Chesapeake vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Chesapeake
Guests agree: these vacation rentals 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
Guest suite in Chesapeake
4.99 out of 5 average rating, 136 reviewsBeautiful Two Bedroom King Bed Guest House
Townhouse in Chesapeake
4.92 out of 5 average rating, 109 reviewsTasha's Townhouse *King, Queen, Twin*
Home in Virginia Beach
4.9 out of 5 average rating, 207 reviewsQuilted Quarters by the Bay with Private Entrance
Home in Norfolk
4.92 out of 5 average rating, 155 reviews@Whitβs End? Come in and Relax
Apartment in Williamsburg
4.84 out of 5 average rating, 361 reviewsThe Nook
Barn in Virginia Beach
4.79 out of 5 average rating, 831 reviewsCozy craftsman barn near the bay!
Cottage in Norfolk
5.0 out of 5 average rating, 250 reviewsBeautiful Cottage Waterfront Near Downtown Norfolk
Apartment in Virginia Beach
4.91 out of 5 average rating, 466 reviewsPrivate apartment only 3 blocks from the Beach
Other great vacation rentals in Chesapeake
Condo in Norfolk
4.79 out of 5 average rating, 155 reviewsBest Value Condo in Downtown Norfolk
Tiny home in Hampton
4.92 out of 5 average rating, 171 reviewsHampton River Retreat Tiny House
Guest suite in Virginia Beach
4.99 out of 5 average rating, 310 reviewsJust Steps Away to the Beach
Farm stay in Cape Charles
5.0 out of 5 average rating, 332 reviewsPrivate Guesthouse on Secluded Waterfront Farm
Guest suite in Virginia Beach
4.91 out of 5 average rating, 206 reviewsRest AβShore-Virginia Beach
Guest suite in Hampton
4.96 out of 5 average rating, 467 reviewsStorybook Cottage
Apartment in Portsmouth
4.96 out of 5 average rating, 241 reviewsCozy Ground Floor Apt in Historic Home
Guest suite in Norfolk
4.93 out of 5 average rating, 507 reviewsBeachfront Exclusive Bay front Suite
Quick stats about vacation rentals in Chesapeake
Total rentals
1.1K properties
Rentals with dedicated workspaces
590 properties have a dedicated workspace
Rentals with a pool
150 properties have a pool
Pet-friendly rentals
340 properties allow pets
Family-friendly rentals
510 properties are a good fit for families
Total number of reviews
31K reviews
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 550 vacation rentals in Olde Towne, over 110 vacation rentals in Salem, over 550 vacation rentals in Downtown Norfolk, and over 320 vacation rentals in Ghent.
Are there vacation rentals with a dedicated workspace in Chesapeake?
Yes! Work meets play with ease at over 590 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 340 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 150 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 130 house rentals with a bbq area in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chesapeake have a gym?
Absolutely! We offer over 60 house rentals with a gym in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do private suite rentals in Chesapeake have wifi?
Absolutely! We offer over 30 private suite rentals with wifi in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chesapeake have self check-in?
Absolutely! We offer over 160 house rentals with self check-in in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Chesapeake?
Chesapeake has more than 90 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Destinations to explore
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