Find Vacation Rentals in Chesapeake Bay

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Popular Chesapeake Bay Vacation Rentals

Find the perfect Chesapeake Bay vacation rental

House Deale
from $290 per night
House ∙ 8 guests ∙ 4 bedrooms

177 m² House

4.9
Outstanding(139 ratings)
Deale, Anne Arundel County, Maryland, United States
Details
House Deale
from $449 per night
10 guests ∙ 3 bedrooms

House

5.0
Outstanding(26 ratings)
Deale, Anne Arundel County, Maryland, United States
Details
House Fox Hill - Grandview
from $625 per night
House ∙ 12 guests ∙ 4 bedrooms

313 m² House

4.5
Excellent(48 ratings)
Fox Hill - Grandview, Hampton, Virginia, United States
Details
House Arnold
from $1,135 per night
14 guests ∙ 6 bedrooms

House

5.0
Outstanding(1 rating)
Arnold, Anne Arundel County, Maryland, United States
Details
House Churchton
from $857 per night
13 guests ∙ 6 bedrooms

House

4.6
Excellent(19 ratings)
Churchton, Deale, Maryland, United States
Details
House Deale
from $424 per night
8 guests ∙ 3 bedrooms

House

5.0
Outstanding(96 ratings)
Deale, Anne Arundel County, Maryland, United States
Details
House Stevensville
from $256 per night
8 guests ∙ 4 bedrooms

House

5.0
Outstanding(4 ratings)
Stevensville, Kent Island, Maryland, United States
Details
House Port Haywood
from $239 per night
House ∙ 8 guests ∙ 4 bedrooms

214 m² House

5.0
Outstanding(160 ratings)
Port Haywood, Chesapeake, Virginia, United States
Details
House Buckroe Beach
from $225 per night
House ∙ 10 guests ∙ 3 bedrooms

167 m² House

4.8
Outstanding(60 ratings)
Buckroe Beach, Hampton, Virginia, United States
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Vacation rentals with Wi-Fi

House  Cape Charles
from $436 per night
House ∙ 15 guests ∙ 5 bedrooms

297 m² House

4.5
Excellent(59 ratings)
Cape Charles, Northampton County, Virginia, United States
Internet
Details
House  Reedville
from $221 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(6 ratings)
Reedville, Northumberland County, Virginia, United States
Internet
Details
House  Cambridge
from $714 per night
House ∙ 16 guests ∙ 5 bedrooms

367 m² House

5.0
Outstanding(60 ratings)
Cambridge, Dorchester County, Maryland, United States
Internet
Details
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Vacation rentals and apartments with air conditioning

House  Chesapeake Ranch Estates-Drum Point
from $417 per night
House ∙ 8 guests ∙ 6 bedrooms

223 m² House

4.6
Excellent(10 ratings)
Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
Air conditioning
Details
House  Ridge
from $493 per night
8 guests ∙ 4 bedrooms

House

5.0
Outstanding(79 ratings)
Ridge, St. Inigoes, Maryland, United States
Air conditioning
Details
House  Kilmarnock
from $686 per night
16 guests ∙ 6 bedrooms

House

5.0
Outstanding(25 ratings)
Kilmarnock, Lancaster County, Virginia, United States
Air conditioning
Details
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Apartments and vacation rentals with a kitchen

House  Oakmont
from $150 per night
House ∙ 5 guests ∙ 3 bedrooms

106 m² House

Oakmont, Norfolk, Virginia, United States
Kitchen
Details
House  Annapolis
from $991 per night
House ∙ 10 guests ∙ 5 bedrooms

311 m² House

5.0
Outstanding(66 ratings)
Annapolis, Anne Arundel County, Maryland, United States
Kitchen
Details
House  Cape Charles
from $1,120 per night
16 guests ∙ 6 bedrooms

House

5.0
Outstanding(3 ratings)
Cape Charles, Northampton County, Virginia, United States
Kitchen
Details
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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 $89 per night.

Is it possible to find vacation rentals in Chesapeake Bay?

On tripping.com, you will find 10,232 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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