A marina with numerous boats docked at wooden piers under a clear sky.

Eastern Shore Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Eastern Shore holiday rentals

Terrace/patio

Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
6.0 out of 10, (382 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 HK$882
HK$1,027 total
includes taxes & fees
9 Jul - 10 Jul
Majestic Hotel & Apartments
Terrace/patio

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 HK$1,101
HK$2,232 total
includes taxes & fees
1 Jul - 2 Jul
ELIS APARTMENT
2 bedrooms, individually decorated, individually furnished

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 HK$604
HK$2,045 total
includes taxes & fees
1 Jul - 2 Jul
Salisbury Riverfront Lofts
Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (23 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is HK$847
HK$2,186 total
includes taxes & fees
1 Jul - 2 Jul
Historic Chesapeake City Stay
Interior

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 HK$635
HK$1,463 total
includes taxes & fees
1 Jul - 2 Jul
Cottage near the Bay
Exterior

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 HK$549
HK$873 total
includes taxes & fees
7 Jul - 8 Jul
Country Get Away Studio Apartment
Beach

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, (24 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is HK$924
HK$2,224 total
includes taxes & fees
1 Jul - 2 Jul
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Exterior

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 HK$533
HK$981 total
includes taxes & fees
6 Jul - 7 Jul
Guest Suite for up to 2 in a Victorian on the Chester River
2 bedrooms, desk, iron/ironing board, travel cot

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, (21 reviews)
"Property was nice and clean"
United States
Luke S.
The price is HK$659
HK$1,540 total
includes taxes & fees
1 Jul - 2 Jul
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (115 reviews)
"Every thing was great"
United States
lesia k.
The price is HK$776
HK$1,245 total
includes taxes & fees
6 Jul - 7 Jul
First Floor Studio Apartment in Historic Chestertown
Exterior

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, (47 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 HK$761
HK$2,166 total
includes taxes & fees
1 Jul - 2 Jul
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is HK$726
HK$2,153 total
includes taxes & fees
2 Jul - 3 Jul
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

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, (1,309 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 HK$1,374
HK$1,539 total
includes taxes & fees
6 Jul - 7 Jul
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
Front of property

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is HK$1,035
HK$2,126 total
includes taxes & fees
1 Jul - 2 Jul
6 Mi to Salisbury: Forest-view Sanctuary!
Fridge, microwave, oven, stovetop

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 HK$1,059
HK$2,676 total
includes taxes & fees
13 Jul - 14 Jul
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Beach nearby

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 HK$1,231
HK$2,678 total
includes taxes & fees
16 Jul - 17 Jul
On Main Street - Apartment C - Berlin, MD
Outdoor dining

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 HK$1,176
HK$2,512 total
includes taxes & fees
7 Jul - 8 Jul
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Exterior

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 HK$941
HK$1,263 total
includes taxes & fees
1 Jul - 2 Jul
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
1 bedroom

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.8 out of 10, Exceptional, (7 reviews)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
United States
Rees L.
The price is HK$803
HK$1,464 total
includes taxes & fees
8 Jul - 9 Jul
Summer Rustic Camping with AC and King Bed
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (56 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is HK$1,568
HK$2,352 total
includes taxes & fees
1 Jul - 2 Jul
BAYSIDE BUNGALOW
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

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

10/10 Excellent
"Wonderful location!"
Monique 3-night trip
Posted 1 hour ago
Holiday Inn & Suites Ocean City by IHG

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