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

Chesapeake Bay Vacation Rentals

Chesapeake Bay
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Chesapeake Bay
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Best-rated vacation rentals in Chesapeake Bay

Discover vacation rentals with top-notch guest ratings

House Bay View
$110 per night
House ∙ 10 guests ∙ 4 bedrooms
4.5
Excellent (12 ratings)
Bay View, Norfolk, Virginia, United States
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House Taylors Island
$606 per night
House ∙ 14 guests ∙ 5 bedrooms
5.0
Outstanding (32 ratings)
Taylors Island, Dorchester County, Maryland, United States
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House Deal Island
$140 per night
House ∙ 8 guests ∙ 3 bedrooms
4.7
Excellent (41 ratings)
Deal Island, Somerset County, Maryland, United States
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Pet-friendly rentals in Chesapeake Bay

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

Cottage Wenona
$98 per night
Cottage ∙ 8 guests ∙ 4 bedrooms
4.7
Excellent (79 ratings)
Wenona, Deal Island, Maryland, United States
Pet-friendly
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House Saint Michaels
$546 per night
House ∙ 8 guests ∙ 4 bedrooms
Saint Michaels, St. Michaels, Maryland, United States
Pet-friendly
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Cabin Lusby
$417 per night
Cabin ∙ 11 guests ∙ 4 bedrooms
5.0
Outstanding (5 ratings)
Lusby, Solomons Island, Maryland, United States
Pet-friendly
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Accommodation with Internet in Chesapeake Bay

Choose your ideal rental with Internet and WiFi in Chesapeake Bay

Cottage Scotland
$240 per night
Cottage ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding (16 ratings)
Scotland, St. Inigoes, Maryland, United States
Internet
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House Algonquin
$674 per night
House ∙ 13 guests ∙ 5 bedrooms
4.9
Outstanding (14 ratings)
Algonquin, Cambridge, Maryland, United States
Internet
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House Chesapeake Beach
$174 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (1 rating)
Chesapeake Beach, Sunderland, Maryland, United States
Internet
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Vacation rentals with pool in Chesapeake Bay

Discover best cabin and house rentals with pool in Chesapeake Bay

House Exmore
$431 per night
House ∙ 12 guests ∙ 4 bedrooms
4.9
Outstanding (46 ratings)
Exmore, Northampton County, Virginia, United States
Pool
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House Easton
$317 per night
House ∙ 10 guests ∙ 5 bedrooms
3.0
(1 rating)
Easton, Talbot County, Maryland, United States
Pool
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House Cape Charles
$416 per night
House ∙ 11 guests ∙ 4 bedrooms
5.0
Outstanding (1 rating)
Cape Charles, Northampton County, Virginia, United States
Pool
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Best vacation rental offers in Chesapeake Bay

