Chesapeake Bay Vacation Rentals - Wimdu base64Hash Chesapeake Bay Vacation Rentals - Wimdu

Chesapeake Bay Vacation Rentals

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Choose from 12,415 vacation rentals and homes for your trip!

Best-rated vacation rentals in Chesapeake Bay

Discover vacation rentals with top-notch guest ratings

House Buckroe Beach
from $230 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding(129 ratings)
Buckroe Beach, Hampton, Virginia, United States
Vrbo
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House Cape Charles
from $565 per night
House ∙ 16 guests ∙ 6 bedrooms
4.9
Outstanding(32 ratings)
Cape Charles, Northampton County, Virginia, United States
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House West Ocean View
from $288 per night
House ∙ 16 guests ∙ 7 bedrooms
4.6
Excellent(23 ratings)
West Ocean View, Norfolk, Virginia, United States
Vrbo
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Pet-friendly rentals in Chesapeake Bay

Explore best dog-friendly accommodation offers and enjoy vacation with your pet

House Virginia Beach
from $106 per night
House ∙ 4 guests ∙ 2 bedrooms
Virginia Beach, Virginia, United States
Pet-friendly
Vrbo
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House Churchton
from $573 per night
House ∙ 13 guests ∙ 7 bedrooms
4.6
Excellent(18 ratings)
Churchton, Deale, Maryland, United States
Pet-friendly
Vrbo
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House Cape Saint Claire
from $759 per night
House ∙ 18 guests ∙ 6 bedrooms
5.0
Outstanding(41 ratings)
Cape Saint Claire, Anne Arundel County, Maryland, United States
Pet-friendly
Vrbo
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Vacation rentals with pool in Chesapeake Bay

Discover best cabin and house rentals with pool in Chesapeake Bay

House Cambridge
from $896 per night
House ∙ 16 guests ∙ 5 bedrooms
4.8
Outstanding(29 ratings)
Cambridge, Dorchester County, Maryland, United States
Pool
Vrbo
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House Cape Charles
from $527 per night
House ∙ 11 guests ∙ 4 bedrooms
4.9
Outstanding(55 ratings)
Cape Charles, Northampton County, Virginia, United States
Pool
Vrbo
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House Rock Hall
from $897 per night
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding(80 ratings)
Rock Hall, Edesville, Maryland, United States
Pool
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Best vacation rental offers in Chesapeake Bay

