Vacation Rentals in Chesapeake, Virginia

29 Properties Available

Spacious Chesapeake Home w/ Pool Table! Private vacation home
Spacious Chesapeake Home w/ Pool Table!
0 bd 0 ba Sleeps 0
$510 / night
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The Sparks Home! Relaxing Space + Lux Kitchen Private vacation home
The Sparks Home! Relaxing Space + Lux Kitchen
0 bd 0 ba Sleeps 0
$409 / night
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Townhome Newly renovated in GreatBridge, Chesapeake, ????? on another site Private vacation home
Townhome Newly renovated in GreatBridge, Chesapeake, ????? on another site
0 bd 0 ba Sleeps 0
$343 / night
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Beautifully appointed, spacious ranch style home located in Greenbrier! Private vacation home
Beautifully appointed, spacious ranch style home located in Greenbrier!
0 bd 0 ba Sleeps 0
$316 / night
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A Quiet Chesapeake Escape! Close to Rivers Casino! Private vacation home
A Quiet Chesapeake Escape! Close to Rivers Casino!
0 bd 0 ba Sleeps 0
$222 / night
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Bright Chesapeake Home Near Shopping & Dining Private vacation home
Bright Chesapeake Home Near Shopping & Dining
0 bd 0 ba Sleeps 0
$189 / night
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Holiday Inn Express Chesapeake - Norfolk, an IHG Hotel Hotel
Holiday Inn Express Chesapeake - Norfolk, an IHG Hotel
0 bd 0 ba Sleeps 0
$134 / night
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Courtyard by Marriott Chesapeake Hotel
Courtyard by Marriott Chesapeake
0 bd 0 ba Sleeps 0
$125 / night
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Landing at Hideaway at Greenbrier Luxury Apartment Homes - 1 Bedroom in Greenbrier East Apartment
Landing at Hideaway at Greenbrier Luxury Apartment Homes - 1 Bedroom in Greenbrier East
0 bd 0 ba Sleeps 0
$123 / night
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Delta Hotels by Marriott Chesapeake Norfolk Hotel
Delta Hotels by Marriott Chesapeake Norfolk
0 bd 0 ba Sleeps 0
$122 / night
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Fairfield Inn and Suites By Marriott Chesapeake Hotel
Fairfield Inn and Suites By Marriott Chesapeake
0 bd 0 ba Sleeps 0
$121 / night
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Hampton Inn Norfolk\/Chesapeake (Greenbrier Area) Hotel
Hampton Inn Norfolk\/Chesapeake (Greenbrier Area)
0 bd 0 ba Sleeps 0
$114 / night
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Hyatt Place Chesapeake Hotel
Hyatt Place Chesapeake
0 bd 0 ba Sleeps 0
$110 / night
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Comfort Suites Chesapeake - Norfolk Hotel
Comfort Suites Chesapeake - Norfolk
0 bd 0 ba Sleeps 0
$109 / night
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Aloft Chesapeake Hotel
Aloft Chesapeake
0 bd 0 ba Sleeps 0
$103 / night
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Hampton Inn & Suites Chesapeake-Battlefield Blvd. Hotel
Hampton Inn & Suites Chesapeake-Battlefield Blvd.
0 bd 0 ba Sleeps 0
$101 / night
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Econo Lodge Chesapeake Route 13 and I-464 Hotel
Econo Lodge Chesapeake Route 13 and I-464
0 bd 0 ba Sleeps 0
$100 / night
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Mainstay Suites Hotel
Mainstay Suites
0 bd 0 ba Sleeps 0
$94 / night
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Red Roof Inn Chesapeake Conference Center Hotel
Red Roof Inn Chesapeake Conference Center
0 bd 0 ba Sleeps 0
$89 / night
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Extended Stay America Suites Chesapeake Crossways Blvd Hotel
Extended Stay America Suites Chesapeake Crossways Blvd
0 bd 0 ba Sleeps 0
$88 / night
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Quality Inn Hotel
Quality Inn
0 bd 0 ba Sleeps 0
$65 / night
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Days Inn by Wyndham Chesapeake Motel
Days Inn by Wyndham Chesapeake
0 bd 0 ba Sleeps 0
$63 / night
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Economy 7 Inn - Chesapeake\/Portsmouth Hotel
Economy 7 Inn - Chesapeake\/Portsmouth
0 bd 0 ba Sleeps 0
$60 / night
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Budget Lodge Motel
Budget Lodge
0 bd 0 ba Sleeps 0
$59 / night
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Bowers Hill Inn Hotel
Bowers Hill Inn
0 bd 0 ba Sleeps 0
$55 / night
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Bright Chesapeake Home Near Shopping & Dining Cottage
Bright Chesapeake Home Near Shopping & Dining
0 bd 0 ba Sleeps 0
$0 / night
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Studios and Suites 4 Less Battlefield Blvd Motel
Studios and Suites 4 Less Battlefield Blvd
0 bd 0 ba Sleeps 0
$0 / night
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Studios and Suites 4 Less Gum Road Hotel
Studios and Suites 4 Less Gum Road
0 bd 0 ba Sleeps 0
$0 / night
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Studios and Suites 4 Less Western Branch Hotel
Studios and Suites 4 Less Western Branch
0 bd 0 ba Sleeps 0
$0 / night
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Why People Visit:

