Find Vacation Rentals in Chesapeake

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Popular Chesapeake Vacation Rentals

Find the perfect Chesapeake vacation rental

House Western Branch South
from $450 per night
House ∙ 8 guests ∙ 4 bedrooms

222 m² House

5.0
Outstanding(1 rating)
Western Branch South, Chesapeake, Virginia, United States
HomeToGo
Details
House Western Branch North
from $187 per night
House ∙ 4 guests ∙ 2 bedrooms

92 m² House

4.8
Outstanding(5 ratings)
Western Branch North, Chesapeake, Virginia, United States
HomeToGo
Details
House South Norfolk
from $121 per night
5 guests ∙ 3 bedrooms

House

5.0
Outstanding(2 ratings)
South Norfolk, Chesapeake, Virginia, United States
Vrbo
Details
House Indian River
from $227 per night
House ∙ 6 guests ∙ 3 bedrooms

83 m² House

4.4
Very good(10 ratings)
Indian River, Chesapeake, Virginia, United States
Vrbo
Details
House Western Branch South
from $327 per night
9 guests ∙ 4 bedrooms

House

4.5
Excellent(14 ratings)
Western Branch South, Chesapeake, Virginia, United States
Vrbo
Details
House Chesapeake
from $376 per night
House ∙ 11 guests ∙ 6 bedrooms

186 m² House

5.0
Outstanding(11 ratings)
Chesapeake, Virginia, United States
Vrbo
Details
Farmhouse Pleasant Grove West
from $204 per night
Farmhouse ∙ 5 guests ∙ 1 bedroom

372 m² Farmhouse

4.8
Outstanding(10 ratings)
Pleasant Grove West, Chesapeake, Virginia, United States
Vrbo
Details
House Pleasant Grove West
from $129 per night
House ∙ 6 guests ∙ 3 bedrooms

121 m² House

5.0
Outstanding(23 ratings)
Pleasant Grove West, Chesapeake, Virginia, United States
Vrbo
Details
House Great Bridge
from $127 per night
3 guests ∙ 2 bedrooms

House

Great Bridge, Chesapeake, Virginia, United States
Vrbo
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Vacation rentals with Wi-Fi

House  Great Bridge
from $229 per night
5 guests ∙ 3 bedrooms

House

4.8
Outstanding(21 ratings)
Great Bridge, Chesapeake, Virginia, United States
Internet
Vrbo
Details
Condo  Indian River
from $240 per night
6 guests ∙ 2 bedrooms

Condo

Indian River, Chesapeake, Virginia, United States
Internet
Vrbo
Details
House  Deep Creek North
from $229 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(1 rating)
Deep Creek North, Chesapeake, Virginia, United States
Internet
Vrbo
Details
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Apartments and vacation rentals with a kitchen

Condo  Indian River
from $180 per night
4 guests ∙ 1 bedroom

Condo

Indian River, Chesapeake, Virginia, United States
Kitchen
HomeToGo
Details
Condo  Indian River
from $166 per night
2 guests ∙ 1 bedroom

Condo

Indian River, Chesapeake, Virginia, United States
Kitchen
HomeToGo
Details
Studio flat  Indian River
from $147 per night
3 guests ∙ 1 bedroom

Studio flat

Indian River, Chesapeake, Virginia, United States
Kitchen
HomeToGo
Details
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Vacation rentals and apartments with air conditioning

Apartment  Western Branch North
from $88 per night
2 guests ∙ 1 bedroom

Apartment

Western Branch North, Chesapeake, Virginia, United States
Air conditioning
Vrbo
Details
Cottage  Western Branch South
from $759 per night
Cottage ∙ 8 guests ∙ 4 bedrooms

222 m² Cottage

Western Branch South, Chesapeake, Virginia, United States
Air conditioning
HomeToGo
Details
House  Chesapeake
from $397 per night
4 guests ∙ 2 bedrooms

House

5.0
Outstanding(2 ratings)
Chesapeake, Virginia, United States
Air conditioning
Vrbo
Details
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Frequently Asked Questions

What is the price of vacation rentals in Chesapeake?

Usually, a stay in Chesapeake starts at $73 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 738 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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