House Cape Charles
from $356 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(81 ratings)
Cape Charles, Northampton County, Virginia, United States
Vrbo
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Cottage Lusby
from $77 per night
Cottage ∙ 3 guests ∙ 1 bedroom
5.0
Outstanding(26 ratings)
Lusby, Solomons Island, Maryland, United States
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House Parole
from $394 per night
House ∙ 12 guests ∙ 8 bedrooms
5.0
Outstanding(1 rating)
Parole, Anne Arundel County, Maryland, United States
Vrbo
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Condo Northeast Virginia Beach
from $789 per night
Condo ∙ 15 guests ∙ 7 bedrooms
5.0
Outstanding(47 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
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House Annapolis
from $634 per night
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding(45 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Vrbo
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House Willoughby Spit
from $267 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent(164 ratings)
Willoughby Spit, Norfolk, Virginia, United States
Vrbo
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House Madison
from $988 per night
House ∙ 24 guests ∙ 10 bedrooms
5.0
Outstanding(72 ratings)
Madison, Dorchester County, Maryland, United States
Vrbo
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House Tilghman
from $474 per night
House ∙ 8 guests ∙ 5 bedrooms
5.0
Outstanding(34 ratings)
Tilghman, Tilghman Island, Maryland, United States
Vrbo
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House Chesapeake
from $252 per night
House ∙ 11 guests ∙ 6 bedrooms
5.0
Outstanding(15 ratings)
Chesapeake, Virginia, United States
Vrbo
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House Cape Charles
from $399 per night
House ∙ 13 guests ∙ 5 bedrooms
5.0
Outstanding(9 ratings)
Cape Charles, Northampton County, Virginia, United States
Vrbo
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House Chic's Beach
from $302 per night
House ∙ 10 guests ∙ 4 bedrooms
4.9
Outstanding(45 ratings)
Chic's Beach, Virginia Beach, Virginia, United States
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House Cape Charles
from $814 per night
House ∙ 12 guests ∙ 6 bedrooms
4.8
Outstanding(69 ratings)
Cape Charles, Northampton County, Virginia, United States
Vrbo
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House Chic's Beach
from $789 per night
House ∙ 21 guests ∙ 8 bedrooms
4.9
Outstanding(70 ratings)
Chic's Beach, Virginia Beach, Virginia, United States
Vrbo
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House West Ocean View
from $159 per night
House ∙ 4 guests ∙ 3 bedrooms
5.0
Outstanding(18 ratings)
West Ocean View, Norfolk, Virginia, United States
Vrbo
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House Dam Neck
from $442 per night
House ∙ 10 guests ∙ 5 bedrooms
4.2
Very good(24 ratings)
Dam Neck, Virginia Beach, Virginia, United States
Vrbo
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House Northeast Virginia Beach
from $437 per night
House ∙ 9 guests ∙ 4 bedrooms
4.8
Outstanding(54 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Vrbo
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House Cape Charles
from $551 per night
House ∙ 12 guests ∙ 4 bedrooms
4.9
Outstanding(25 ratings)
Cape Charles, Northampton County, Virginia, United States
Vrbo
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House Northside
from $110 per night
House ∙ 2 guests ∙ 2 bedrooms
4.9
Outstanding(39 ratings)
Northside, Norfolk, Virginia, United States
Vrbo
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House Woolford
from $332 per night
House ∙ 18 guests ∙ 6 bedrooms
5.0
Outstanding(13 ratings)
Woolford, Madison, Maryland, United States
Vrbo
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House Northeast Virginia Beach
from $535 per night
House ∙ 9 guests ∙ 4 bedrooms
4.7
Excellent(35 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Vrbo
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Villa Northeast Virginia Beach
from $93 per night
Villa ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding(2 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Vrbo
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House Willoughby Spit
from $343 per night
House ∙ 12 guests ∙ 5 bedrooms
4.8
Outstanding(22 ratings)
Willoughby Spit, Norfolk, Virginia, United States
Vrbo
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House East Ocean View
from $180 per night
House ∙ 10 guests ∙ 4 bedrooms
4.8
Outstanding(48 ratings)
East Ocean View, Norfolk, Virginia, United States
Vrbo
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House Cape Charles
from $407 per night
House ∙ 9 guests ∙ 4 bedrooms
5.0
Outstanding(44 ratings)
Cape Charles, Northampton County, Virginia, United States
Vrbo
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House Saint Michaels
from $873 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(2 ratings)
Saint Michaels, St. Michaels, Maryland, United States
Vrbo
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House Fort Story
from $113 per night
House ∙ 4 guests ∙ 2 bedrooms
Fort Story, Virginia Beach, Virginia, United States
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House Northeast Virginia Beach
from $995 per night
House ∙ 18 guests ∙ 8 bedrooms
4.4
Very good(6 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Vrbo
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House Virginia Beach
from $192 per night
House ∙ 4 guests ∙ 3 bedrooms
Virginia Beach, Virginia, United States
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House Edgewater
from $302 per night
House ∙ 10 guests ∙ 3 bedrooms
4.7
Excellent(23 ratings)
Edgewater, Anne Arundel County, Maryland, United States
Vrbo
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House Northeast Virginia Beach
from $592 per night
House ∙ 9 guests ∙ 4 bedrooms
4.8
Outstanding(20 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Vrbo
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Show all 11629 apartments in Chesapeake Bay

Price and Availability Index in Chesapeake Bay

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Vacation Rental Price Information in Chesapeake Bay

By constantly analyzing our data, we created a graph to show you the fluctuation of prices in Chesapeake Bay. Booking a vacation rental is most expensive in November. In the period 11/29 – 12/6, you will need to pay $629 on average. On the other hand, the cheapest month in the year is February, with an average vacation rental price of $362.

Rental availability information in Chesapeake Bay

This graph shows how many vacation rentals are available over the next 12 months. Only 5% of the vacation rentals in Chesapeake Bay are available in November. If you'd like to visit then, make sure to book early! You'll find the highest availability in July, with 56% of the vacation rentals in Chesapeake Bay still available.

2,417,475 reviews
2,417,475 travelers who stayed in Chesapeake Bay rated their vacation home 4.2/5 stars on average.

And we love our apartments

186 m² House
37 m² Cottage
242 m² House
232 m² Condo
House
Show all 11629 apartments in Chesapeake Bay

Features of Chesapeake Bay vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Internet, Pool and Pets allowed
🏊  Vacation rentals with a pool 4,604 rentals
🌙 Minimum price starting at $77
🐾 Pet friendly vacation homes 3,925 rentals
🏡 Rentals available 12,404 rentals

Beautiful regions abroad to consider for next trip

Beautiful regions near to consider for next trip

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