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Chesapeake Bay Vacation Rentals

Find 5,850 available offers from 16 partners
Chesapeake Bay
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Up to $100
$100 - $199
From $200
Accommodation types
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Outstanding: 4.5+
Very Good: 4+
Good: 3.5+
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Best Vacation Home Deals in Chesapeake Bay

Condo Northeast Virginia Beach
Oct 8 - Oct 15
-97%
$3,941
$111 per night
Condo ∙ 4 guests ∙ 1 bedroom
3.8/5.0 "Good"
(2239 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Details
getaroom.com
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Condo Northeast Virginia Beach
Dec 4 - Dec 11
-75%
$405
$103 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.0/5.0 "Very good"
(1890 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Details
FindHotel
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Condo Northeast Virginia Beach
Nov 13 - Nov 20
-49%
$228
$117 per night
Condo ∙ 4 guests ∙ 1 bedroom
3.9/5.0 "Good"
(2231 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Details
Get a Room
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Find a vacation rental that meets your criteria among the 5850 welcoming accommodations from 17 partner websites in Chesapeake Bay. HomeToGo instantaneously presents you with the best offers by comparing all of the listed accommodations in Chesapeake Bay from 17 different providers.

Recommended Vacation Rentals in Chesapeake Bay

Find your perfect vacation rental in Chesapeake Bay: from $73 per night

House Northeast Virginia Beach
Sep 11 - Sep 18
$210 per night
House ∙ 6 guests ∙ 2 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Details
RedAwning
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House Northeast Virginia Beach
Nov 6 - Nov 13
$433 per night
House ∙ 8 guests ∙ 3 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Details
RedAwning
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Condo Northeast Virginia Beach
Jan 8 - Jan 15
$1,313 per night
Condo ∙ 4 guests ∙ 1 bedroom
3.8/5.0 "Good"
(2241 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Details
FindHotel
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House Northeast Virginia Beach
Dec 4 - Dec 11
$207 per night
House ∙ 6 guests ∙ 2 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Details
RedAwning
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Condo Northeast Virginia Beach
Dec 4 - Dec 11
-75%
$405
$103 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.0/5.0 "Very good"
(1894 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Details
FindHotel
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Aparthotel Northwest
Nov 1 - Nov 8
-53%
$193
$91 per night
Aparthotel ∙ 2 guests ∙ 1 bedroom
3.9/5.0 "Good"
(882 ratings)
Northwest, Virginia Beach, Virginia, United States
Details
Expedia
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Condo Northeast Virginia Beach
Jan 15 - Jan 22
-50%
$228
$114 per night
Condo ∙ 4 guests ∙ 1 bedroom
3.9/5.0 "Good"
(2233 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Details
Get a Room
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Resort Northeast Virginia Beach
Jan 1 - Jan 8
-73%
$322
$87 per night
Resort ∙ 4 guests ∙ 1 bedroom
4.3/5.0 "Very good"
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Details
Agoda
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Apartment Northeast Virginia Beach
Nov 6 - Nov 13
$176 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Free cancellation
Details
TripAdvisor
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Vacation rentals with Wi-Fi

House Internet Northeast Virginia Beach
Aug 21 - Aug 28
$223 per night
House ∙ 6 guests ∙ 2 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Internet
Details
RedAwning
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House Internet Northeast Virginia Beach
Aug 21 - Aug 28
$254 per night
House ∙ 6 guests ∙ 3 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Internet
Details
RedAwning
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House Internet Northeast Virginia Beach
Aug 21 - Aug 28
$598 per night
House ∙ 8 guests ∙ 3 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Internet
Details
RedAwning
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Vacation rentals and apartments with air conditioning

