Vacation Rentals in Chesapeake Bay

Vacation Rentals in Chesapeake Bay

Start comparing over 247 rentals in Chesapeake Bay and book at the best price!

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Free cancellation
Vacation house
Vacation apartment
Pool
Internet
Pets allowed
4.0
& higher
4.5
& higher

Popular Vacation Rentals in Chesapeake Bay

from
$183
per night
Vacation rental for 6 people, with garden
6 pers.3 bedrooms1,399ft²5.2mi to the beach
FREE cancellation
5.0
(20 reviews)
from
$339
per night
Vacation rental for 6 people, with garden and pool as well as jacuzzi, child-friendly
6 pers.3 bedrooms1,798ft²1.8mi to the beach
FREE cancellation
4.8
(20 reviews)
from
$134
per night
Vacation rental for 8 people, with garden and ocean view, child-friendly
8 pers.3 bedrooms1,195ft²0.9mi to the beach
FREE cancellation
5.0
(3 reviews)
show all

Vacation rentals with free cancellation

from
$1,005
per night
Vacation rental for 9 people
9 pers.5 bedrooms1.7mi to the beach
FREE cancellation
from
$92
per night
Cottage for 4 people, with garden
4 pers.2 bedrooms893ft²6.9mi to the beach
FREE cancellation
5.0
(20 reviews)
from
$570
per night
Vacation rental for 15 people, with garden, child-friendly
15 pers.6 bedrooms5,995ft²6.5mi to the beach
FREE cancellation
5.0
(8 reviews)
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Vacation Rentals in Chesapeake Bay

from
$344
per night
Vacation rental for 8 people, with garden, child-friendly
8 pers.4 bedrooms0ft²1.8mi to the beach
FREE cancellation
4.8
(12 reviews)
from
$380
per night
Vacation rental for 10 people, with garden
10 pers.4 bedrooms2,562ft²1mi to the beach
4.0
(2 reviews)
from
$297
per night
Vacation rental for 10 people, with jacuzzi and garden as well as pool
10 pers.4 bedrooms4.9mi to the beach
FREE cancellation
5.0
(6 reviews)
from
$1,117
per night
Vacation rental for 12 people, with garden, child-friendly
12 pers.6 bedrooms
4.0
from
$99
per night
Vacation rental for 4 people, with balcony
4 pers.2 bedrooms646ft²700yd to the beach
FREE cancellation
from
$188
per night
Vacation rental for 8 people, with jacuzzi and garden, child-friendly
8 pers.3 bedrooms1,776ft²2.3mi to the beach
5.0
(20 reviews)
show all

Pet-friendly Vacation Rentals

from
$421
per night
Vacation rental for 18 people, with garden, with pets
18 pers.7 bedrooms3,035ft²
FREE cancellation
4.8
(6 reviews)
from
$435
per night
Vacation rental for 6 people
6 pers.3 bedrooms1,873ft²1.9mi to the beach
FREE cancellation
4.8
(9 reviews)
from
$507
per night
Vacation rental for 12 people, with garden, child-friendly
12 pers.5 bedrooms3,800ft²2.8mi to the beach
FREE cancellation
4.5
(21 reviews)
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Vacation Rentals with Pool

from
$784
per night
Vacation rental for 14 people, with pool
14 pers.6 bedrooms4,596ft²4.3mi to the beach
FREE cancellation
5.0
(19 reviews)
from
$260
per night
Vacation rental for 6 people, with balcony and pool
6 pers.3 bedrooms5.2mi to the beach
FREE cancellation
from
$762
per night
Vacation rental for 15 people, with garden and pool, child-friendly
15 pers.6 bedrooms
FREE cancellation
5.0
(20 reviews)
show all

Vacation Rentals with Internet

from
$228
per night
Vacation rental for 9 people, with garden, child-friendly
9 pers.3 bedrooms1,798ft²5.3mi to the beach
FREE cancellation
5.0
(20 reviews)
from
$293
per night
Vacation rental for 10 people, with balcony
10 pers.3 bedrooms2,293ft²6mi to the beach
FREE cancellation
5.0
(14 reviews)
from
$441
per night
Vacation rental for 8 people, with garden
8 pers.3 bedrooms1,798ft²
5.0
show all

Find Vacation Rentals in Chesapeake Bay

Map

Most popular in Chesapeake Bay

Pool 85
Internet 269
Pets allowed 94
Balcony/Terrace 93
TV 266
Air conditioning 262

Prices and availability

Prices

November
December
January
February
March
$428
Average price per week

Availabilities

November
December
January
February
March
68 %
Percentage of available rentals

FAQs: Vacation Rentals in Chesapeake Bay

How much do you pay, on average, for vacation rentals on the Chesapeake Bay?

Our data shows that the Chesapeake Bay has an average price of $388.02 per night, a relatively high one compared to the destinations in the USA.

What time of year offers, on average, the best vacation rental prices on the Chesapeake Bay?

]If you would like to get the most out of your money, the most budget-friendly months to visit the Chesapeake Bay are February ($322.07 the average per night for accommodation), December ($325.67), and March ($331.4).

During which months are vacation rentals more expensive on the Chesapeake Bay?

In 2020, the month that offered the highest average prices on the Chesapeake Bay was July, with an average price of $475.42 per night. This was followed by August, with an average of $467.34, and April, with $446.36.

Should I plan a trip to the Chesapeake Bay well in advance?

It is better to book your stay well in advance when visiting the Chesapeake Bay, as only 21% of our properties are usually available throughout the year.

What time of the year can I find more available vacation rentals?

The months when it's the easiest to find free accommodation on the Chesapeake Bay are April (the average amount of properties that are available reached 46% of the total in 2020), May (37.8%), and January (33.4%).

When are fewer rentals available on the Chesapeake Bay?

The accommodations on the Chesapeake Bay reach their peak in demand in August, with an availability rate of 5.6%. The second most requested month is July, with 6.25%, and the third is September with 9.25%.

How many rentals does Holidu have on the Chesapeake Bay?

Our catalog features around 100 properties from 3 partners, giving you plenty of choices when searching for your next dream vacation rental!

Holidu compares hundreds of websites to find your perfect holiday rental for the best price.

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