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

Eastern Shore Holiday Rentals

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Check prices for these dates

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

Our top choices for Eastern Shore holiday 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 HK$604
HK$676 total
includes taxes & fees
17 Oct - 18 Oct
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

2. 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 HK$835
HK$2,440 total
includes taxes & fees
5 Oct - 6 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

3. 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 HK$973
HK$2,204 total
includes taxes & fees
4 Oct - 5 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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.
The price is HK$706
HK$2,105 total
includes taxes & fees
8 Oct - 9 Oct
Cass-N-Reel Luxury Houseboat
A lighthouse with a white exterior, a balcony, and a metal roof.

5. 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 HK$747
HK$2,310 total
includes taxes & fees
4 Oct - 5 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
A modern exterior with a black door, a metal staircase, and a lantern.

6. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (108 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
Cass-Away Luxury Houseboat
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

7. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (128 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 HK$777
HK$1,246 total
includes taxes & fees
1 Oct - 2 Oct
First Floor Studio Apartment in Historic Chestertown
A bunk bed room with white bedding and blue throw blankets.

8. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is HK$2,853
HK$3,024 total
includes taxes & fees
13 Oct - 14 Oct
Bohemia Manor Farm
A room with a large bed, multiple windows, and a ceiling fan.

9. 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 HK$526
HK$1,959 total
includes taxes & fees
1 Oct - 2 Oct
Salisbury Riverfront Lofts
A riverside dock with boats, a covered seating area, and a bridge in the background.

10. 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 HK$847
HK$2,187 total
includes taxes & fees
1 Oct - 2 Oct
Historic Chesapeake City Stay
A building with a gabled roof and a circular vent on the roof.

11. 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 HK$1,569
HK$2,476 total
includes taxes & fees
1 Oct - 2 Oct
BAYSIDE BUNGALOW
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

12. 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 HK$1,295
HK$2,977 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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 HK$533
HK$981 total
includes taxes & fees
1 Oct - 2 Oct
Guest Suite for up to 2 in a Victorian on the Chester River
An open door leading to a bedroom with a bed, a nightstand, and a lamp.

14. 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 HK$549
HK$1,409 total
includes taxes & fees
4 Oct - 5 Oct
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

15. 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 HK$1,216
HK$1,913 total
includes taxes & fees
1 Oct - 2 Oct
Sailwinds Loft at Cambridge Creek
A living room with a sofa, ottoman, and a lamp. There is a television mounted on the wall and a window with blinds.

16. Pool + Bay Access! Home 13 Mi to Ocean City Beach

Pool + Bay Access! Home 13 Mi to Ocean City Beach
3.0 star property
Ocean Pines
The price is HK$745
HK$3,361 total
includes taxes & fees
1 Oct - 2 Oct
Pool + Bay Access! Home 13 Mi to Ocean City Beach
A residential house with a brick exterior, a dark roof, and a front porch with a bench.

17. 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 HK$941
HK$1,264 total
includes taxes & fees
1 Oct - 2 Oct
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

18. 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 HK$1,255
HK$2,935 total
includes taxes & fees
6 Oct - 7 Oct
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A balcony with a view of a parking lot and buildings.

19. Americana Condos 10th street

Americana Condos 10th street
3.5 star property
Downtown Ocean City
8.4 out of 10, Very good, (33 reviews)
"Wonderful views and so big!"
United States
Liz
The price is HK$1,299
HK$3,652 total
includes taxes & fees
31 Oct - 1 Nov
Americana Condos 10th street
A beachside table with a decorative centerpiece, two lanterns, and a view of the ocean.

20. BeachBox III • Unreal Views • Oceanfront Balcony • Couple's Getaway

BeachBox III • Unreal Views • Oceanfront Balcony • Couple's Getaway
Midtown Ocean City
10.0 out of 10, Exceptional, (25 reviews)
"A true gem! Perfect location, excellent accommodations, and quick, friendly communication from the host. We had a wonderful stay and would happily return."
United States
Bethzaida
The price is HK$1,087
HK$2,746 total
includes taxes & fees
14 Oct - 15 Oct
BeachBox III • Unreal Views • Oceanfront Balcony • Couple's Getaway
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

8/10 Good
"Front desk was awesome. Room needs a little upkeep. Great view of the beach and Coconuts was a great little spot for live music"
Chad 3-night trip
Posted 4 hours ago
Castle in the Sand

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