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

Holiday Homes in Eastern Shore

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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 lighthouse with a white exterior, a balcony, and a metal roof.

1. 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 NZ$489
includes taxes & fees
4 Oct - 5 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

2. 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 NZ$505
includes taxes & fees
5 Oct - 6 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

3. 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 NZ$664
includes taxes & fees
27 Oct - 28 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A building with a gabled roof and a circular vent on the roof.

4. 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 NZ$545
includes taxes & fees
4 Oct - 5 Oct
BAYSIDE BUNGALOW
A waterfront property with multiple-story buildings, a dock with boats, and a wooden pier.

5. 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 NZ$537
includes taxes & fees
1 Nov - 2 Nov
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
A bunk bed room with white bedding and blue throw blankets.

6. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is NZ$592
includes taxes & fees
19 Oct - 20 Oct
Bohemia Manor Farm
A dining area with a wooden table set for four, surrounded by wicker chairs.

7. "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 NZ$598
includes taxes & fees
4 Oct - 5 Oct
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
A single-story house with a front porch, a door, and a mailbox.

8. 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 NZ$562
includes taxes & fees
4 Oct - 5 Oct
Salisbury Hideaway
A modern kitchen with white cabinetry, a stainless steel refrigerator, a microwave, and a dining area with white chairs and a wooden table.

9. 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
9.4 out of 10, Exceptional, (30 reviews)
"Great space, close to the beach, we had an amazing stay!"
United States
Olivia R.
The price is NZ$537
includes taxes & fees
1 Nov - 2 Nov
Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

10. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"Super convenient to campus and everything was clean and worked perfectly. Overall, a great stay and met all of our expectations."
United States
Matthew B.
The price is NZ$617
includes taxes & fees
19 Oct - 20 Oct
Salisbury Cottage
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

11. 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
9.8 out of 10, Exceptional, (6 reviews)
"Nothing fancy but extremely functional! House was clean, had what we needed in kitchen, beds were comfy. Would highly recommend!"
United States
Shana G.
The price is NZ$652
includes taxes & fees
13 Oct - 14 Oct
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A dining area with a wooden table and chairs, a ceiling fan, and large windows with blinds.

12. 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 NZ$568
includes taxes & fees
29 Oct - 30 Oct
Beach Paradise 105 - Beach Home at Broad Marsh OC
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

13. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is NZ$1,033
includes taxes & fees
27 Oct - 28 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A sandy beach with footprints, a pier in the distance, and a clear sky.

14. 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 NZ$438
includes taxes & fees
10 Oct - 11 Oct
Tangier Escape, great place get away from it all on Deal Island, MD.
A wooden gazebo with a table and chairs, surrounded by plants and a grill.

15. 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 NZ$676
includes taxes & fees
4 Oct - 5 Oct
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

16. 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 NZ$483
includes taxes & fees
19 Oct - 20 Oct
Waterfront Getaway with Dock
Outdoor dining

17. 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 NZ$344
includes taxes & fees
12 Oct - 13 Oct
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A house with a large lawn and a dock extending into a calm lake.

18. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is NZ$529
includes taxes & fees
5 Oct - 6 Oct
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
A modern living room with a sofa, coffee table, dining table, and chairs. There is a TV mounted on the wall and artwork displayed above the table.

19. 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
9.8 out of 10, Exceptional, (96 reviews)
"Beautiful home, great area. "
United States
Cleotrina S.
The price is NZ$567
includes taxes & fees
20 Oct - 21 Oct
Beach Paradise III - DOWNTOWN OCEANVIEW Luxury Townhome-Steps to Beach&Boardwalk
A spacious living area with a large window, a ceiling fan, and a dining area with a view of the outdoors.

20. Spacious canal-front home with private dock, parking, and family-friendly amenities.

Spacious canal-front home with private dock, parking, and family-friendly amenities.
Ocean Pines
10.0 out of 10, Exceptional, (2 reviews)
"The home was beautiful, very clean and spacious. The back deck had a beautiful view of the canal and was very peaceful. Check in and out process was very easy. Owner was very communicative before, during and after our stay answering any questions I had. Location was perfect, just about 10 minutes from Ocean City, close to the beach and boardwalk. We very much enjoyed our stay here and would definitely return !"
United States
Alyssa L.
The price is NZ$1,799
includes taxes & fees
28 Oct - 29 Oct
Spacious canal-front home with private dock, parking, and family-friendly amenities.
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

Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

8/10 Good
"room was clean and comfortable. The only concern was no hot water or soap in the shower dispenser"
George 2-night trip
Posted 22 hours ago
Days Inn by Wyndham Ocean City Oceanfront

Find out more about Eastern Shore

Eastern Shore Holiday Homes information

Number of reviews
849
Accommodation
476 Holiday Homes
Lowest Price
NZ$344
Highest Price
NZ$1,799

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