Eastern Shore Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Eastern Shore vacation rentals

Exterior

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 ￥14,896
￥18,813 total
includes taxes & fees
May 18 - May 19
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
Exterior

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 ￥15,413
￥21,232 total
includes taxes & fees
May 27 - May 28
Majestic Hotel & Apartments
Apartment D: Riverfront Grand | 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 ￥10,646
￥39,640 total
includes taxes & fees
May 18 - May 19
Salisbury Riverfront Lofts
Family Apartment | 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 ￥16,504
￥38,709 total
includes taxes & fees
May 20 - May 21
ELIS APARTMENT
House (3 Bedrooms) | 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 ￥16,509
￥42,958 total
includes taxes & fees
May 18 - May 19
6 Mi to Salisbury: Forest-view Sanctuary!
Beach nearby

On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.2 out of 10, Wonderful, (30 reviews)
"We loved everything about our stay! This place is adorable and the location is awesome!"
United States
kelly K.
The price is ￥13,969
￥39,414 total
includes taxes & fees
May 18 - May 19
On Main Street - Apartment C - Berlin, MD
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful place and host, very peaceful and quiet with plenty of nature !!!"
United States
Daniel V.
The price is ￥11,112
￥17,668 total
includes taxes & fees
May 25 - May 26
Country Get Away Studio Apartment
Terrace/patio

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 ￥15,537
￥33,704 total
includes taxes & fees
May 20 - May 21
Safari Apartments
Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (21 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is ￥17,105
￥44,153 total
includes taxes & fees
May 20 - May 21
Historic Chesapeake City Stay
Interior

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, (19 reviews)
"Property was nice and clean"
United States
Luke S.
The price is ￥19,684
￥38,111 total
includes taxes & fees
May 22 - May 23
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
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, (21 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is ￥18,700
￥44,683 total
includes taxes & fees
May 18 - May 19
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV

Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N

Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
North Ocean City
9.0 out of 10, Wonderful, (37 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 ￥9,978
￥32,462 total
includes taxes & fees
May 28 - May 29
Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
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, (21 reviews)
"Good place, clean and a good location."
United States
Bernard S.
The price is ￥10,770
￥19,810 total
includes taxes & fees
May 28 - May 29
Guest Suite for up to 2 in a Victorian on the Chester River
Interior

Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!

Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!
Midtown Ocean City
9.8 out of 10, Exceptional, (7 reviews)
"beautiful place quiet,close to all amenities,clean and great host."
Canada
Tom S.
The price is ￥23,757
￥54,457 total
includes taxes & fees
Jun 1 - Jun 2
Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!
Outdoor pool

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, (46 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 ￥21,381
￥57,295 total
includes taxes & fees
May 17 - May 18
Comfortable cottage in gated community, 5 mins to OC and Assateague
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, (44 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 ￥27,511
￥59,618 total
includes taxes & fees
Jun 3 - Jun 4
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Property grounds

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 ￥15,680
￥25,157 total
includes taxes & fees
May 28 - May 29
First Floor Studio Apartment in Historic Chestertown
Interior

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (54 reviews)
"Property was exactly as pictured, Crystal is very prompt if contacted & very accomdating to questions. If you are looking in ng for some quiet peacefulness yet close to the water, or nearby towns & attractions & travel with your dog this is the perfect spot! My dogs were very content & I had no worries as to if they would be bothered by distractions because there are no distractions, it was a vacation for them as well as cottage is on a quiet street & it was very nice to sit outside wuth them &...
United States
Shelley
The price is ￥12,858
￥29,615 total
includes taxes & fees
May 17 - May 18
Cottage near the Bay
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, (102 reviews)
"Property was perfect for us and our dogs."
United States
Jeffrey B.
The price is ￥23,757
￥50,200 total
includes taxes & fees
May 21 - May 22
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Smart TV

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, (10 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is ￥19,006
￥25,519 total
includes taxes & fees
May 17 - May 18
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
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

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

8/10 Good
"Nice view of the boardwalk and ocean. "
James 1-night trip
Posted 2 hours ago
Grand Hotel Ocean City Oceanfront

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