Chesapeake vacation rentals

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Best Chesapeake vacation rentals

Most recommended vacation rentals in Chesapeake

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Good to know

Low season

October

High season

January

Average price (weeknight)

$147

Average price (weekend night)

$194
Cheapest month to stay with an average 46% drop in price.
Most expensive month to stay with an average 50% 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 is the most popular vacation rental property amenity in Chesapeake
  • Vacation rentals in Chesapeake are around 59% 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 King Guest Suite - A Togar Vacation Rental (9.6, 25 reviews), Econo Lodge Chesapeake Route 13 and I-464 (5.4, 203) and Econo Lodge Chesapeake Route 13 and I-464 (5.4, 203), based on ratings and reviews from real travelers.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Chesapeake for 17 days.
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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 $678.

  • 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 $2,904.

  • 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 agritourism, apartments, caravan parks, condos, cottages, houses, homestays, lodges and villas.

  • What are some of the most-loved vacation rentals available in Chesapeake?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Econo Lodge Little Creek.

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

    There are a number of dog and pet-friendly Chesapeake vacation rentals, with around 5% 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 $81. 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.

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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.

Chesapeake vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Chesapeake. Find cheap vacation homes to rent in Chesapeake. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Chesapeake that suits you best.

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