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, (1,304 reviews)
"Everything was great :) Great location...great staff!"
United States
Daria
The price is CA $111
CA $141 total
includes taxes & fees
Mar 31 - Apr 1
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is CA $126
CA $353 total
includes taxes & fees
Mar 28 - Mar 29
6 Mi to Salisbury: Forest-view Sanctuary!

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (23 reviews)
"It was a great stay nice comfortable place "
United States
Adam
Salisbury Riverfront Lofts

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Every thing was great"
United States
lesia k.
The price is CA $136
CA $218 total
includes taxes & fees
Mar 26 - Mar 27
First Floor Studio Apartment in Historic Chestertown

Ocean calling & country concert availability!

Ocean calling & country concert availability!
North Ocean City
9.0 out of 10, Wonderful, (35 reviews)
"Perfect place to stay for oceans calling! On bus route but not in the craziness of the direct festival area."
United States
Jennifer F.
The price is CA $86
CA $284 total
includes taxes & fees
Mar 30 - Mar 31
Ocean calling & country concert availability!

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, (304 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 $100
CA $390 total
includes taxes & fees
Mar 29 - Mar 30
Oceanfront and Bay view at the Carousel with indoor pool

On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.2 out of 10, Wonderful, (29 reviews)
"We loved everything about our stay! This place is adorable and the location is awesome!"
United States
kelly K.
The price is CA $99
CA $317 total
includes taxes & fees
Mar 29 - Mar 30
On Main Street - Apartment C - Berlin, MD

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
9.6 out of 10, Exceptional, (17 reviews)
"Property was nice and clean"
United States
Luke S.
The price is CA $103
CA $256 total
includes taxes & fees
Mar 31 - Apr 1
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

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, (43 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 $137
CA $438 total
includes taxes & fees
Mar 29 - Mar 30
Comfortable cottage in gated community, 5 mins to OC and Assateague

OCHG VIRGINIA LEE

OCHG VIRGINIA LEE
2.0 star property
Downtown Ocean City
8.4 out of 10, Very good, (7 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 $272
CA $623 total
includes taxes & fees
Apr 1 - Apr 2
OCHG VIRGINIA LEE

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, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is CA $162
CA $395 total
includes taxes & fees
Mar 26 - Mar 27
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is CA $148
CA $386 total
includes taxes & fees
Mar 29 - Mar 30
Historic Chesapeake City Stay

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is CA $172
CA $440 total
includes taxes & fees
Apr 8 - Apr 9
Charming Coastal/Country Home w/3 Acres & Sauna!

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
9.6 out of 10, Exceptional, (20 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 $172 total
includes taxes & fees
Mar 26 - Mar 27
Guest Suite for up to 2 in a Victorian on the Chester River

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is CA $96
CA $153 total
includes taxes & fees
Mar 31 - Apr 1
Country Get Away Studio Apartment

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (52 reviews)
"Great little place "
United States
Eric R.
The price is CA $124
CA $273 total
includes taxes & fees
Apr 12 - Apr 13
Cottage near the Bay

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, (246 reviews)
"Great location and clean!"
United States
Susan V.
The price is CA $156
CA $312 total
includes taxes & fees
Mar 30 - Mar 31
Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very good, (6 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is CA $192
CA $439 total
includes taxes & fees
Mar 26 - Mar 27
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
North Ocean City
9.6 out of 10, Exceptional, (93 reviews)
"Views of both sunrise over the ocean and sunset over the bay, beautiful! Enjoyed the indoor pool, basketball court, game room, workout room and walks on the beach."
United States
Helen V.
The price is CA $133
CA $641 total
includes taxes & fees
Mar 30 - Mar 31
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway

Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway
North Ocean City
10.0 out of 10, Exceptional, (18 reviews)
"The condo is beautifully decorated and only steps from the beach! "
United States
Pamela H.
The price is CA $113
CA $325 total
includes taxes & fees
Mar 26 - Mar 27
Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach 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

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.