Eastern Shore Vacation Rentals

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Our top choices for Eastern Shore vacation rentals

Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Coconut Malorie Resort Ocean City, Ascend Collection Hotel
3.0 star property
Midtown Ocean City
7.4 out of 10, Good, (1,306 reviews)
"The room was dirty "
United States
Kayleigh
The price is CA $134
CA $168 total
includes taxes & fees
Jun 8 - Jun 9
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Majestic Hotel & Apartments

Majestic Hotel & Apartments
3.0 star property
Downtown Ocean City
6.2 out of 10, (350 reviews)
"Clean and very friendly staff"
United States
Randy
The price is CA $140
CA $191 total
includes taxes & fees
May 25 - May 26
Majestic Hotel & Apartments

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
8.8 out of 10, Excellent, (3 reviews)
"Very nice cabin. By the town and easy drive to everything. "
United States
Mark
The price is CA $478
CA $579 total
includes taxes & fees
May 14 - May 15
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Boardwalk One

Boardwalk One
3.0 star property
Downtown Ocean City
7.4 out of 10, Good, (171 reviews)
"Close to boardwalk, beach, shopping and dining. Also it was very affordable."
United States
ANGELA
The price is CA $256
CA $302 total
includes taxes & fees
May 12 - May 13
Boardwalk One

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, (251 reviews)
"Great location and clean!"
United States
Susan V.
The price is CA $198
CA $381 total
includes taxes & fees
May 10 - May 11
Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (53 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is CA $246
CA $381 total
includes taxes & fees
May 13 - May 14
BAYSIDE BUNGALOW

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (24 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is CA $92
CA $341 total
includes taxes & fees
May 10 - May 11
Salisbury Riverfront Lofts

The Mallard Apartments

The Mallard Apartments
2.5 star property
Downtown Ocean City
6.0 out of 10, (42 reviews)
"It was a really nice and unique place to stay but windows were broken and didn’t have screens. The tv also did not work."
United States
Kaci
The price is CA $135
CA $172 total
includes taxes & fees
May 12 - May 13
The Mallard Apartments

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, (21 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is CA $93
CA $171 total
includes taxes & fees
May 14 - May 15
Guest Suite for up to 2 in a Victorian on the Chester River

Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!

Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!
North Ocean City
10.0 out of 10, Exceptional, (102 reviews)
"We had a wonderful time and enjoyed the lovely view! It was very clean and beautiful we are looking forward to going back!"
United States
Phonisha W.
The price is CA $445
CA $803 total
includes taxes & fees
May 25 - May 26
Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay
3.0 star property
Midtown Ocean City
8.4 out of 10, Very good, (39 reviews)
"One of the cleanest places I’ve stay at loved it ! "
United States
Kelsey
The price is CA $148
CA $403 total
includes taxes & fees
May 10 - May 11
Bay Club Resort by Coolvacay

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
The price is CA $135
CA $217 total
includes taxes & fees
May 13 - May 14
First Floor Studio Apartment in Historic Chestertown

The Escape at the Beach

The Escape at the Beach
North Ocean City
The price is CA $286
CA $709 total
includes taxes & fees
May 17 - May 18
The Escape at the Beach

Safari Apartments

Safari Apartments
3.0 star property
Downtown Ocean City
9.2 out of 10, Wonderful, (35 reviews)
"Great place to stay and very close to the boardwalk. "
United States
Dawn J
The price is CA $122
CA $277 total
includes taxes & fees
May 12 - May 13
Safari Apartments

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (54 reviews)
"Great little place "
United States
Eric R.
The price is CA $111
CA $257 total
includes taxes & fees
May 10 - May 11
Cottage near the Bay

Comfortable cottage in gated community, 5 mins to OC and Assateague

Comfortable cottage in gated community, 5 mins to OC and Assateague
Assateague Pointe
9.8 out of 10, Exceptional, (45 reviews)
"great place, great location, safe secure and everything we needed to get to assateague where the rest of the family were camping"
United States
Thomas B.
The price is CA $184
CA $497 total
includes taxes & fees
May 13 - May 14
Comfortable cottage in gated community, 5 mins to OC and Assateague

Mid Town OceanSide/Block 46th St. Sleeps 5 Location, Location, Location!

Mid Town OceanSide/Block 46th St. Sleeps 5 Location, Location, Location!
Midtown Ocean City
9.0 out of 10, Wonderful, (123 reviews)
"Perfect location. Clean and safe. Thanks for a great stay! "
United States
Kelly G.
The price is CA $273
CA $462 total
includes taxes & fees
May 12 - May 13
Mid Town OceanSide/Block 46th St. Sleeps 5 Location, Location, Location!

Oceanfront and Bay view at the Carousel with indoor pool

Oceanfront and Bay view at the Carousel with indoor pool
North Ocean City
9.8 out of 10, Exceptional, (310 reviews)
"It was a wonderful stay! Beds were comfortable, the kitchen was well stocked, and the views were unbeatable!"
United States
Kim W.
The price is CA $198
CA $512 total
includes taxes & fees
May 11 - May 12
Oceanfront and Bay view at the Carousel with indoor pool

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
10.0 out of 10, Exceptional, (42 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is CA $240
CA $289 total
includes taxes & fees
May 10 - May 11
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

OCHG VIRGINIA LEE

OCHG VIRGINIA LEE
2.0 star property
Downtown Ocean City
7.8 out of 10, Good, (8 reviews)
"Love the quaintness of the property. Very clean. Needs updating however did have the old school beach vibe. Really enjoyed our stay. "
United States
Kimberly
The price is CA $246
CA $593 total
includes taxes & fees
May 21 - May 22
OCHG VIRGINIA LEE
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.