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

Chesapeake Bay Vacation Rentals

Browse 10,062 available vacation homes and compared across 24 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 Virginia Beach
The Seahorse Beach Equestrian Property BEAUTIFUL & FRIENDLY HORSES ON SITE!
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House Cobbs Creek
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!
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House Reedville
Vacation home with patio, garden & heated pool
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House Northeast Virginia Beach
Vacation home with patio
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House Tracys Landing
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
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House Church Creek
House with private pool, yard & jacuzzi | Nature view
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Houseboat Havre de Grace
Children-friendly beautiful boat with terrace & BBQ | Pets are welcome
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Villa Earleville
Stunning waterfront villa with indoor pool and kids swing set and play area.
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House Cape Charles
Gorgeous New 5 BDR, 4 BA Beach Home With Tower Outlook Suite!
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House Willoughby Spit
Family-Friendly 5BR Beach Home • Dogs OK • Sleeps 10
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House Scotland
Chesapeake Bay Retreat – Private Beach • Fire Pit • WiFi • 2 Homes in 1
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House Parole
Vacation home with garden, private pool & terrace | Nature view
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House Kilmarnock
Spacious waterfront home with dock and sunset view
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House Northeast Virginia Beach
Beach Happy 4bdrm/9guests vacation gem steps to beach
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House Shady Side
Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
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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 10,062 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Northeast Virginia Beach
House ∙ 6 guests ∙ 3 bedrooms

House | Next to the beach

Northeast Virginia Beach, Virginia Beach, Virginia, United States
This house rental in Northeast Virginia Beach accommodates 6 guests and features a balcony for relaxing views.
from $381
per night
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House Broad Creek
House ∙ 8 guests ∙ 4 bedrooms

House with garden, sauna & barbecue | Suitable for remote work

Broad Creek, Norfolk, Virginia, United States
This house rental in Broad Creek accommodates 9 guests and features a family-friendly kitchen perfect for gatherings.
from $254
per night
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House Saint Michaels
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped vacation home with terrace, jacuzzi & private pool | Nature view | Pet-friendly

Saint Michaels, St. Michaels, Maryland, United States
This house rental in Saint Michaels accommodates 8 guests and features a private pool for relaxation and enjoyment.
from $620
per night
(4)
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House Northeast Virginia Beach
House ∙ 9 guests ∙ 3 bedrooms

House with private pool

Northeast Virginia Beach, Virginia Beach, Virginia, United States
This house rental in Northeast Virginia Beach accommodates 9 guests and features a private pool for family-friendly enjoyment.
from $633
per night
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House Norfolk
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with barbecue

Norfolk, Virginia, United States
This spacious house rental in Norfolk accommodates 10 guests and features a cozy fireplace for a comfortable stay.
from $363
per night
(6)
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House Cape Charles
House ∙ 9 guests ∙ 3 bedrooms

Children-friendly vacation home with garden, pool & barbecue | Perfect for remote work | Pets are welcome

Cape Charles, Northampton County, Virginia, United States
This house rental in Cape Charles accommodates 9 guests and features a family-friendly kitchen for enjoyable gatherings.
from $291
per night
(33)
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House Bay View
House ∙ 9 guests ∙ 4 bedrooms

Family-friendly pleasant vacation home with terrace, barbecue & yard | Pets allowed

Bay View, Norfolk, Virginia, United States
This house rental in Bay View accommodates 9 guests and features a spacious yard for outdoor enjoyment.
from $229
per night
(34)
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House Willoughby Spit
House ∙ 10 guests ∙ 4 bedrooms

House with 4 bedrooms for 10 persons

Willoughby Spit, Norfolk, Virginia, United States
This house rental in Willoughby Spit accommodates 11 guests and allows pets for a comfortable stay.
from $430
per night
(23)
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House Buckroe Beach
House ∙ 4 guests ∙ 2 bedrooms

House with 2 bedrooms for 4 persons

Buckroe Beach, Hampton, Virginia, United States
This house rental in Buckroe Beach accommodates 4 guests and features a fully equipped kitchen for your convenience.
from $189
per night
(2)
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