Apartment Aircondition Northeast Virginia Beach
Oct 2 - Oct 9
$80 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.2/5.0 "Very good"
(266 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Aircondition
Details
Expedia
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Resort Aircondition Northeast Virginia Beach
Oct 2 - Oct 9
-72%
$456
$127 per night
Resort ∙ 4 guests ∙ 1 bedroom
4.3/5.0 "Very good"
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Aircondition
Details
Agoda
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Condo Aircondition Northeast Virginia Beach
Jan 15 - Jan 22
-63%
$307
$114 per night
Condo ∙ 4 guests ∙ 1 bedroom
3.9/5.0 "Good"
(2142 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Aircondition
Details
Get a Room
View deal
See all offers

Apartments and vacation rentals with a kitchen

Condo Kitchen ViBe Creative District
Aug 21 - Aug 28
$184 per night
Condo ∙ 8 guests ∙ 2 bedrooms
ViBe Creative District, Virginia Beach, Virginia, United States
Kitchen
Details
Expedia
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Apartment Kitchen Annapolis
Aug 21 - Aug 28
$686 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
Details
TripAdvisor
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House Kitchen Accomack County
May 21 - May 28
$136 per night
House ∙ 5 guests ∙ 3 bedrooms
Accomack County, Virginia, United States
Kitchen
Details
TripAdvisor
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Popular Rental Amenities in Chesapeake Bay

  • Internet (4,775)
  • No smoking (4,623)
  • Air conditioning (3,966)
  • TV (3,735)
  • Wheelchair access (3,478)
  • Pool (2,833)
  • Microwave (2,601)
  • No pets (1,874)
  • Balcony/Patio (1,308)
  • Pet allowed (1,289)
  • Kitchen (1,190)
  • Crib (828)

Using our filters will help you find the perfect vacation rental in Chesapeake Bay. HomeToGo's data highlights that "internet" and "TVs" turn out to be the most frequently offered features in Chesapeake Bay. Plan your vacation in advance if you love sweating the stress away in saunas or you like to end your days curled up by the fire. There are just 190 listed accommodations providing "saunas" and 394 properties including "fireplaces."

The Weather in Chesapeake Bay

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43°
28°
13 days 13
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45°
30°
13 days 13
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55°
37°
12 days 12
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66°
46°
12 days 12
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75°
59°
13 days 13
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84°
66°
12 days 12
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88°
72°
11 days 11
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84°
68°
13 days 13
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79°
63°
11 days 11
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68°
52°
12 days 12
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57°
41°
9 days 9
max.
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54°
37°
13 days 13
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

The above is a climate diagram for Chesapeake Bay. During July, maximum temperatures go up to more than 87° However, temperatures can go lower than 28° in Chesapeake Bay in January. The rainiest month is January while the driest month is November.

Accommodations for your vacation in Chesapeake Bay

3,725 out of the 5822 listed properties in Chesapeake Bay are hotel rooms. They account for many of the properties in this destination (62.98%). Additionally, these accommodations have an average size of 400 ft² as well as a median price of $214 per night. Moreover, if you are going in a group of 4, hotel rooms are the perfect accommodation type in Chesapeake Bay, as they usually welcome this exact group size. You can also search and find other accommodation types in Chesapeake Bay. Bed & Breakfast rentals are, for example, another popular accommodation option there with 415 properties to compare. These accommodations cost $294 per night on average and have an average size of 720 ft².

Revel in the laidback atmosphere of Chesapeake Bay vacation rentals

Chesapeake Bay, Maryland’s most famous estuary, is actually quite big – approximately 200 miles long. It is home to historical attractions such as Fort McHenry and Chesapeake Bay Maritime Museum, as well as natural attractions such as Blackwater National Wildlife Refuge and Calvert Cliffs.

Chesapeake Bay vacation homes are available in different types and sizes. From luxury townhouses and waterfront cottages to apartments and farmhouses, vacation rentals in Chesapeake Bay are available to suit your every need and desire.

Show all 5,850 properties
What is the weather like in Chesapeake Bay?

