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.

Choose the perfect vacation rental
Best Vacation Home Deals in Chesapeake
Find a vacation rental fitting your expectations among the 647 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 71%!
Top-Rated Rentals and Accommodations in Chesapeake
Recommended Vacation Rentals in Chesapeake
Find your perfect vacation rental in Chesapeake: from $66 per night
Budget-friendly Vacation Rentals in Chesapeake
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 with Wi-Fi
Stay connected while traveling and book a Chesapeake accommodation with high-speed internet.
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 8, 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.
Waterfront Vacation Rentals in Chesapeake
Want to find an incredible beachfront rental in Chesapeake?
Try out the 'distance to water' filter during your search and see only the best beach houses for your vacation. You can choose from a number of home rentals in Chesapeake that are located within walking distance from the coast. From dog-friendly rentals by the beach to waterfront cabins with pools, the perfect accommodation in Chesapeake is out there - discover it now via HomeToGo.

7-Day Weather Forecast in Chesapeake
Information about vacation rentals in Chesapeake
🏡 Vacation rentals | 647 properties |
---|---|
💳 Possible discounts | up to 71% |
🌙 Nightly prices starting at | $66 |
⭐ Popular amenities | Internet, TV and Air conditioning |
🐾 Pet friendly accommodations | 68 properties |
🏊 Vacation rentals with pools | 344 properties |
Frequently Asked Questions
What is the nightly price for a vacation rental in Chesapeake?
The average accommodation in Chesapeake is priced at $66 per night. If you would like to stay in a house rental, the average price is $376 per night. A apartment rental Chesapeake will cost $214 per night on average.
How many vacation homes are available for booking in Chesapeake?
There are 647 rentals in Chesapeake to browse and book for your next trip.
What amenities are most popular for vacation rentals in Chesapeake?
Usually travelers search for TV, Internet, and Air conditioning when booking a vacation rental in Chesapeake.
How many vacation homes with a pool are in Chesapeake?
Browse 344 vacation rentals available in Chesapeake.
Are dogs allowed in vacation rentals in Chesapeake?
Absolutely, currently there are 68 rentals in Chesapeake that allow pets , with an average nightly rate of $219.
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