Find Vacation Rentals in Chesapeake Bay

We have 9,692 properties to choose from
Chesapeake Bay
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Chesapeake Bay
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Popular Chesapeake Bay Vacation Rentals

Find the perfect Chesapeake Bay vacation rental

House Bay View
$245 per night
House ∙ 10 guests ∙ 4 bedrooms
4.6
Excellent (14 ratings)
Bay View, Norfolk, Virginia, United States
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Vrbo
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House Easton
$290 per night
House ∙ 10 guests ∙ 5 bedrooms
3.0
(1 rating)
Easton, Talbot County, Maryland, United States
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Vrbo
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House Reedville
$432 per night
House ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (109 ratings)
Reedville, Northumberland County, Virginia, United States
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Vrbo
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Cabin Lusby
$323 per night
Cabin ∙ 11 guests ∙ 4 bedrooms
5.0
Outstanding (5 ratings)
Lusby, Solomons Island, Maryland, United States
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Vrbo
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Cottage Scotland
$400 per night
Cottage ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding (17 ratings)
Scotland, St. Inigoes, Maryland, United States
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Vrbo
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Cottage Exmore
$202 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (28 ratings)
Exmore, Northampton County, Virginia, United States
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Vrbo
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House Reedville
$177 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (12 ratings)
Reedville, Northumberland County, Virginia, United States
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Vrbo
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House California
$390 per night
House ∙ 9 guests ∙ 4 bedrooms
4.7
Excellent (60 ratings)
California, Bay, Maryland, United States
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Vrbo
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Cottage White Stone
$154 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
3.6
Good (155 ratings)
White Stone, Lancaster County, Virginia, United States
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Vrbo
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Apartments and vacation rentals with a kitchen

House  East Ocean View
-6%
$382
$358 per night
House ∙ 8 guests ∙ 4 bedrooms
4.8
Outstanding (56 ratings)
East Ocean View, Norfolk, Virginia, United States
Kitchen
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Vrbo
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House  Ridge
$640 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding (126 ratings)
Ridge, St. Inigoes, Maryland, United States
Kitchen
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Vrbo
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House  Deale
$303 per night
House ∙ 10 guests ∙ 4 bedrooms
4.9
Outstanding (134 ratings)
Deale, Anne Arundel County, Maryland, United States
Kitchen
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Vrbo
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Vacation rentals with Wi-Fi

House  North
$529 per night
House ∙ 10 guests ∙ 6 bedrooms
5.0
Outstanding (18 ratings)
North, Petsworth, Virginia, United States
Internet
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Vrbo
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House  Foster
$511 per night
House ∙ 10 guests ∙ 6 bedrooms
5.0
Outstanding (54 ratings)
Foster, Westville, Virginia, United States
Internet
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Vrbo
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House  North Beach
$118 per night
House ∙ 3 guests ∙ 1 bedroom
4.8
Outstanding (42 ratings)
North Beach, Sunderland, Maryland, United States
Internet
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Vrbo
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Vacation Homes With Terraces

Cottage  Deltaville
$170 per night
Cottage ∙ 8 guests ∙ 2 bedrooms
5.0
Outstanding (66 ratings)
Deltaville, Pine Top, Virginia, United States
Balcony/Patio
Details
Vrbo
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Cottage  East Ocean View
$41 per night
Cottage ∙ 2 guests ∙ 1 bedroom
4.5
Excellent (98 ratings)
East Ocean View, Norfolk, Virginia, United States
Balcony/Patio
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Vrbo
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House  Willoughby Spit
$560 per night
House ∙ 12 guests ∙ 5 bedrooms
4.7
Excellent (79 ratings)
Willoughby Spit, Norfolk, Virginia, United States
Balcony/Patio
Details
Vrbo
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Frequently Asked Questions

What is the average price per night for accommodation in Chesapeake Bay?

Accommodation in Chesapeake Bay cost from $42 per night.

Is it possible to find vacation rentals in Chesapeake Bay?

On tripping.com, you will find 9,692 available vacation rental offers in Chesapeake Bay.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Chesapeake Bay

Looking for a vacation rental in Chesapeake Bay? Tripping.com has 45864 vacation rental homes available in Chesapeake Bay. You'll find 284 studios, 13942 1-bedroom, 9388 2-bedroom and 22250 rentals with 3 or more bedrooms ranging from $25 a night. For extra convenience, many of these vacation homes can be booked directly online. The average price of a nightly rental in Chesapeake Bay is $277 while the average price of a weekly rental is $2532. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Chesapeake Bay home is $2353. Wondering if you can bring your dog or cat along with you? There are 7104 pet-friendly vacation rentals available in Chesapeake Bay. In addition to accommodating pets, Chesapeake Bay rentals offer a variety of amenities. In particular, 39082 rentals have Internet and WiFi, 39889 have TV and/or cable and 17180 have a pool or hot tub. Search properties from 14 vacation rental sites in Chesapeake Bay where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 22046 HomeAway rentals, 10442 TripAdvisor short term rentals and 4421 Booking.com vacation rentals.
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