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
Guest suite in Carrollton
4.98 out of 5 average rating, 162 reviews2BR 1BA Spacious Guest Suite, Woods & Water Views
Home in Smithfield
4.97 out of 5 average rating, 205 reviewsMason Manor - Downtown Smithfield next to WCP
Townhouse in Chesapeake
4.92 out of 5 average rating, 110 reviewsTasha's Townhouse *King, Queen, Twin*
Home in Virginia Beach
4.9 out of 5 average rating, 210 reviewsQuilted Quarters by the Bay with Private Entrance
Villa in Norfolk
4.94 out of 5 average rating, 138 reviews8 minutes walking from Sarah Constant Beach Park
Barn in Virginia Beach
4.8 out of 5 average rating, 835 reviewsCozy craftsman barn near the bay!
Guesthouse in Yorktown
4.97 out of 5 average rating, 203 reviewsCharming Yorktown Battlefield Cottage
Other great vacation rentals in Chesapeake
Tiny home in Hampton
4.92 out of 5 average rating, 171 reviewsHampton River Retreat Tiny House
Farm stay in Cape Charles
5.0 out of 5 average rating, 334 reviewsPrivate Guesthouse on Secluded Waterfront Farm
Cottage in Norfolk
4.98 out of 5 average rating, 177 reviewsPeaceful beach @Courtyard Cottage+No Cleaning Fee!
Apartment in Portsmouth
4.96 out of 5 average rating, 242 reviewsCozy Ground Floor Apt in Historic Home
Guest suite in Virginia Beach
4.97 out of 5 average rating, 238 reviewsScott's Garden Suite At The Crooked House
Guest suite in Virginia Beach
4.99 out of 5 average rating, 311 reviewsJust Steps Away to the Beach
Guest suite in Norfolk
4.93 out of 5 average rating, 219 reviewsCobblestone street apartment with rooftop views!
Apartment in Chesapeake
5.0 out of 5 average rating, 145 reviewsModern Luxury Peace & Quiet.
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 320 vacation rentals in Ghent, over 550 vacation rentals in Downtown Norfolk, 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 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 rv rentals in Chesapeake?
Experience the best of Chesapeake with our rv 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 120 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 guesthouse rentals in Chesapeake have wifi?
Absolutely! We offer over 20 guesthouse 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 townhouse rentals in Chesapeake?
Chesapeake has more than 70 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Destinations to explore
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- Rentals with a fire pit Chesapeake
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- Family-friendly rentals Chesapeake
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- Rentals with breakfast Chesapeake
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