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, (1,305 reviews)
"Everything was great :) Great location...great staff!"
United States
Daria
The price is CA $129
CA $163 total
includes taxes & fees
May 11 - May 12
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 $127
CA $355 total
includes taxes & fees
May 10 - May 11
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
The price is CA $104
CA $358 total
includes taxes & fees
May 11 - May 12
Salisbury Riverfront Lofts

ELIS APARTMENT

ELIS APARTMENT
3.0 star property
Downtown Ocean City
9.2 out of 10, Wonderful, (5 reviews)
"Very nice place "
United States
Marvin R
The price is CA $157
CA $297 total
includes taxes & fees
Apr 30 - May 1
ELIS APARTMENT

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 $123
CA $280 total
includes taxes & fees
Apr 23 - Apr 24
Safari Apartments

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 $137
CA $219 total
includes taxes & fees
Apr 22 - Apr 23
First Floor Studio Apartment in Historic Chestertown

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 $171
CA $404 total
includes taxes & fees
Apr 13 - Apr 14
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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 $138
CA $441 total
includes taxes & fees
Apr 14 - Apr 15
Comfortable cottage in gated community, 5 mins to OC and Assateague

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 $149
CA $388 total
includes taxes & fees
Apr 19 - Apr 20
Historic Chesapeake City Stay

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (53 reviews)
"Great little place "
United States
Eric R.
The price is CA $112
CA $259 total
includes taxes & fees
Apr 13 - Apr 14
Cottage near the Bay

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, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is CA $88
CA $337 total
includes taxes & fees
Apr 12 - Apr 13
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 $94
CA $173 total
includes taxes & fees
Apr 14 - Apr 15
Guest Suite for up to 2 in a Victorian on the Chester River

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 $108
CA $330 total
includes taxes & fees
Apr 15 - Apr 16
On Main Street - Apartment C - Berlin, MD

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 $121
CA $375 total
includes taxes & fees
Apr 19 - Apr 20
Charming Coastal/Country Home w/3 Acres & Sauna!

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 $115
CA $271 total
includes taxes & fees
May 6 - May 7
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"This place is out in the country, but a short distance to lots of places we wanted to see, shop at, visit."
United States
Richard
The price is CA $97
CA $154 total
includes taxes & fees
Apr 22 - Apr 23
Country Get Away Studio Apartment

Ocean calling & country concert availability!

Ocean calling & country concert availability!
North Ocean City
9.0 out of 10, Wonderful, (35 reviews)
"We really enjoyed our stay here! Close to the beach and in walking distance of a lot of activities but also very quiet! Loved it!"
United States
Renee P.
The price is CA $87
CA $286 total
includes taxes & fees
Apr 14 - Apr 15
Ocean calling & country concert availability!

Wilmington Terrace

Wilmington Terrace
3.0 star property
Downtown Ocean City
8.4 out of 10, Very good, (10 reviews)
"Very clean and close to beach"
United States
Tony
The price is CA $132
CA $258 total
includes taxes & fees
Apr 30 - May 1
Wilmington Terrace

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
9.8 out of 10, Exceptional, (8 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is CA $166
CA $223 total
includes taxes & fees
Apr 14 - Apr 15
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

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 $215
CA $469 total
includes taxes & fees
Apr 15 - Apr 16
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
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.