Located along the Intracoastal Waterway on Virginia’s Atlantic coast, Chesapeake boasts a host of other extensive waterways ranging from lakes to rivers and canals. Relax in a charming house rental, or one of the city's many condo rentals, and experience numerous outdoor activities such as birdwatching and hiking. If you choose to stay in the city, museums and diverse dining options abound.

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Best Vacation Home Deals in Chesapeake
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Find a vacation rental fitting your expectations among the 638 great accommodations from numerous providers in Chesapeake. HomeToGo, a vacation rental search engine, instantly compares all of these offers so you can save up to 46%!
Top-Rated Rentals and Accommodations in Chesapeake
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Recommended Vacation Rentals in Chesapeake
Find your perfect vacation rental in Chesapeake: from $66 per night
Budget-friendly Vacation Rentals in Chesapeake
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Vacation rentals with Wi-Fi
Stay connected while traveling and book a Chesapeake accommodation with high-speed internet.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Chesapeake rental with full kitchen.
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Chesapeake and book a vacation rental with air conditioning.
Popular Rental Amenities in Chesapeake
Nearly half of the rentals offer a pool, which makes Chesapeake an excellent vacation destination for people looking to spend vacation poolside. Additionally, more House rental have pools than any other property type. They are an excellent choice if you go in a group of 11, as that is the number of people they can usually accommodate. If you would also like to be close to the water, a few of the rentals providing a pool are located within 2 miles of the waterfront.
7-Day Weather Forecast in Chesapeake
Information about vacation rentals in Chesapeake
🏡 Vacation rentals available | 629 homes |
---|---|
💳 Possible discounts | up to 56% |
🌙 Nightly prices starting at | $66 |
⭐ Popular amenities | Pets allowed, Pool and Internet |
🐾 Pet friendly homes | 63 homes |
🏊 Vacation rentals with pools | 285 homes |
Frequently Asked Questions
What is the price per night for a vacation home in Chesapeake?
The nightly price of accommodations in Chesapeake starts at $66. If you’re interested in a house rental, the average price is $383 per night. A apartment rental Chesapeake will cost $183 per night on average.
How many vacation homes are available for booking in Chesapeake?
Currently there are 629 vacation rentals in Chesapeake to browse and book for your trip.
What amenities are most popular for vacation homes in Chesapeake?
If you're looking to book a vacation rental in Chesapeake, the most common amenities are: Pool, Pets allowed and Internet.
How many vacation rentals with pools are there in Chesapeake?
Chesapeake offers 285 Hotel room and Condo options available for booking.
Are pets allowed in vacation rentals in Chesapeake?
Absolutely, there are 63 vacation rentals in Chesapeake that allow dogs , with an average nightly rate of $215.
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