Find Vacation Rentals in Chesapeake

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Chesapeake
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Popular Chesapeake Vacation Rentals

Find the perfect Chesapeake vacation rental

House Western Branch North
$161 per night
House ∙ 4 guests ∙ 2 bedrooms
Western Branch North, Chesapeake, Virginia, United States
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Vrbo
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House Pleasant Grove West
$132 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (1 rating)
Pleasant Grove West, Chesapeake, Virginia, United States
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Vrbo
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House Greenbrier West
$108 per night
House ∙ 5 guests ∙ 3 bedrooms
Greenbrier West, Chesapeake, Virginia, United States
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Vrbo
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Apartment Indian River
$253 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Indian River, Chesapeake, Virginia, United States
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Vrbo
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House South Norfolk
$133 per night
House ∙ 5 guests ∙ 3 bedrooms
South Norfolk, Chesapeake, Virginia, United States
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Vrbo
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House Western Branch North
$149 per night
House ∙ 6 guests ∙ 3 bedrooms
Western Branch North, Chesapeake, Virginia, United States
Details
Vrbo
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House South Norfolk
$279 per night
House ∙ 8 guests ∙ 4 bedrooms
South Norfolk, Chesapeake, Virginia, United States
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Vrbo
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House Western Branch South
$253 per night
House ∙ 9 guests ∙ 4 bedrooms
Western Branch South, Chesapeake, Virginia, United States
Details
Expedia
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House Indian River
$115 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (2 ratings)
Indian River, Chesapeake, Virginia, United States
Details
Vrbo
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Vacation rentals with Wi-Fi

Condo Internet Indian River
$381 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.7
"Outstanding" (11 ratings)
Indian River, Chesapeake, Virginia, United States
Internet
Details
Vrbo
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Apartment Internet South Norfolk
$108 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Norfolk, Chesapeake, Virginia, United States
Internet
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Vrbo
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Apartment Internet Indian River
$252 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Indian River, Chesapeake, Virginia, United States
Internet
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Vrbo
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Apartments and vacation rentals with a kitchen

Condo Kitchen Greenbrier West
$299 per night
Condo ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (4 ratings)
Greenbrier West, Chesapeake, Virginia, United States
Kitchen
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Vrbo
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House Kitchen Indian River
$344 per night
House ∙ 4 guests ∙ 3 bedrooms
4.8
"Excellent" (8 ratings)
Indian River, Chesapeake, Virginia, United States
Kitchen
Details
Vrbo
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Apartment Kitchen Greenbrier West
$128 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Greenbrier West, Chesapeake, Virginia, United States
Kitchen
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Vrbo
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Vacation rentals and apartments with air conditioning

House Aircondition Chesapeake
$392 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (2 ratings)
Chesapeake, Virginia, United States
Aircondition
Details
Vrbo
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House Aircondition Pleasant Grove West
$125 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (1 rating)
Pleasant Grove West, Chesapeake, Virginia, United States
Aircondition
Details
Expedia
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Apartment Aircondition Indian River
$252 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Indian River, Chesapeake, Virginia, United States
Aircondition
Details
Vrbo
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Frequently Asked Questions

What is the price of vacation rentals in Chesapeake?

Usually, a stay in Chesapeake starts at $66 per night.

Is there a wide selection of vacation rentals in Chesapeake?

Our large collection of vacation homes makes it easy to filter and compare 626 offers in Chesapeake.

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

Find the best Chesapeake vacation rentals on Tripping.com. With over 105 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Chesapeake range from $29 a night. Many rentals can also be booked directly online. Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 58 homes in Chesapeake offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 42 rentals with pool or jacuzzi, or relax with the family in one of the 49 homes with cable TV. For all those pet owners with dogs or cats, Chesapeake offers 35 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com. Search properties from 6 vacation rental sites in Chesapeake where the top providers in that area are HRS Holidays, Booking.com, and Agoda. There are 44 HRS Holidays rentals, 22 Booking.com short term rentals and 22 Agoda vacation rentals.

Popular Day Trips Near Chesapeake

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