Vacation Rentals in Chesapeake Bay

Vacation Rentals in Chesapeake Bay

Start comparing over 543 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

Vacation Rentals in Chesapeake Bay

Vacation rental for 2 people, with pool in Chesapeake Bay
Vacation rental for 2 people, with pool
1 bedroom1.2mi to the beach
from $82 / night
Vacation rental for 2 people, with yard in Chesapeake Bay
Vacation rental for 2 people, with yard
5mi to the beach
5.0
from $173 / night
Vacation rental for 2 people, with pool in Chesapeake Bay
Vacation rental for 2 people, with pool
1 bedroom1.2mi to the beach
from $80 / night
Vacation rental for 2 people, with yard in Chesapeake Bay
Vacation rental for 2 people, with yard
1 bedroom6.5mi to the beach
5.0
(20 reviews)
from $181 / night

Popular Vacation Rentals in Chesapeake Bay

Vacation rental for 6 people in Chesapeake Bay
Vacation rental for 6 people
3 bedrooms1.9mi to the beach
4.8
(11 reviews)
from $224 / night
Vacation rental for 3 people, with pool and yard, with pets in Chesapeake Bay
Vacation rental for 3 people, with pool and yard, with pets
1 bedroom3.3mi to the beach
4.5
(57 reviews)
from $150 / night
Vacation rental for 4 people, with yard, with pets in Chesapeake Bay
Vacation rental for 4 people, with yard, with pets
2 bedrooms800yd to the beach
4.8
(20 reviews)
from $229 / night
Vacation rental for 2 people, with yard in Chesapeake Bay
Vacation rental for 2 people, with yard
1 bedroom
5.0
(3 reviews)
from $224 / night

Vacation rentals with free cancellation

Vacation rental for 12 people, with terrace, with pets in Chesapeake Bay
Vacation rental for 12 people, with terrace, with pets
4 bedrooms3.7mi to the beach
from $317 / nightFREE cancellation
Hotel for 2 people, with terrace, with pets in Chesapeake Bay
Hotel for 2 people, with terrace, with pets
1 bedroom1.5mi to the beach
4.5
(1167 reviews)
from $93 / nightFREE cancellation
Hotel for 2 people, with pool, with pets in Chesapeake Bay
Hotel for 2 people, with pool, with pets
1 bedroom2.5mi to the beach
3.9
(696 reviews)
from $54 / nightFREE cancellation
Hotel for 2 people, with pool and hot tub, kid friendly in Chesapeake Bay
Hotel for 2 people, with pool and hot tub, kid friendly
1 bedroom7.5mi to the beach
4.3
(807 reviews)
from $97 / nightFREE cancellation

Pet-friendly Vacation Rentals

Vacation rental for 2 people, with yard, with pets in Chesapeake Bay
Vacation rental for 2 people, with yard, with pets
1 bedroom3.4mi to the beach
4.0
from $207 / night
Vacation rental for 2 people, with ocean view in Chesapeake Bay
Vacation rental for 2 people, with ocean view
1 bedroom5.2mi to the beach
from $199 / night
Vacation rental for 2 people, with yard, with pets in Chesapeake Bay
Vacation rental for 2 people, with yard, with pets
5.0
(20 reviews)
from $124 / night
Vacation rental for 3 people, with yard, with pets in Chesapeake Bay
Vacation rental for 3 people, with yard, with pets
2 bedrooms6.7mi to the beach
4.9
(15 reviews)
from $88 / night

Vacation Rentals with Pool

Vacation rental for 2 people, with yard in Chesapeake Bay
Vacation rental for 2 people, with yard
1 bedroom
5.0
(7 reviews)
from $207 / night
Vacation rental for 2 people, with yard in Chesapeake Bay
Vacation rental for 2 people, with yard
1 bedroom
5.0
(16 reviews)
from $209 / night
Vacation rental for 2 people, with pool in Chesapeake Bay
Vacation rental for 2 people, with pool
4.9
(13 reviews)
from $248 / night
Vacation rental for 2 people, with pool in Chesapeake Bay
Vacation rental for 2 people, with pool
1 bedroom1.2mi to the beach
from $71 / night

Vacation Rentals with Internet

Vacation rental for 2 people in Chesapeake Bay
Vacation rental for 2 people
1 bedroom6.1mi to the beach
5.0
(15 reviews)
from $179 / night
Hotel for 2 people, with yard in Chesapeake Bay
Hotel for 2 people, with yard
2 bedrooms
5.0
(2 reviews)
from $598 / night
Vacation rental for 2 people, with yard in Chesapeake Bay
Vacation rental for 2 people, with yard
1 bedroom5mi to the beach
from $175 / night
Vacation rental for 2 people in Chesapeake Bay
Vacation rental for 2 people
1 bedroom0.9mi to the beach
4.9
(20 reviews)
from $218 / night

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 12
Internet 454
Pets allowed 176
Balcony/Terrace 151
TV 494
Air conditioning 508

Prices and availability

Prices

$788
August
September
October
November
December
January
February
March
April
May
June
July
Average price per week

Availabilities

75 %
August
September
October
November
December
January
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

What was the average price for a vacation rental on the Chesapeake Bay last year?

Considering the average cost of $393 per night, the Chesapeake Bay lies at the upper end of the price range for vacation rentals in the USA.

Which months allow you to save the most on vacation rentals?

According to last year, the months at the lowest possible cost on the Chesapeake Bay are February, March and April, with average prices of $334, $346, and $371, respectively.

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

When it comes to looking for a vacation rental on the Chesapeake Bay, the months that cost the most are, in order of highest to lowest, July, September and October, with average prices per night of $424, $420, and $420, respectively.

Is it necessary to plan a trip to the Chesapeake Bay well in advance?

When planning a vacation to the Chesapeake Bay, we recommend you to plan ahead as 81% of rentals are usually booked, according to the data from last year.

When are more vacation rentals available?

The months when it's easiest to find free accommodation on the Chesapeake Bay are January (the average amount of properties that are available reached 42% of the total last year), February (38%), and December (36%).

How many vacation rentals are there on the Chesapeake Bay?

We have 1,400 rentals for you on the Chesapeake Bay, provided by our 2 local and international partners.

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

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