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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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 stay"
United States
Michael V.
The price is €678
includes taxes & fees
30 Oct - 31 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, (56 reviews)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
The price is €236
includes taxes & fees
19 Oct - 20 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, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
The price is €348
includes taxes & fees
17 Nov - 18 Nov
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A waterfront property with multiple-story buildings, a dock with boats, and a wooden pier.

4. 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, (162 reviews)
"Great house, location was excellent "
United States
Mike G.
The price is €264
includes taxes & fees
1 Nov - 2 Nov
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
A building with a gabled roof and a circular vent on the roof.

5. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is €285
includes taxes & fees
20 Oct - 21 Oct
BAYSIDE BUNGALOW
A modern kitchen with white cabinetry, a stainless steel refrigerator, a microwave, and a dining area with white chairs and a wooden table.

6. 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
9.6 out of 10, Exceptional, (31 reviews)
"Great space, close to the beach, we had an amazing stay!"
United States
Olivia R.
Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View
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

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 €263
includes taxes & fees
1 Nov - 2 Nov
Beach Paradise 105 - Beach Home at Broad Marsh OC
A bunk bed room with white bedding and blue throw blankets.

8. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is €343
includes taxes & fees
19 Oct - 20 Oct
Bohemia Manor Farm
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

9. 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 €455
includes taxes & fees
19 Oct - 20 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

10. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (63 reviews)
"Nice cottage at the end of a quiet lane, priced reasonably. Host is very accommodating. We had a lovely stay and enjoyed our time in Crisfield."
United States
Karen J.
The price is €170
includes taxes & fees
18 Oct - 19 Oct
Cottage near the Bay
A bedroom with a bed, dresser, and a door.

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

More, than just a place to sleep - welcome home!
Cambridge
The price is €360
includes taxes & fees
26 Oct - 27 Oct
More, than just a place to sleep - welcome home!
A single-story house with a front porch, a door, and a mailbox.

12. 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 €330
includes taxes & fees
3 Nov - 4 Nov
Salisbury Hideaway
A sandy beach with footprints, a pier in the distance, and a clear sky.

13. 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 €224
includes taxes & fees
24 Oct - 25 Oct
Tangier Escape, great place get away from it all on Deal Island, MD.
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.

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

BeachParadise107-OCEANVIEW Townhome-Steps to BEACH and BOARDWALK-LINENS INCLUDED
Downtown Ocean City
10.0 out of 10, Exceptional, (5 reviews)
"The house was as listed, it was an enjoyable stay. Ann was easy to work with. Thanks VRBO."
United States
Anonymous traveller
The price is €335
includes taxes & fees
20 Oct - 21 Oct
BeachParadise107-OCEANVIEW Townhome-Steps to BEACH and BOARDWALK-LINENS INCLUDED
A house with a large lawn and a dock extending into a calm lake.

15. 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 €270
includes taxes & fees
19 Oct - 20 Oct
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
A wooden interior with a dining area, sofas, and a table.

16. 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
9.0 out of 10, Wonderful, (15 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveller
The price is €509
includes taxes & fees
18 Oct - 19 Oct
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A spacious kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

17. 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, (36 reviews)
"Great vacation area and accommodation!"
United States
Letizia
The price is €266
includes taxes & fees
15 Nov - 16 Nov
Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
A house with a covered porch, a grill, and a propane tank in the yard.

18. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is €309
includes taxes & fees
20 Oct - 21 Oct
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

19. 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 €336
includes taxes & fees
19 Oct - 20 Oct
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
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

10/10 Excellent
"Very nice"
James 4-night trip
Posted less than an hour ago
Days Inn by Wyndham Ocean City Oceanfront

Find out more about Eastern Shore

Eastern Shore Holiday Homes information

Number of reviews
507
Accommodation
569 Holiday Homes
Lowest Price
€170
Highest Price
€678

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