Chesapeake Bay Vacation Rentals - HolidayHomes base64Hash Chesapeake Bay Vacation Rentals - HolidayHomes

Chesapeake Bay Vacation Rentals

Browse 10,384 available vacation homes and compared across 32 trusted partners

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Top-Rated Vacation rentals in Chesapeake Bay

Book the highest-rated Chesapeake Bay vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Elkton
Vacation home with patio & barbeque
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House Bohannon
Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!
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Cabin Port Republic
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
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House Deale
Family-friendly vacation home with garden, barbeque & patio
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Cabin Churchton
Chesapeake Bay Cottage
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House Northwest
Family-oriented vacation home with patio | Close to the beach | Good for workation
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House Madison
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
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House Buckroe Beach
Big, Beautiful & Beachside Bliss - Sleeps 10!
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House Fox Hill - Grandview
Waterfront Escape with Indoor Cedar Pool & Hot Tub-Chesapeake Bay Retreat
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House Northeast Virginia Beach
Beach Escape - 2 minute walk to the Beach!
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House Churchton
Vacation home with terrace & jacuzzi
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House Shady Side
Vacation home with garden, patio & barbeque | Nature view
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House Tracys Landing
Cute Bay Home/Fantastic View and Sandy Beach
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House Calvert Beach-Long Beach
Summer Getaway Beach Combing & Relaxation
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House Shady Side
Bay views with kayaks, bikes, fire pit, crabbing and more
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Top 15 most Recommended Vacation Rentals in Chesapeake Bay

Discover your ideal Chesapeake Bay vacation rental with real-time comparisons of 10,384 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Cape Charles
10 guests ∙ 4 bedrooms

House

Cape Charles, Northampton County, Virginia, United States
This house rental in Cape Charles accommodates 10 guests and features a family-friendly kitchen perfect for gatherings.
from $557
per night
(8)
View deal
Cabin Churchton
8 guests ∙ 3 bedrooms

Cabin

Churchton, Deale, Maryland, United States
This charming cabin in Churchton accommodates 8 guests and features a cozy fireplace for a perfect getaway.
from $218
per night
(92)
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House Northeast Virginia Beach
9 guests ∙ 4 bedrooms

House

Northeast Virginia Beach, Virginia Beach, Virginia, United States
This house rental in Northeast Virginia Beach accommodates 9 guests and features a family-friendly yard for outdoor enjoyment.
from $551
per night
(23)
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House Mathews
House ∙ 6 guests ∙ 4 bedrooms

260 m² House

Mathews, Westville, Virginia, United States
This house rental in Mathews accommodates 6 guests and features a cozy fireplace for warmth and comfort.
from $204
per night
(39)
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House Pasadena
House ∙ 14 guests ∙ 5 bedrooms

279 m² House

Pasadena, Anne Arundel County, Maryland, United States
Spacious house rental in Pasadena for 14 with a cozy fireplace and a family-friendly atmosphere.
from $498
per night
(99)
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House East Ocean View
House ∙ 10 guests ∙ 4 bedrooms

260 m² House

East Ocean View, Norfolk, Virginia, United States
This house rental in East Ocean View accommodates 10 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $204
per night
(80)
View deal
House Church Creek
House ∙ 40 guests ∙ 12 bedrooms

1045 m² House

Church Creek, Dorchester County, Maryland, United States
Spacious house rental in Church Creek accommodating 40 guests with a private pool and ample outdoor space for gatherings.
from $1,550
per night
(63)
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House Annapolis
9 guests ∙ 5 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
Spacious house rental in Annapolis accommodating 9 guests, featuring a cozy fireplace for warm gatherings.
from $230
per night
(4)
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House Bay View
House ∙ 12 guests ∙ 4 bedrooms

297 m² House

Bay View, Norfolk, Virginia, United States
This spacious house rental in Bay View accommodates 12 guests and features a balcony for relaxing views.
from $406
per night
(15)
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