Find Vacation Rentals in 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 Arundel on the Bay
$413 per night
House ∙ 13 guests ∙ 5 bedrooms
4.3
Very good (32 ratings)
Arundel on the Bay, Anne Arundel County, Maryland, United States
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Vrbo
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House Lake Shore
$129 per night
House ∙ 15 guests ∙ 5 bedrooms
4.9
Outstanding (64 ratings)
Lake Shore, Anne Arundel County, Maryland, United States
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Vrbo
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House Deal Island
$147 per night
House ∙ 8 guests ∙ 3 bedrooms
4.7
Excellent (39 ratings)
Deal Island, Somerset County, Maryland, United States
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Vrbo
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House East Ocean View
$326 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (6 ratings)
East Ocean View, Norfolk, Virginia, United States
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Vrbo
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House Cape Saint Claire
$169 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (50 ratings)
Cape Saint Claire, Anne Arundel County, Maryland, United States
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Vrbo
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House Ewell
$174 per night
House ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding (1 rating)
Ewell, Smith Island, Maryland, United States
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Vrbo
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House Cape Charles
$137 per night
House ∙ 8 guests ∙ 2 bedrooms
4.8
Outstanding (27 ratings)
Cape Charles, Northampton County, Virginia, United States
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Vrbo
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House Taylors Island
$404 per night
House ∙ 15 guests ∙ 5 bedrooms
4.9
Outstanding (25 ratings)
Taylors Island, Dorchester County, Maryland, United States
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Vrbo
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Apartment Earleville
$131 per night
Apartment ∙ 3 guests ∙ 1 bedroom
4.9
Outstanding (10 ratings)
Earleville, Cecilton, Maryland, United States
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Vrbo
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Vacation rentals and apartments with air conditioning

House  Cape Charles
$549 per night
House ∙ 15 guests ∙ 6 bedrooms
4.9
Outstanding (51 ratings)
Cape Charles, Northampton County, Virginia, United States
Air conditioning
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Vrbo
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House  Elkton
$477 per night
House ∙ 8 guests ∙ 4 bedrooms
4.8
Outstanding (81 ratings)
Elkton, Cecil County, Maryland, United States
Air conditioning
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Vrbo
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House  Cape Charles
$327 per night
House ∙ 9 guests ∙ 3 bedrooms
4.9
Outstanding (10 ratings)
Cape Charles, Northampton County, Virginia, United States
Air conditioning
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Vrbo
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Vacation Homes With Terraces

Cottage  Elkton
$215 per night
Cottage ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (55 ratings)
Elkton, Cecil County, Maryland, United States
Balcony/Patio
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Vrbo
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House  Deltaville
$155 per night
House ∙ 12 guests ∙ 6 bedrooms
5.0
Outstanding (14 ratings)
Deltaville, Pine Top, Virginia, United States
Balcony/Patio
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Vrbo
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House  Rock Hall
$247 per night
House ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (64 ratings)
Rock Hall, Edesville, Maryland, United States
Balcony/Patio
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Vrbo
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Apartments and vacation rentals with a kitchen

Apartment  Bay View
$127 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.1
Very good (29 ratings)
Bay View, Norfolk, Virginia, United States
Kitchen
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Vrbo
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House  Olde Hampton
$251 per night
House ∙ 9 guests ∙ 3 bedrooms
4.7
Excellent (6 ratings)
Olde Hampton, Hampton, Virginia, United States
Kitchen
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Vrbo
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House  Annapolis
$258 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (6 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
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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 $86 per night.

Is it possible to find vacation rentals in Chesapeake Bay?

On tripping.com, you will find 8,587 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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