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Our top choices for Eastern Shore vacation homes

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 AED 298
AED 685 total
includes taxes & fees
18 May - 19 May
Cottage near the Bay

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 AED 551
AED 1,177 total
includes taxes & fees
17 May - 18 May
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (54 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AED 735
AED 1,114 total
includes taxes & fees
18 May - 19 May
BAYSIDE BUNGALOW

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 AED 637
AED 1,368 total
includes taxes & fees
1 Jun - 2 Jun
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is AED 826
AED 1,670 total
includes taxes & fees
26 May - 27 May
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (38 reviews)
"My family and I had a great stay was a comfy and safe space to relax and enjoy our Halloween weekend would definitely recommend!"
United States
Mackenzie N.
The price is AED 628
AED 1,382 total
includes taxes & fees
18 May - 19 May
Salisbury Cottage

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.8 out of 10, Exceptional, (6 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 AED 367
AED 666 total
includes taxes & fees
10 Jun - 11 Jun
Summer Rustic Camping with AC and King Bed

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 AED 677
AED 1,410 total
includes taxes & fees
27 May - 28 May
Charming Coastal/Country Home w/3 Acres & Sauna!

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 AED 496
AED 1,238 total
includes taxes & fees
14 May - 15 May
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Summer is almost here on Smith Island! Get ready for a great season on the Bay

Summer is almost here on Smith Island! Get ready for a great season on the Bay
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Excellent property, excellent host. This is a very well-appointed property located very close to the ferry dock. Golf cart, bikes, and kayaks were in great shape. Chris could not have been a more responsive or helpful host."
United States
Timothy S.
The price is AED 643
AED 1,075 total
includes taxes & fees
31 May - 1 Jun
Summer is almost here on Smith Island! Get ready for a great season on the Bay

Tranquil Direct Waterfront house in West Ocean City, MD!!!!

Tranquil Direct Waterfront house in West Ocean City, MD!!!!
West Ocean City
10.0 out of 10, Exceptional, (1 review)
"Had a fantastic stay here. The neighborhood was quiet and peaceful, beautiful view of the water and an awesome place to catch a sunset. The host was absolutely amazing — friendly, personable, and quick to respond. Location was convenient and close to pretty much everything we wanted to do. Check-in and check-out were very easy. The house was a perfect size for us (2 adults and our dog), well maintained and very clean. Would definitely stay here again."
United States
Christine G.
The price is AED 1,098
AED 2,464 total
includes taxes & fees
1 Jun - 2 Jun
Tranquil Direct Waterfront house in West Ocean City, MD!!!!

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Great overnight stay for a wedding nearby. Would highly recommend!"
United States
Kevin F.
The price is AED 918
AED 1,538 total
includes taxes & fees
18 May - 19 May
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is AED 742
AED 1,448 total
includes taxes & fees
2 Jun - 3 Jun
Bayside Cottage steps from Rock Hall Harbor

Beach Happy Apartment 7 Elis Apartment

Beach Happy Apartment 7 Elis Apartment
Downtown Ocean City
8.8 out of 10, Excellent, (10 reviews)
"Exactly what I was looking for. "
United States
Conor B.
The price is AED 400
AED 901 total
includes taxes & fees
14 May - 15 May
Beach Happy Apartment 7 Elis Apartment

Ideal for a family getaway, newly furnished home in Montego Bay waiting for you!

Ideal for a family getaway, newly furnished home in Montego Bay waiting for you!
North Ocean City
10.0 out of 10, Exceptional, (27 reviews)
"Our 3rd time staying here, best place that is dog friendly in OCMD!"
United States
brian d.
Ideal for a family getaway, newly furnished home in Montego Bay waiting for you!

Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (21 reviews)
"Had a wonderful time house had everything you would need for a stay located right in the heart of Salisbury. Will definitely be going back to stay in this particular house. Thank you"
United States
Bryan M.
The price is AED 547
AED 1,281 total
includes taxes & fees
28 May - 29 May
Salisbury Hideaway

Spacious, recently renovated centrally located condo with pool and parking

Spacious, recently renovated centrally located condo with pool and parking
Downtown Ocean City
10.0 out of 10, Exceptional, (4 reviews)
"Great condo and location!"
United States
Emily D.
The price is AED 691
AED 1,580 total
includes taxes & fees
15 May - 16 May
Spacious, recently renovated centrally located condo with pool and parking

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (12 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is AED 1,322
AED 2,239 total
includes taxes & fees
18 May - 19 May
Turnbridge Manor

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
8.8 out of 10, Excellent, (10 reviews)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
The price is AED 1,295
AED 2,455 total
includes taxes & fees
21 May - 22 May
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (151 reviews)
"This is the second time my group of friends has stayed here. The house is very comfortable and well-appointed, and the view is gorgeous! "
United States
Melinda S.
The price is AED 1,015
AED 2,002 total
includes taxes & fees
19 May - 20 May
5-bedroom vacation home 5 minutes from historic Charlestown
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