Vacation Rentals in Chesapeake Bay

Vacation Rentals in Chesapeake Bay

Start comparing over 148162 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

Popular Vacation Rentals in Chesapeake Bay

Vacation rental for 12 people, with hot tub, kid friendly in Chesapeake Bay
from
$224
per night
Vacation rental for 12 people, with hot tub, kid friendly
12 pers.4 bedrooms500yd to the beach
4.0
(3 reviews)
Vacation rental for 6 people in Chesapeake Bay
from
$226
per night
Vacation rental for 6 people
6 pers.3 bedrooms1.9mi to the beach
4.8
(10 reviews)
Vacation rental for 6 people, with yard and hot tub as well as pool, kid friendly in Chesapeake Bay
from
$289
per night
Vacation rental for 6 people, with yard and hot tub as well as pool, kid friendly
6 pers.3 bedrooms1,798ft²1.8mi to the beach
4.8
(20 reviews)
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Vacation rentals with free cancellation

Vacation rental for 2 people, with yard and hot tub in Chesapeake Bay
from
$143
per night
Vacation rental for 2 people, with yard and hot tub
2 pers.1 bedroom172ft²
FREE cancellation
4.2
(51 reviews)
Vacation rental for 4 people, with yard, with pets in Chesapeake Bay
from
$168
per night
Vacation rental for 4 people, with yard, with pets
4 pers.1 bedroom3.3mi to the beach
FREE cancellation
4.5
(62 reviews)
Vacation rental for 6 people, with yard and view, kid friendly in Chesapeake Bay
from
$304
per night
Vacation rental for 6 people, with yard and view, kid friendly
6 pers.3 bedrooms1.1mi to the beach
FREE cancellation
4.9
(8 reviews)
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Vacation Rentals in Chesapeake Bay

Vacation rental for 8 people, with yard, kid friendly in Chesapeake Bay
from
$349
per night
Vacation rental for 8 people, with yard, kid friendly
8 pers.4 bedrooms0ft²1.8mi to the beach
4.8
(12 reviews)
Vacation rental for 8 people, with yard and ocean view, kid friendly in Chesapeake Bay
from
$133
per night
Vacation rental for 8 people, with yard and ocean view, kid friendly
8 pers.3 bedrooms1,195ft²0.9mi to the beach
5.0
(3 reviews)
Vacation rental for 12 people, kid friendly in Chesapeake Bay
from
$221
per night
Vacation rental for 12 people, kid friendly
12 pers.3 bedrooms700yd to the beach
4.0
Vacation rental for 10 people, with pets in Chesapeake Bay
from
$252
per night
Vacation rental for 10 people, with pets
10 pers.8.2mi to the beach
5.0
Vacation rental for 6 people, with view and yard in Chesapeake Bay
from
$202
per night
Vacation rental for 6 people, with view and yard
6 pers.3 bedrooms5.1mi to the beach
4.4
(15 reviews)
Vacation rental for 2 people, with view and yard in Chesapeake Bay
from
$238
per night
Vacation rental for 2 people, with view and yard
2 pers.1 bedroom1mi to the beach
FREE cancellation
4.7
(74 reviews)
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Pet-friendly Vacation Rentals

Vacation rental for 2 people, with terrace, with pets in Chesapeake Bay
from
$98
per night
Vacation rental for 2 people, with terrace, with pets
2 pers.1 bedroom140ft²1.1mi to the beach
4.3
(273 reviews)
Vacation rental for 2 people, with yard and hot tub, kid friendly in Chesapeake Bay
from
$241
per night
Vacation rental for 2 people, with yard and hot tub, kid friendly
2 pers.1 bedroom323ft²
5.0
(62 reviews)
Vacation rental for 2 people, with pool and yard as well as view, kid friendly in Chesapeake Bay
from
$135
per night
Vacation rental for 2 people, with pool and yard as well as view, kid friendly
2 pers.1 bedroom248ft²5.8mi to the beach
4.7
(61 reviews)
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Vacation Rentals with Pool

Vacation rental for 3 people, with pool and sauna as well as balcony and view in Chesapeake Bay
from
$81
per night
Vacation rental for 3 people, with pool and sauna as well as balcony and view
3 pers.1 bedroom
4.0
(2513 reviews)
Vacation rental for 2 people, with yard and hot tub as well as pool in Chesapeake Bay
from
$248
per night
Vacation rental for 2 people, with yard and hot tub as well as pool
2 pers.1 bedroom129ft²
FREE cancellation
4.6
(180 reviews)
Vacation rental for 10 people, with yard and pool as well as view, with pets in Chesapeake Bay
from
$976
per night
Vacation rental for 10 people, with yard and pool as well as view, with pets
10 pers.5 bedrooms5.2mi to the beach
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Vacation Rentals with Internet

Vacation rental for 5 people, with terrace in Chesapeake Bay
from
$165
per night
Vacation rental for 5 people, with terrace
5 pers.3 bedrooms9.1mi to the beach
4.2
(13 reviews)
Vacation rental for 2 people, with hot tub and yard in Chesapeake Bay
from
$125
per night
Vacation rental for 2 people, with hot tub and yard
2 pers.1 bedroom5.6mi to the beach
FREE cancellation
4.9
(22 reviews)
Vacation rental for 2 people, with view and yard, kid friendly in Chesapeake Bay
from
$134
per night
Vacation rental for 2 people, with view and yard, kid friendly
2 pers.1 bedroom140ft²5.3mi to the beach
FREE cancellation
4.8
(19 reviews)
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Find Vacation Rentals in Chesapeake Bay

