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
Home in Smithfield
4.97 out of 5 average rating, 209 reviewsMason Manor - Downtown Smithfield next to WCP
Home in Norfolk
4.92 out of 5 average rating, 159 reviews@Whit’s End? Come in and Relax
Guesthouse in Portsmouth
4.97 out of 5 average rating, 153 reviewsSpring Hill Guest Cottage - Portsmouth
Guest suite in Virginia Beach
4.97 out of 5 average rating, 243 reviewsScott's Garden Suite At The Crooked House
Cottage in Norfolk
5.0 out of 5 average rating, 251 reviewsBeautiful Cottage Waterfront Near Downtown Norfolk
Guesthouse in Yorktown
4.97 out of 5 average rating, 208 reviewsCharming Yorktown Battlefield Cottage
Home in Virginia Beach
4.92 out of 5 average rating, 264 reviewsMaster bedroom suite 3 blocks from the beach
Apartment in Newport News
4.97 out of 5 average rating, 152 reviewsCentrally Located Sleek Studio Apartment
Other great vacation rentals in Chesapeake
Guest suite in Carrollton
4.98 out of 5 average rating, 164 reviews2BR 1BA Spacious Guest Suite, Woods & Water Views
Townhouse in Chesapeake
4.91 out of 5 average rating, 116 reviewsTasha's Townhouse *King, Queen, Twin*
Guest suite in Virginia Beach
4.91 out of 5 average rating, 208 reviewsRest A’Shore-Virginia Beach
Apartment in Portsmouth
4.96 out of 5 average rating, 243 reviewsCozy Ground Floor Apt in Historic Home
Tiny home in Hampton
4.91 out of 5 average rating, 176 reviewsHampton River Retreat Tiny House
Guesthouse in Hampton
4.99 out of 5 average rating, 293 reviewsSun Sea and Sand
Home in Virginia Beach
4.9 out of 5 average rating, 213 reviewsQuilted Quarters by the Bay with Private Entrance
Guest suite in Virginia Beach
4.99 out of 5 average rating, 313 reviewsJust Steps Away to the Beach
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 320 vacation rentals in Ghent, over 110 vacation rentals in Salem, over 550 vacation rentals in Olde Towne, and over 550 vacation rentals in Downtown Norfolk.
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 apartment rentals in Chesapeake?
Experience the best of Chesapeake with our apartment rentals, starting at about $10 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 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 40 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 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.
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