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Our top choices for Eastern Shore vacation homes

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 357
AED 1,017 total
includes taxes & fees
8 Apr - 9 Apr
Charming Coastal/Country Home w/3 Acres & Sauna!

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 AED 298
AED 685 total
includes taxes & fees
12 Apr - 13 Apr
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 AED 396
AED 1,066 total
includes taxes & fees
5 Apr - 6 Apr
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 698
AED 1,503 total
includes taxes & fees
6 Apr - 7 Apr
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AED 735
AED 1,059 total
includes taxes & fees
30 Apr - 1 May
BAYSIDE BUNGALOW

Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches

Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches
Snow Hill
10.0 out of 10, Exceptional, (3 reviews)
"The hosts were wonderful, the house is beautiful, access & location was perfect. Next time I'm in the area & this place is avaliable, this is where I want to stay again. I recommend this house if you're in the area!!!Thanks to The Smiths"
United States
Sadat J.
The price is AED 479
AED 763 total
includes taxes & fees
12 Apr - 13 Apr
Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches

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 308
AED 607 total
includes taxes & fees
8 Apr - 9 Apr
Summer Rustic Camping with AC and King Bed

Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!
Smith Island
9.6 out of 10, Exceptional, (46 reviews)
"Very nice property! Spacious rooms, great host"
United States
Sara L.
The price is AED 658
AED 1,063 total
includes taxes & fees
5 Apr - 6 Apr
Historic home on Smith Island w/ dock!

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, (148 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is AED 949
AED 1,936 total
includes taxes & fees
6 Apr - 7 Apr
5-bedroom vacation home 5 minutes from historic Charlestown

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (36 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 503
AED 1,184 total
includes taxes & fees
14 Apr - 15 Apr
Salisbury Cottage

Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!

Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
Downtown Ocean City
10.0 out of 10, Exceptional, (21 reviews)
"Great vacation area and accommodation!"
United States
Letizia
The price is AED 275
AED 1,271 total
includes taxes & fees
2 Apr - 3 Apr
Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!

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)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AED 918
AED 1,538 total
includes taxes & fees
2 Apr - 3 Apr
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Come escape to Smith Island for the Spring and enjoy nature, peace and quiet

Come escape to Smith Island for the Spring and enjoy nature, peace and quiet
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 826
AED 1,322 total
includes taxes & fees
2 Apr - 3 Apr
Come escape to Smith Island for the Spring and enjoy nature, peace and quiet

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 643
AED 1,332 total
includes taxes & fees
21 Apr - 22 Apr
Bayside Cottage steps from Rock Hall Harbor

"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
North Ocean City
9.8 out of 10, Exceptional, (126 reviews)
"Exceeded all expectations, clean and well decorated. "
United States
Hannah R.
The price is AED 314
AED 1,318 total
includes taxes & fees
12 Apr - 13 Apr
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

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, (100 reviews)
"Property was perfect for us and our dogs."
United States
Jeffrey B.
The price is AED 551
AED 1,172 total
includes taxes & fees
1 May - 2 May
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!

BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!
North Ocean City
9.6 out of 10, Exceptional, (67 reviews)
"The place was beautiful , convenient to walk around to the beach and the stores "
United States
Theresa K.
The price is AED 248
AED 1,236 total
includes taxes & fees
2 Apr - 3 Apr
BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!

Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View

Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View
Downtown Ocean City
9.2 out of 10, Wonderful, (19 reviews)
"Really nice place,had everything we needed very elegant and relaxing,tvs nice and updated will come back again "
United States
George H.
The price is AED 275
AED 1,271 total
includes taxes & fees
12 Apr - 13 Apr
Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View

Beach Paradise III - DOWNTOWN OCEANVIEW Luxury Townhome-Steps to Beach&Boardwalk

Beach Paradise III - DOWNTOWN OCEANVIEW Luxury Townhome-Steps to Beach&Boardwalk
Downtown Ocean City
9.6 out of 10, Exceptional, (82 reviews)
"Beautiful Condo! Superb location! Extremely responsive communication with the owners! We’ll stay there again!"
United States
Amy b.
The price is AED 239
AED 1,222 total
includes taxes & fees
28 Apr - 29 Apr
Beach Paradise III - DOWNTOWN OCEANVIEW Luxury Townhome-Steps to Beach&Boardwalk

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 1,142
AED 2,269 total
includes taxes & fees
2 Apr - 3 Apr
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
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