Cottage Deal Island
$166 per night
Cottage ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (65 ratings)
Deal Island, Somerset County, Maryland, United States
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House North
$590 per night
House ∙ 10 guests ∙ 6 bedrooms
5.0
Outstanding (17 ratings)
North, Petsworth, Virginia, United States
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House Virginia Beach
$237 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (3 ratings)
Virginia Beach, Virginia, United States
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House Deltaville
$361 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (20 ratings)
Deltaville, Pine Top, Virginia, United States
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House Cambridge
$914 per night
House ∙ 22 guests ∙ 8 bedrooms
4.8
Outstanding (91 ratings)
Cambridge, Dorchester County, Maryland, United States
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House Cape Charles
$366 per night
House ∙ 8 guests ∙ 3 bedrooms
4.5
Excellent (12 ratings)
Cape Charles, Northampton County, Virginia, United States
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House White Stone
$355 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (10 ratings)
White Stone, Lancaster County, Virginia, United States
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House Reedville
$532 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding (96 ratings)
Reedville, Northumberland County, Virginia, United States
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Cottage Deltaville
$214 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (10 ratings)
Deltaville, Pine Top, Virginia, United States
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House Heathsville
$199 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (104 ratings)
Heathsville, Northumberland County, Virginia, United States
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House Buckroe Beach
$139 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (1 rating)
Buckroe Beach, Hampton, Virginia, United States
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House Cape Charles
$544 per night
House ∙ 15 guests ∙ 6 bedrooms
4.9
Outstanding (57 ratings)
Cape Charles, Northampton County, Virginia, United States
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House Chesapeake Beach
$218 per night
House ∙ 9 guests ∙ 4 bedrooms
5.0
Outstanding (20 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
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Farmhouse Taylors Island
$562 per night
Farmhouse ∙ 14 guests ∙ 4 bedrooms
4.9
Outstanding (92 ratings)
Taylors Island, Dorchester County, Maryland, United States
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House Wenona
$93 per night
House ∙ 5 guests ∙ 2 bedrooms
4.8
Outstanding (70 ratings)
Wenona, Deal Island, Maryland, United States
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House Dameron
$277 per night
House ∙ 9 guests ∙ 3 bedrooms
4.9
Outstanding (94 ratings)
Dameron, St. Inigoes, Maryland, United States
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Cottage Saint Michaels
$422 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Saint Michaels, St. Michaels, Maryland, United States
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House Cape Charles
$188 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding (8 ratings)
Cape Charles, Northampton County, Virginia, United States
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House Cambridge
$279 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (47 ratings)
Cambridge, Dorchester County, Maryland, United States
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House Deltaville
$241 per night
House ∙ 10 guests ∙ 4 bedrooms
4.7
Excellent (38 ratings)
Deltaville, Pine Top, Virginia, United States
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House Northeast Virginia Beach
$451 per night
House ∙ 9 guests ∙ 4 bedrooms
5.0
Outstanding (10 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
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Boat Stevensville
$196 per night
Boat ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (3 ratings)
Stevensville, Kent Island, Maryland, United States
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House Taylors Island
$427 per night
House ∙ 15 guests ∙ 5 bedrooms
4.9
Outstanding (25 ratings)
Taylors Island, Dorchester County, Maryland, United States
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House Tipers
$237 per night
House ∙ 8 guests ∙ 3 bedrooms
4.8
Outstanding (72 ratings)
Tipers, Northumberland County, Virginia, United States
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House Reedville
$110 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (12 ratings)
Reedville, Northumberland County, Virginia, United States
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Cottage Scotland
$515 per night
Cottage ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (2 ratings)
Scotland, St. Inigoes, Maryland, United States
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House Cape Charles
$301 per night
House ∙ 8 guests ∙ 3 bedrooms
4.6
Excellent (42 ratings)
Cape Charles, Northampton County, Virginia, United States
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House Cape Charles
$198 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (18 ratings)
Cape Charles, Northampton County, Virginia, United States
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House Buckroe Beach
$426 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (23 ratings)
Buckroe Beach, Hampton, Virginia, United States
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House Norfolk Garden
$89 per night
House ∙ 5 guests ∙ 3 bedrooms
4.8
Outstanding (8 ratings)
Norfolk Garden, Norfolk, Virginia, United States
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House Willoughby Spit
$292 per night
House ∙ 11 guests ∙ 5 bedrooms
5.0
Outstanding (8 ratings)
Willoughby Spit, Norfolk, Virginia, United States
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House Reedville
$446 per night
House ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (109 ratings)
Reedville, Northumberland County, Virginia, United States
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Farmhouse Crisfield
$300 per night
Farmhouse ∙ 12 guests ∙ 5 bedrooms
4.8
Outstanding (128 ratings)
Crisfield, Somerset County, Maryland, United States
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House Cambridge
$613 per night
House ∙ 13 guests ∙ 5 bedrooms
5.0
Outstanding (8 ratings)
Cambridge, Dorchester County, Maryland, United States
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House Cape Charles
$233 per night
House ∙ 6 guests ∙ 3 bedrooms
4.8
Outstanding (147 ratings)
Cape Charles, Northampton County, Virginia, United States
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House Selby-on-the-Bay
$295 per night
House ∙ 9 guests ∙ 5 bedrooms
4.3
Very good (14 ratings)
Selby-on-the-Bay, Anne Arundel County, Maryland, United States
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House Heathsville
$554 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (4 ratings)
Heathsville, Northumberland County, Virginia, United States
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House Cape Charles
$159 per night
House ∙ 9 guests ∙ 2 bedrooms
5.0
Outstanding (26 ratings)
Cape Charles, Northampton County, Virginia, United States
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House Fishing Creek
$282 per night
House ∙ 15 guests ∙ 5 bedrooms
4.9
Outstanding (127 ratings)
Fishing Creek, Hoopers Island, Maryland, United States
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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 August. In the period 8/24 – 8/31, you will need to pay $509 on average. On the other hand, the cheapest month in the year is February, with an average vacation rental price of $338.

Rental availability information in Chesapeake Bay

This graph shows how many vacation rentals are available over the next 12 months. Only 8% of the vacation rentals in Chesapeake Bay are available in January. If you'd like to visit then, make sure to book early! You'll find the highest availability in March, with 71% of the vacation rentals in Chesapeake Bay still available.

14 reviews
14 travelers who stayed in Chesapeake Bay rated their vacation home 3.7/5 stars on average.

And we love our apartments

89 m² Cottage
297 m² House
House
114 m² House
321 m² House
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Beautiful regions abroad to consider for next trip

Beautiful regions near to consider for next trip

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