
Vacation rentals in Chesapeake
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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

Serene Tree House Retreat | Spacious 1br/1bth Home

Historic Hideaway Private Apartment/Suite

Entire Apartment - No Cleaning Fees!

Blissful Nook @ Washington

Quiet Neighborhood 7 Miles From the Beaches

Cook's Country Escape - House nestled in woods

Comfy House! The Perfect Getaway

Panoramic river view retreat
Quick stats about vacation rentals in Chesapeake
Total rentals
970 properties
Total number of reviews
32K reviews
Family-friendly rentals
440 properties are a good fit for families
Pet-friendly rentals
280 properties allow pets
Rentals with a pool
130 properties have a pool
Rentals with dedicated workspaces
510 properties have a dedicated workspace
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 480 vacation rentals in Olde Towne, over 480 vacation rentals in Downtown Norfolk, over 50 vacation rentals in Great Bridge, and over 110 vacation rentals in Salem.
Are there vacation rentals with a dedicated workspace in Chesapeake?
Yes! Work meets play with ease at over 510 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 280 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 130 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 condo rentals in Chesapeake?
Experience the best of Chesapeake with our condo rentals, starting at about $50 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 townhouse rentals in Chesapeake have a gym?
Absolutely! We offer over 10 townhouse 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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