Find Vacation Rentals in Chesapeake

We have 641 properties to choose from
Chesapeake
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Chesapeake
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Popular Chesapeake Vacation Rentals

Find the perfect Chesapeake vacation rental

House Western Branch North
$199 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (2 ratings)
Western Branch North, Chesapeake, Virginia, United States
Details
Vrbo
Details
Details
House Great Bridge
$103 per night
House ∙ 3 guests ∙ 2 bedrooms
Great Bridge, Chesapeake, Virginia, United States
Details
Vrbo
Details
Details
House Western Branch South
$292 per night
House ∙ 8 guests ∙ 4 bedrooms
4.5
Excellent (7 ratings)
Western Branch South, Chesapeake, Virginia, United States
Details
Vrbo
Details
Details
House Western Branch North
$207 per night
House ∙ 6 guests ∙ 3 bedrooms
4.5
Excellent (12 ratings)
Western Branch North, Chesapeake, Virginia, United States
Details
Vrbo
Details
Details
House Western Branch North
$209 per night
House ∙ 4 guests ∙ 2 bedrooms
4.5
Excellent (2 ratings)
Western Branch North, Chesapeake, Virginia, United States
Details
Vrbo
Details
Details
House Chesapeake
$322 per night
House ∙ 11 guests ∙ 4 bedrooms
5.0
Outstanding (6 ratings)
Chesapeake, Virginia, United States
Details
Vrbo
Details
Details
House Greenbrier West
$151 per night
House ∙ 5 guests ∙ 3 bedrooms
4.7
Excellent (6 ratings)
Greenbrier West, Chesapeake, Virginia, United States
Details
Vrbo
Details
Details
House Western Branch North
$182 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (7 ratings)
Western Branch North, Chesapeake, Virginia, United States
Details
Vrbo
Details
Details
House Pleasant Grove West
$169 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (19 ratings)
Pleasant Grove West, Chesapeake, Virginia, United States
Details
Vrbo
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Vacation Homes With Terraces

House  Western Branch North
$181 per night
House ∙ 4 guests ∙ 2 bedrooms
4.5
Excellent (2 ratings)
Western Branch North, Chesapeake, Virginia, United States
Balcony/Patio
Details
HomeToGo
Details
Details
House  Greenbrier West
$740 per night
House ∙ 10 guests ∙ 4 bedrooms
Greenbrier West, Chesapeake, Virginia, United States
Balcony/Patio
Details
Vrbo
Details
Details
Apartment  Deep Creek South
$88 per night
Apartment ∙ 3 guests ∙ 1 bedroom
5.0
Outstanding (54 ratings)
Deep Creek South, Chesapeake, Virginia, United States
Balcony/Patio
Details
Vrbo
Details
Details
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Vacation rentals with Wi-Fi

House  Western Branch North
$255 per night
House ∙ 8 guests ∙ 4 bedrooms
Western Branch North, Chesapeake, Virginia, United States
Internet
Details
HomeToGo
Details
Details
House  Greenbrier West
$242 per night
House ∙ 5 guests ∙ 2 bedrooms
Greenbrier West, Chesapeake, Virginia, United States
Internet
Details
Vrbo
Details
Details
House  Indian River
$231 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (2 ratings)
Indian River, Chesapeake, Virginia, United States
Internet
Details
Vrbo
Details
Details
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Vacation rentals and apartments with air conditioning

Studio flat  Indian River
$178 per night
Studio flat ∙ 3 guests ∙ 1 bedroom
Indian River, Chesapeake, Virginia, United States
Air conditioning
Details
HomeToGo
Details
Details
House  Great Bridge
$227 per night
House ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding (3 ratings)
Great Bridge, Chesapeake, Virginia, United States
Air conditioning
Details
Vrbo
Details
Details
House  Western Branch North
$286 per night
House ∙ 8 guests ∙ 4 bedrooms
4.0
Very good (6 ratings)
Western Branch North, Chesapeake, Virginia, United States
Air conditioning
Details
Vrbo
Details
Details
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Frequently Asked Questions

What is the price of vacation rentals in Chesapeake?

Usually, a stay in Chesapeake starts at $65 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 746 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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