1 Rated Condo, Oceanfront, with Bay View Too
A room with teal walls, a gray sofa, a white dresser, and a ceiling fan.

16. 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 ￥9,914
￥32,430 total
includes taxes & fees
Oct 13 - Oct 14
Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
An open door leading to a bedroom with a bed, a nightstand, and a lamp.

17. 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, (25 reviews)
"Great location with plenty of space to relax."
United States
Doug R.
The price is ￥11,016
￥28,264 total
includes taxes & fees
Oct 4 - Oct 5
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
A well-lit living room with a sofa, armchair, dining table, and a television.

18. Direct OceanFront Condo on the center of the Boardwalk Newly Remodeled with Pool

Direct OceanFront Condo on the center of the Boardwalk Newly Remodeled with Pool
Downtown Ocean City
9.6 out of 10, Exceptional, (83 reviews)
"Cozy. Great location!"
United States
Renee H.
Direct OceanFront Condo on the center of the Boardwalk Newly Remodeled with Pool
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

19. 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 ￥24,392
￥39,868 total
includes taxes & fees
Oct 6 - Oct 7
Sailwinds Loft at Cambridge Creek
A building with a gabled roof and a circular vent on the roof.

20. 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 ￥31,474
￥49,675 total
includes taxes & fees
Oct 4 - Oct 5
BAYSIDE BUNGALOW
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

Dunes Suites Oceanfront

Dunes Suites Oceanfront

10/10 Excellent
"I thought the room was very clean. The staff was very helpful."
Wilma 4-night trip
Posted 11 hours ago
Dunes Suites Oceanfront

Find out more about Eastern Shore

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