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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Eastern Shore holiday homes

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

1. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is HK$747
HK$2,334 total
includes taxes & fees
5 Oct - 6 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A building with a gabled roof and a circular vent on the roof.

2. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (66 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is HK$1,569
HK$2,477 total
includes taxes & fees
4 Oct - 5 Oct
BAYSIDE BUNGALOW
A lighthouse with a white exterior, a balcony, and a metal roof.

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is HK$694
HK$2,243 total
includes taxes & fees
4 Oct - 5 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

4. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is HK$1,255
HK$2,936 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A bunk bed room with white bedding and blue throw blankets.

5. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is HK$2,854
HK$3,025 total
includes taxes & fees
13 Oct - 14 Oct
Bohemia Manor Farm
A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

6. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (63 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
The price is HK$636
HK$1,464 total
includes taxes & fees
12 Oct - 13 Oct
Cottage near the Bay
A bedroom with a bed, a dresser, a mirror, and a window with curtains.

7. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!
Cambridge
The price is HK$2,330
HK$3,133 total
includes taxes & fees
2 Oct - 3 Oct
More, than just a place to sleep - welcome home!
A kitchen with wooden cabinets, a dining table, and a refrigerator.

8. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
Family Retreat at Lansdowne Manor
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

9. 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, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

10. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (67 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is HK$1,805
HK$2,154 total
includes taxes & fees
25 Oct - 26 Oct
Waterfront Getaway with Dock
A dining area with a wooden table set for four, surrounded by wicker chairs.

11. "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
9.6 out of 10, Exceptional, (140 reviews)
"Great place to stay. There was plenty of room, easy access to close shopping."
United States
Rebecca D.
The price is HK$596
HK$2,689 total
includes taxes & fees
4 Oct - 5 Oct
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
A wooden gazebo with a table and chairs, surrounded by plants and a grill.

12. 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, (112 reviews)
"Great hosting by Laurie"
United States
Jim C.
The price is HK$1,569
HK$3,014 total
includes taxes & fees
4 Oct - 5 Oct
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Exterior

13. Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
10.0 out of 10, Exceptional, (3 reviews)
"Renee & Pat were excellent hosts and we will definitely try to book again when in the area. Everything was as advertised and much more. Being pet friendly was a plus. We enjoyed two restaurants in the area while there, Lee's Landing and Old South Smokehouse, highly recommend!"
United States
Don S.
The price is HK$1,342
HK$1,525 total
includes taxes & fees
2 Oct - 3 Oct
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A dining area with a wooden table and chairs, a ceiling fan, and large windows with blinds.

14. Beach Paradise 105 - Beach Home at Broad Marsh OC

Beach Paradise 105 - Beach Home at Broad Marsh OC
North Ocean City
9.8 out of 10, Exceptional, (13 reviews)
"Loved this property. It was clean and had everything we needed. Had a wonderful stay!! Highly recommend!"
United States
renee d.
The price is HK$432
HK$2,496 total
includes taxes & fees
26 Oct - 27 Oct
Beach Paradise 105 - Beach Home at Broad Marsh OC
A modern kitchen with wooden cabinets, a dining area set for six, and a large window providing natural light.

15. 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, (80 reviews)
"Very nice stay"
United States
Emma W.
The price is HK$1,530
HK$3,902 total
includes taxes & fees
30 Oct - 31 Oct
BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!
A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

16. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
Bayside Cottage steps from Rock Hall Harbor
A kitchen with a farmhouse sign, a clock, and a refrigerator.

17. Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (23 reviews)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
United States
Ryan B.
Cozy Barn Loft: Country Views & Central to Beaches
A waterfront property with multiple-story buildings, a dock with boats, and a wooden pier.

18. BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
North Ocean City
9.8 out of 10, Exceptional, (159 reviews)
"Great house, location was excellent "
United States
Mike G.
The price is HK$353
HK$2,311 total
includes taxes & fees
1 Nov - 2 Nov
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
A single-story house with a front porch, a door, and a mailbox.

19. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (24 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is HK$1,114
HK$2,770 total
includes taxes & fees
5 Oct - 6 Oct
Salisbury Hideaway
A sandy beach with footprints, a pier in the distance, and a clear sky.

20. Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is HK$863
HK$1,930 total
includes taxes & fees
8 Oct - 9 Oct
Tangier Escape, great place get away from it all on Deal Island, MD.
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

Dunes Suites Oceanfront

Dunes Suites Oceanfront

10/10 Excellent
"I thought the room was very clean. The staff was very helpful."
Wilma 4-night trip
Posted 8 hours ago
Dunes Suites Oceanfront

Find out more about Eastern Shore

Eastern Shore Vacation Homes information

Number of reviews
751
Accommodation
453 Vacation Homes
Lowest Price
HK$1,464
Highest Price
HK$3,902

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