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. 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, (1,321 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 $102
CA $114 total
includes taxes & fees
Oct 16 - Oct 17
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

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 CA $124
CA $403 total
includes taxes & fees
Sep 23 - Sep 24
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 CA $165
CA $400 total
includes taxes & fees
Sep 23 - Sep 24
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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 CA $140
CA $395 total
includes taxes & fees
Oct 8 - Oct 9
Cass-N-Reel Luxury Houseboat

5. 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.
The price is CA $126
CA $425 total
includes taxes & fees
Sep 28 - Sep 29
Cass-Away Luxury Houseboat

6. 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 CA $133
CA $599 total
includes taxes & fees
Sep 23 - Sep 24
Pool + Bay Access! Home 13 Mi to Ocean City Beach

7. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (29 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 $151
CA $391 total
includes taxes & fees
Sep 23 - Sep 24
Historic Chesapeake City Stay

8. 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 $252
CA $559 total
includes taxes & fees
Sep 28 - Sep 29
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9. 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 CA $95
CA $175 total
includes taxes & fees
Sep 28 - Sep 29
Guest Suite for up to 2 in a Victorian on the Chester River

10. 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 CA $203
CA $619 total
includes taxes & fees
Oct 18 - Oct 19
Americana Condos 10th street

11. 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 $89
CA $345 total
includes taxes & fees
Oct 23 - Oct 24
Salisbury Riverfront Lofts

12. 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 CA $217
CA $356 total
includes taxes & fees
Sep 23 - Sep 24
Sailwinds Loft at Cambridge Creek

13. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is CA $138
CA $222 total
includes taxes & fees
Sep 29 - Sep 30
First Floor Studio Apartment in Historic Chestertown

14. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (515 reviews)
"Very bice"
United States
Robert
The price is CA $99
CA $118 total
includes taxes & fees
Oct 13 - Oct 14
Majestic Hotel & Apartments

15. 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 CA $186
CA $484 total
includes taxes & fees
Sep 28 - Sep 29
Charming Coastal/Country Home w/3 Acres & Sauna!

16. 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 $231
CA $465 total
includes taxes & fees
Sep 23 - Sep 24
ELIS APARTMENT

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 CA $98
CA $251 total
includes taxes & fees
Sep 28 - Sep 29
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

18. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (65 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is CA $280
CA $440 total
includes taxes & fees
Sep 23 - Sep 24
BAYSIDE BUNGALOW

19. 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 CA $252
CA $557 total
includes taxes & fees
Sep 23 - Sep 24
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

20. Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!

Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!
Midtown Ocean City
9.8 out of 10, Exceptional, (18 reviews)
"Very friendly and helpful host! The room was lovely and very clean when we arrived. We would stay with this host again."
United States
Hannah
The price is CA $94
CA $323 total
includes taxes & fees
Sep 23 - Sep 24
Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!
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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