Map

Highlights Chesapeake Bay

  • Chesapeake Bay
  • gorgeous picturesque of the city with a wide variety of outdoor activities
  • a tranquil place to relax alone or with your family
  • plenty of Chesapeake Bay's finest foods
  • Sandy public beaches
  • lifeguards

Most popular in Chesapeake Bay

Pool 77
Internet 281
Pets allowed 93
Balcony/Terrace 96
TV 282
Air conditioning 295

Prices and availability

Prices

$482
February
March
April
May
June
July
Average price per week

Availabilities

53 %
February
March
April
May
June
July
Percentage of available rentals

Vacation rentals in Chesapeake Bay

Scenic Oceanside rental locations

Chesapeake Bay is a well-known place for those seeking the perfect vacation experience. The town is located on a tranquil and picturesque river, a few kilometers from the northern upper reaches of the Susquehanna River to the outlet into the Atlantic Ocean. It is about 4.5 km wide at its narrowest point between Plum Point in Kent County. The Bay has already been traversed twice; a bridge connects Virginia Beach and Cape Charles in Maryland and Virginia across the Chesapeake Bay. The Bay is a life source that flows through Maryland and the other five states. Most rentals are available along the beautiful Bay with access to the ocean views, which provides a comfortable vacation.

Picturesque Oceanview

Escape the noise and hustles of life and enjoy a beautiful view of the Chester River from your rentals or on a cruise, available for all on the east bank of Maryland. The wonderful 65-foot River Packet, a beautifully 1920s-style tour boat with an open fire, an upper deck, a temperature-controlled salon, and adequate space for you, your friends and your family. There's more to come from this fantastic adventure. The vacation homes are near shopping centers for a memorable shopping tour. Also, connect with your soulmate, workmate through activities such as swimming, fishing, golfing and kayaking at Chesapeake Bay.

Vacation rentals in Chesapeake Bay

The area and getting around

Chesapeake Bay rich in plant and fauna

There are various species of flora and fauna that live in the Bay. Over 350 fish species, different species of waterfowl, 170 mollusk species, more than 2,600 plant species, and more than 15 aquatic grass species. With a vast range of outdoor activities, the surrounding Maryland and Virginia areas enjoy a lot. There are amazing restaurants and eateries, plenty of water activities, wildlife observation places, and a bay to bask in the sun. This naturalistic atmosphere creates a peaceful staycation.

Cultural festivals

There are many festivals around Chesapeake Bay, they include the national folk festival, which celebrates the traditional music, dance, craft, and food that captivates America's heart. The free-family event in Salisbury in September with dance pavilions, artisan, local and ethnic food, jury market, and seven amazing scenes are featuring more than 300 artists along the Vikomico River. Other activities to partake in, particularly with companions, are fishing, swimming, taking walks, or golfing.

Travelers and activities

Chesapeake Bay for food lovers

There are so many brilliant chefs and cafés in Chesapeake Bay. It's easy to fill your picnic basket with delectable cuisines to spice up your tour. to discuss the different cuisines in Chesapeake Bay without mentioning fish is impossible. While it's vital to learn about, appreciate, and study the range of foods available in the Chesapeake Bay, it's even more crucial to understand where the foods come from. The vacation rentals in Chesapeake Bay provide an opportunity to go away and learn about how seafood is gathered and prepared.

Duck for festival lovers

The landscape of Chesapeake Bay is dotted with various ethnic festivals all over the year. Your stay in Chesapeake Bay vacation rentals will give you a great chance to learn about the annual Kunta Kinte cultural festival, the "Bawlmer Hon, "and the Caribbean carnival and parades. The festivals are characterized by cultural music, crafts, and food.

„Did you know that Chesapeake Bay is an estuary. It is a mixture of freshwater and seawater. Now you know“

Top 5 travel tips for Chesapeake Bay

1. Visit the Arboretum and shop

The Adkins Arboretum is a serene and beautiful 400-hectare natural garden with indigenous plants and forest trails to enjoy long walks. The Botanic Gardens offers a range of guided walks, educational programs, lectures, art exhibitions, and seasonal social activities to encourage awareness and conservation of native flora in the Chesapeake Bay area. Gift shops and bookstores are available with unique shells, carvings, hats, shorts, or shirts to remember your vacation in Chesapeake Bay.

2. Visit the Academy Art Museum

Visit the well-preserved early 19th-century school building; it holds a collection of photographs, prints, and drawings of prominent figures of both local and international artists, hosting a series of concerts, dances, and historical lectures.

3. Sunbathing and food tasting

There are many wonderful restaurants to enjoy local and international cuisines. Enjoy the sun and the sunset at the rentals or an outdoor setting as you enjoy your food.

4. Parasailing, Surfing and fishing

Enjoy the challenging waves by Surfing and the best parasailing experience. The parasail journey will allow you to see various rare gorgeous birds. You only enjoy this once-in-a-lifetime. Take your family or spouse and enjoy an unforgettable experience.

5. visit the C&D Canal Museum

Many engaging videos and thrilling scenes from the Canal's construction and interesting displays are available at the museum. Chesapeake Bay should be your next trip for the best outdoor activities to enjoy and have fun

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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