Eastern Shore Vacation Homes

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

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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!

Stevensville

Michael V.

HK$2,235 total

includes taxes & fees

22 Oct - 23 Oct

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!

Stevensville

Anthony P.

HK$2,167 total

includes taxes & fees

21 Oct - 22 Oct

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

Cambridge

Mary Beth S.

HK$3,053 total

includes taxes & fees

19 Nov - 20 Nov

A dining area with a wooden table set for four, surrounded by wicker chairs.

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

North Ocean City

Rebecca D.

HK$2,369 total

includes taxes & fees

2 Nov - 3 Nov

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!

North Ocean City

Mike G.

HK$2,408 total

includes taxes & fees

2 Nov - 3 Nov

A building with a gabled roof and a circular vent on the roof.

6. BAYSIDE BUNGALOW

Rock Hall

Diane V.

HK$2,477 total

includes taxes & fees

21 Oct - 22 Oct

A dining area with a wooden table and chairs, a ceiling fan, and large windows with blinds.

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

North Ocean City

renee d.

HK$2,356 total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with white cabinetry, a stainless steel refrigerator, a microwave, and a dining area with white chairs and a wooden table.

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

Downtown Ocean City

Olivia R.

HK$2,408 total

includes taxes & fees

2 Nov - 3 Nov

9. Sands of Tide

North Ocean City

HK$3,797 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

10. Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Elkton

Shana G.

HK$3,026 total

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with wooden cabinets, a dining area set for six, and a large window providing natural light.

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

North Ocean City

Emma W.

HK$3,257 total

includes taxes & fees

30 Oct - 31 Oct

A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

12. Sunset Breezes - quiet waterfront retreat

Dorchester County

John C.

HK$2,522 total

includes taxes & fees

17 Nov - 18 Nov

A house surrounded by dense trees and a wooden dock extending into a body of water.

13. Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

Newark

David M.

HK$3,250 total

includes taxes & fees

3 Nov - 4 Nov

A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

14. Salisbury Cottage

Salisbury

Matthew B.

HK$2,862 total

includes taxes & fees

17 Nov - 18 Nov

A modern living room with a sofa, coffee table, dining table, and chairs. There is a TV mounted on the wall and artwork above the table.

15. BeachParadise107-OCEANVIEW Townhome-Steps to BEACH and BOARDWALK-LINENS INCLUDED

Downtown Ocean City

Anonymous traveller

HK$3,090 total

includes taxes & fees

21 Oct - 22 Oct

A spacious kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

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

Downtown Ocean City

Letizia

HK$2,400 total

includes taxes & fees

4 Nov - 5 Nov

A bedroom with a bed, a bedside table, a window with curtains, and a view of the sea.

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

Cambridge

HK$3,125 total

includes taxes & fees

21 Oct - 22 Oct

A bedroom with a bed, a ceiling fan, a door, and a view of the outdoors.

18. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...

Miriam G.

HK$2,238 total

includes taxes & fees

28 Oct - 29 Oct

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

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

Cambridge

Jill C.

HK$4,113 total

includes taxes & fees

21 Oct - 22 Oct

A single-story house with a front porch, a door, and a mailbox.

20. Salisbury Hideaway

Salisbury

Michelle S.

HK$2,845 total

includes taxes & fees

17 Nov - 18 Nov

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Top Eastern Shore Hotel Reviews

Fenwick Inn

10/10 Excellent

"It was great! Clean room. Staff was great!"

Plim Plaza Hotel

8/10 Good

"Hotel is old with small rooms. People are very nice and accommodating. Rooms are clean, however, not much countertop for makeup, hair products, jewelry and other necessities. We had a king size bed that was nice and comfortable but there was not room for a chair or any other option to sit other than on the bed. Nicely located on the boardwalk with places to eat in season. They supply coffee, but not in room, you have to go to the lobby to get it. Does have a nice size refrigerator and a microwave. Does not have a balcony. Nice front porch with rocking chairs. I could hear the person in the next room snoring, so the walls are a bit thin."

Grand Hotel Ocean City Oceanfront

8/10 Good

"We found our room to be surprisingly spacious, very clean, and comfortable; however, the kitchenette/bathroom areas were a bit dated. The property location was excellent and there were restaurants and a pool within the property. The common areas inside the hotel and the outdoor space at the front of the hotel were adequate, but guests were somewhat disrespectful, leaving their trash, not replacing chairs after their use, etc... The staff was pleasant enough when checking-in and helpful when we had a question but were ignoring simple tasks like straightening up the common areas when time allowed. Although this was a little off-putting, we would return if the opportunity presented itself."

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