Ideal time to visit Chesapeake Bay

The peak season for travelers to Chesapeake Bay is the summer period between June and August. Thousands of holidaymakers visit during this time for the hot weather and fun water-sports, including fishing, boating, and swimming.

If you specifically want to avoid the peak crowds, travel to Chesapeake Bay in either spring (March to May) or fall (September to November). During these seasons, you will be able to observe dolphins, explore salt marshes, and go hiking.

What are the best events and festivals in Chesapeake Bay?

Festivals in Chesapeake Bay

Chesapeake Bay Blues Festival is an annual event that takes place in Annapolis, Maryland. Spanning a weekend, this festival raises millions of dollars for charity. Attend this event and you can enjoy some of the world's best blues artists accompanied by gorgeous beachside views and amazing food.

Maryland Seafood Festival is held to celebrate the state's signature blue crabs. This festival also takes place in Annapolis and features numerous vendors selling crab cakes, steamed crab, and cream of crab soup, as well as braided crab pretzels.

What are the must-see attractions in Chesapeake Bay?

Iconic attractions in Chesapeake Bay

Chesapeake Bay Bridge-Tunnel

Located on US Route 13, Chesapeake Bay Bridge-Tunnel is a fixed link crossing in Virginia. This bridge-tunnel includes two mile-long tunnels and was opened in 1964. The structure is one of only ten bridge-tunnel constructions in the world.

Thomas Point Shoal Light

Thomas Point Shoal Light is the most popular lighthouse in Maryland. Built in 1825, it was listed on the National Register of Historic Places in 1975. It is open to the public for just 3 months in the year.

Susquehanna

Susquehanna is the longest river in the continental US, and the Chesapeake Bay is actually the ria of this river. The Susquehanna River and the Chesapeake Bay are essentially part of one ecosystem.

Chesapeake Bay Bridge

Chesapeake Bay Bridge is an important link along US Routes 50 and 301. This bridge spans Chesapeake Bay in its entirety and connects the metropolitan Western Shore to the rural Eastern Shore in Maryland.

Kent Island

Situated at the base of Chesapeake Bay Bridge, Kent Island is home to beautiful views and numerous dining options. Kent Narrows is a small water channel that separates this island from the mainland.

How much does it cost to rent a vacation rental in Chesapeake Bay?

The price for Hotel rooms and Bed & Breakfast rentals in Chesapeake Bay is $72 per night.

How many vacation rentals are available to book in Chesapeake Bay?

August has the highest amount of available Hotel rooms and Bed & Breakfast rentals in Chesapeake Bay, so you can expect plenty of offers, even for last-minute bookings.

What amenities are most popular for vacation homes in Chesapeake Bay?

The most popular amenities for home rentals in Chesapeake Bay include accommodations that have: internet, TVs, and pools.

How many vacation rentals are in Chesapeake Bay?

Discover 5822 vacation rentals available to book in Chesapeake Bay.

What's the best time of year to travel to Chesapeake Bay?

Chesapeake Bay has its warmest time of year around July and June, with average nightly prices being around $72.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Chesapeake Bay TripAdvisor Vacation Rentals in Chesapeake Bay Vrbo Vacation Rentals in Chesapeake Bay Airbnb Vacation Rentals in Chesapeake Bay VacationRentals.com Vacation Rentals in Chesapeake Bay HouseTrip Vacation Rentals in Chesapeake Bay FlipKey Vacation Rentals in Chesapeake Bay 9flats.com Vacation Rentals in Chesapeake Bay PerfectPlaces.com Vacation Rentals in Chesapeake Bay Homestay.com Vacation Rentals in Chesapeake Bay Only-apartments Vacation Rentals in Chesapeake Bay Interhome Vacation Rentals in Chesapeake Bay Bedycasa Vacation Rentals in Chesapeake Bay Novasol Vacation Rentals in Chesapeake Bay HomeEscape Vacation Rentals in Chesapeake Bay

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