Eastern Shore Vacation Rentals

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Our top choices for Eastern Shore vacation rentals

Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
6.0 out of 10, (370 reviews)
"Amazing location and staff was very nice! It felt super safe. As a female solo traveler, felt super safe here!"
United States
Mia
The price is CA $139
CA $163 total
includes taxes & fees
Jun 24 - Jun 25
Majestic Hotel & Apartments

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (22 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is CA $153
CA $396 total
includes taxes & fees
Jun 25 - Jun 26
Historic Chesapeake City Stay

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, (23 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is CA $167
CA $406 total
includes taxes & fees
Jun 24 - Jun 25
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (42 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is CA $99
CA $158 total
includes taxes & fees
Jul 6 - Jul 7
Country Get Away Studio Apartment

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (56 reviews)
"Cottage was exactly as listed. Great value"
United States
Tom B.
The price is CA $115
CA $266 total
includes taxes & fees
Jun 24 - Jun 25
Cottage near the Bay

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (113 reviews)
"Every thing was great"
United States
lesia k.
The price is CA $140
CA $225 total
includes taxes & fees
Jul 6 - Jul 7
First Floor Studio Apartment in Historic Chestertown

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
10.0 out of 10, Exceptional, (3 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is CA $192
CA $486 total
includes taxes & fees
Jul 7 - Jul 8
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

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, (20 reviews)
"Property was nice and clean"
United States
Luke S.
The price is CA $163
CA $335 total
includes taxes & fees
Jun 29 - Jun 30
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.2 out of 10, Wonderful, (25 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is CA $149
CA $414 total
includes taxes & fees
Jun 29 - Jun 30
Salisbury Riverfront Lofts

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, (23 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 $96
CA $177 total
includes taxes & fees
Jun 29 - Jun 30
Guest Suite for up to 2 in a Victorian on the Chester River

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, (46 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is CA $184
CA $469 total
includes taxes & fees
Jun 30 - Jul 1
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is CA $147
CA $383 total
includes taxes & fees
Jun 25 - Jun 26
6 Mi to Salisbury: Forest-view Sanctuary!

On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (35 reviews)
"We loved everything about our stay! This place is adorable and the location is awesome!"
United States
kelly K.
The price is CA $191
CA $444 total
includes taxes & fees
Jul 5 - Jul 6
On Main Street - Apartment C - Berlin, MD

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Berlin
9.8 out of 10, Exceptional, (105 reviews)
"This property and its owner were everything we look for in a vacation rental. Listing is as an old farm house does not do it justice. The owner has carefully curated it it with an electric collection of furniture ,pottery and various hand crafted items. She has put her heart and soul into this house and you can feel.it ad soon as you step inside. We will definitely be back.😍😍😍😍😍 The McCartney's and the Horneffs.......Thanks again for everything Laurie."
United States
Melinda
The price is CA $318
CA $590 total
includes taxes & fees
Jun 29 - Jun 30
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

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
10.0 out of 10, Exceptional, (12 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is CA $170
CA $228 total
includes taxes & fees
Jun 24 - Jun 25
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

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, (1,308 reviews)
"The room had issues in the toilet and also the ceiling broke and ended up ruining a pair of shoes from a leakage. The description of the pictures was not accurate to the room. I was supposed to have a suite and had one regular room with balcony."
United States
Eivy
The price is CA $259
CA $290 total
includes taxes & fees
Jul 6 - Jul 7
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

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 $172
CA $373 total
includes taxes & fees
Jun 30 - Jul 1
ELIS APARTMENT

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
9.8 out of 10, Exceptional, (45 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is CA $248
CA $299 total
includes taxes & fees
Jun 25 - Jun 26
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
7.8 out of 10, Good, (7 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is CA $290
CA $566 total
includes taxes & fees
Jul 20 - Jul 21
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (33 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is CA $219
CA $359 total
includes taxes & fees
Jun 25 - Jun 26
Sailwinds Loft at Cambridge Creek
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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