Chesapeake vacation rentals

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Best Chesapeake vacation rentals

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$58 - $252$252 - $445$445 - $639$639 - $832$832+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Chesapeake

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Welcome To Our Cozy Home In Chesapeake - Chesapeake - Bedroom
Welcome To Our Cozy Home In Chesapeake
Chesapeake, VA
9.6Wonderful(5)
House
$753+
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Gorgeous 1 Bedroom With Free Wifi & Street Parking - Chesapeake - Bedroom
Gorgeous 1 Bedroom With Free Wifi & Street Parking
Chesapeake, VA
Apartment
Free Wi-Fi
$118+
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Cute Guest House in Beautiful Wythe! Great Monthly! - Chesapeake - Bedroom
Cute Guest House in Beautiful Wythe! Great Monthly!
Chesapeake, VA
4.0Mediocre(1)
Apartment
$181+
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King Guest Suite - A Togar Vacation Rental - Chesapeake - Bedroom
King Guest Suite - A Togar Vacation Rental
Chesapeake, VA
9.7Wonderful(31)
Apartment
$105+
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The Full House - Chesapeake - Living room
The Full House
Chesapeake, VA
9.6Wonderful(5)
House
$142+
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Perfect Beach Getaway for 5! Steps to the Sand! - Chesapeake - Living room
Perfect Beach Getaway for 5! Steps to the Sand!
Chesapeake, VA
9.3Wonderful(23)
House
Free Wi-Fi
$268+
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Ultimate Vacation Home - Chesapeake - Building
Ultimate Vacation Home
Chesapeake, VA
House
$896+
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Country Escape Home in the Woods- Chesapeake, VA - Chesapeake - Living room
Country Escape Home in the Woods- Chesapeake, VA
Chesapeake, VA
10Wonderful(6)
House
$194+
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Newly Remodeled 2 Bedroom Duplex - Chesapeake - Kitchen
Newly Remodeled 2 Bedroom Duplex
Chesapeake, VA
House
$140+
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Bright Chesapeake Home Near Shopping and Dining - Chesapeake - Living room
Bright Chesapeake Home Near Shopping and Dining
Chesapeake, VA
9.6Wonderful(5)
House
Free Wi-Fi
Spa
$260+
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Cozy Private Backyard Apartment in Chesapeake - Chesapeake - Living room
Cozy Private Backyard Apartment in Chesapeake
Chesapeake, VA
Apartment
$131+
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The Sparks Home! Relaxing Space + Lux Kitchen - Chesapeake - Living room
The Sparks Home! Relaxing Space + Lux Kitchen
Chesapeake, VA
9.6Wonderful(5)
House
Free Wi-Fi
$479+
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Charming 3-bedroom bungalow with WiFi, AC in Chesapeake - Chesapeake - Living room
Charming 3-bedroom bungalow with WiFi, AC in Chesapeake
Chesapeake, VA
House
$514+
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Roomy and Cozy 3-bedroom home in Chesapeake near everything. - Chesapeake - Living room
Roomy and Cozy 3-bedroom home in Chesapeake near everything.
Chesapeake, VA
9.3Wonderful(9)
House
$282+
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King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near The Virginia Beach Business District! - Chesapeake - Pool
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near The Virginia Beach Business District!
Chesapeake, VA
10Wonderful(1)
Condo
Pool
$201+
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Dream Haven - 2BR/2BA - free parking on premises. - Chesapeake - Bedroom
Dream Haven - 2BR/2BA - free parking on premises.
Chesapeake, VA
Apartment
$128+
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
August
$391
$240
Cheapest month to stay with an average 79% drop in price.
Most expensive month to stay with an average 120% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Chesapeake vacation rental deals

  • Pet friendly and pool are the most popular vacation rental property amenities in Chesapeake
  • Vacation rentals in Chesapeake are around 72% more expensive than hotels on average. Search here to compare prices for all accommodation types in Chesapeake.
  • The best vacation rental properties in Chesapeake are 3-bedroom home away from home in fabulous Chesapeake, Virginia. (10.0, 29 reviews), King Guest Suite - A Togar Vacation Rental (9.7, 31), and Perfect Beach Getaway for 5! Steps to the Sand! (9.3, 23), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Chesapeake, you should consider visiting during the low season. The cheapest vacation homes in Chesapeake can be found in January and September.
  • The cheapest night for renting a vacation home in Chesapeake is Friday. In contrast, the most expensive is Tuesday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Chesapeake for 15 days.

FAQs when booking a vacation home in Chesapeake

  • How much is a vacation rental for a week in Chesapeake?

    The average price for a weekly Chesapeake vacation rental found by KAYAK users in the last 2 weeks is $1,833.

  • How much is a vacation rental for a month in Chesapeake?

    The average price for a monthly Chesapeake vacation rental found by KAYAK users in the last 2 weeks is $7,858.

  • What types of vacation rentals are available in Chesapeake?

    There are loads of different property types that you can make your vacation home in Chesapeake. You’ll find apartments, caravan parks, condos, cottages, houses, homestays, lodges and villas.

  • Are there any pet-friendly vacation rentals in Chesapeake?

    There are a number of dog and pet-friendly Chesapeake vacation rentals, with around 3% allowing you to bring your pet along with you.

  • How much is a vacation rental in Chesapeake for tonight?

    In the last 72 hours, users have found Chesapeake vacation rentals for tonight for as low as $385. Search here for similar prices

  • How can I find vacation rentals near me in Chesapeake?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Chesapeake?

Our map will help you find the perfect place to stay in Chesapeake by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Chesapeake