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
9.4 out of 10, Exceptional, (403 reviews)
"Everything was clean and comfortable. Would stay here again."
United States
Kelly
$104 nightly
The price is $117
Nov 10 - Nov 11
Total with taxes and fees
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, (1,331 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
$92 nightly
The price is $103
Nov 28 - Nov 29
Total with taxes and fees
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

3. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (28 reviews)
"I loved the location, the cleanliness and how good I felt being there. Thank you"
United States
Carmen
$242 nightly
The price is $261
Nov 8 - Nov 9
Total with taxes and fees
Salisbury Riverfront Lofts

4. 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
$291 nightly
The price is $323
Nov 8 - Nov 9
Total with taxes and fees
Cambridge Apt in Walkable Neighborhood

5. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
$226 nightly
The price is $250
Nov 12 - Nov 13
Total with taxes and fees
Cass-N-Reel Luxury Houseboat

6. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$133 nightly
The price is $147
Nov 9 - Nov 10
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
$108 nightly
The price is $114
Nov 9 - Nov 10
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River

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

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.2 out of 10, Wonderful, (44 reviews)
"Great location and very cozy. I wish we could’ve stayed longer."
United States
Christopher W.
$201 nightly
The price is $225
Nov 9 - Nov 10
Total with taxes and fees
On Main Street - Apartment C - Berlin, MD

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
$270 nightly
The price is $291
Nov 9 - Nov 10
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!

10. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"Cute place. Clean, comfortable, and convenient to the soccer complex. I wasn’t familiar with Chesapeake City but we had a great time at the waterfront restaurants."
United States
John P.
$270 nightly
The price is $286
Nov 8 - Nov 9
Total with taxes and fees
Historic Chesapeake City Stay

11. 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, (275 reviews)
"Great place right by the ocean."
United States
Ben P.
$176 nightly
The price is $197
Nov 11 - Nov 12
Total with taxes and fees
Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!

12. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (52 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
$97 nightly
The price is $103
Nov 16 - Nov 17
Total with taxes and fees
Country Get Away Studio Apartment

13. 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, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
$359 nightly
The price is $381
Nov 30 - Dec 1
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

14. Canal front with boat slip, boat ramp, WiFi, and roku streaming TV

Canal front with boat slip, boat ramp, WiFi, and roku streaming TV
Midtown Ocean City
9.8 out of 10, Exceptional, (10 reviews)
"Really cute place in a great location!"
United States
Mindie F.
$137 nightly
The price is $153
Nov 9 - Nov 10
Total with taxes and fees
Canal front with boat slip, boat ramp, WiFi, and roku streaming TV

15. 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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$253 nightly
The price is $280
Nov 12 - Nov 13
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

16. 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.
$228 nightly
The price is $242
Nov 8 - Nov 9
Total with taxes and fees
Sailwinds Loft at Cambridge Creek

17. 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)
"Very friendly!"
United States
Anonymous traveler
$176 nightly
The price is $197
Nov 9 - Nov 10
Total with taxes and fees
Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N

18. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
Denton
10.0 out of 10, Exceptional, (15 reviews)
"The house was perfect, welcoming and comfortable, will be coming back again"
United States
Dallas S.
$320 nightly
The price is $339
Dec 1 - Dec 2
Total with taxes and fees
Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

19. BeachBox® III • Unreal Views • Oceanfront Balcony • Worcester House 401

BeachBox® III • Unreal Views • Oceanfront Balcony • Worcester House 401
Midtown Ocean City
10.0 out of 10, Exceptional, (30 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
$202 nightly
The price is $226
Nov 9 - Nov 10
Total with taxes and fees
BeachBox® III • Unreal Views • Oceanfront Balcony • Worcester House 401

20. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
$315 nightly
The price is $341
Nov 23 - Nov 24
Total with taxes and fees
Relax on Kent Island in 4 Bedroom Home w/Waterview
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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