Chesapeake is a beautiful town located on the Virginia coast and is the perfect vacation spot for any fisherman, beachgoer, and history buff. Chesapeake has a little bit of everything for everyone to enjoy. So sit back relax and see what this historic town has to offer!

Chesapeake is located along the Atlantic Coast of Virginia, so there are no shortages of fish. Travelers come from all around to experience the deep sea Atlantic fishing with chances of catching all types of fish in the ocean. Not a fan of saltwater fish? That is okay! Chesapeake has multiple lakes within the vicinity full of different types of freshwater fish, from bass and catfish to bowfin and longnose gar, perfect for any type of fisherman.

Want to relax on a beach without a care in the world? Luckily for you, Chesapeake is located 20 miles away from the infamous Virginia Beach, the ideal location to bring your family and friends to relax on a historic spot where the colonists of Jamestown landed back in 1607.

Possibly the most attractive part of Chesapeake is the historic significance of the area which helped shape the American Revolution. In 1775 here stood the Battle of the Great Bridge where Patriots were able to defend the town from the invading British. The battle may have only lasted 5 minutes, but it forced the British to retreat out of the state of Virginia entirely. Today you can still witness this battle annually in December for a 2-day reenactment.

Once nightfall hits, head into the town to see exhilarating nightlife with plenty of live music and interesting events all year. There is never a dull moment in the Chesapeake nights.

Whatever outdoor adventure you are seeking, Chesapeake has it. Come out and explore the many different opportunities this town has to offer and stay in the luxury of a warm home by booking a vacation rental today!

Getting There and Getting Around:

There are two commercial airports located within an hour from Chesapeake: Norfolk International and Newport News/Williamsburg International Airport. If flying private, there are two other airports in the area that will supply fuel and other appliances you may need: Chesapeake Region and Hampton Road Executive Airport. Once landed the best way to get to your vacation rental and getting around town will be by bus, rideshare, train, or rental car.

What to Wear (The Weather):

The weather in Chesapeake is very pleasant throughout the year. With an average temperature of 78° F in the summertime and an average of 40° F in the winter time, there is no need to worry too much about being too warm or cold. Rainfall is quite common in the Virginia area so packing a raincoat and/or umbrella is recommended.

Accommodations:

A majority of the accommodations in the Santa Fe area are house rentals and have a lot to offer. The average house rental price is $400 per night and the average size is 2,000 sqft. If you are thinking about finding an apartment instead, there are plenty of those as well! The average price for an apartment rental is $250 per night and the average size is 1,000 sqft.