
Vacation rentals in Chesapeake
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Chesapeake
Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake vacation rentals
Other great vacation rentals in Chesapeake

R & R River House

Entire Apartment - No Cleaning Fees!

Blissful Nook @ Washington

Home Away From Home

Entire Cozy & Quiet 3BR/2BA Guest Suite

Beach Stay

Comfy House! The Perfect Getaway

Quiet 3/2 beautiful Chesapeake
Quick stats about vacation rentals in Chesapeake
Total rentals
870 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
32K reviews
Family-friendly rentals
400 properties are a good fit for families
Pet-friendly rentals
250 properties allow pets
Rentals with a pool
120 properties have a pool
Frequently Asked Questions
Where should I stay in Chesapeake?
Make yourself at home in Chesapeake by choosing from our most frequently booked neighborhoods. We have over 110 vacation rentals in Lynnhaven, over 110 vacation rentals in Salem, and over 50 vacation rentals in Great Bridge.
Are there vacation rentals with a dedicated workspace in Chesapeake?
Yes! Work meets play with ease at over 500 vacation rentals in Chesapeake featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chesapeake?
Four-legged friends are welcome in Chesapeake. Choose from more than 290 vacation rentals for guests traveling with pets.
Are there Chesapeake vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 140 vacation homes with pools in Chesapeake, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in hotel rentals in Chesapeake?
Experience the best of Chesapeake with our hotel rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chesapeake have a bbq area?
Absolutely! We offer over 110 house rentals with a bbq area in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Chesapeake have a gym?
Absolutely! We offer over 40 apartment rentals with a gym in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Chesapeake have wifi?
Absolutely! We offer over 30 condo rentals with wifi in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Chesapeake have self check-in?
Absolutely! We offer over 10 condo rentals with self check-in in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Chesapeake?
Chesapeake has more than 280 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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