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
Tiny home in Chesapeake
4.81 out of 5 average rating, 131 reviewsRural Tiny House in the Edge Of the Woods
Home in Virginia Beach
4.9 out of 5 average rating, 212 reviewsQuilted Quarters by the Bay with Private Entrance
Townhouse in Chesapeake
4.88 out of 5 average rating, 112 reviews2BR-1.5 Bath Electric & Vibrant R&R Townhome
Farm stay in Cape Charles
5.0 out of 5 average rating, 336 reviewsPrivate Guesthouse on Secluded Waterfront Farm
Guesthouse in Portsmouth
4.97 out of 5 average rating, 151 reviewsSpring Hill Guest Cottage - Portsmouth
Apartment in Newport News
4.97 out of 5 average rating, 151 reviewsCentrally Located Sleek Studio Apartment
Guest suite in Chesapeake
4.99 out of 5 average rating, 137 reviewsBeautiful Two Bedroom King Bed Guest House
Guesthouse in Hampton
4.99 out of 5 average rating, 293 reviewsSun Sea and Sand
Other great vacation rentals in Chesapeake
Guest suite in Virginia Beach
4.87 out of 5 average rating, 181 reviewsSmall & Cozy Guest Suite w/ Private Bath & Jet-Tub
Townhouse in Chesapeake
4.9 out of 5 average rating, 114 reviewsTasha's Townhouse *King, Queen, Twin*
Tiny home in Hampton
4.91 out of 5 average rating, 175 reviewsHampton River Retreat Tiny House
Home in Norfolk
4.85 out of 5 average rating, 124 reviewsCozy Coastal Home
Guest suite in Virginia Beach
4.99 out of 5 average rating, 312 reviewsJust Steps Away to the Beach
Guest suite in Virginia Beach
4.97 out of 5 average rating, 101 reviewsQuiet Suite with Private Entrance
Cottage in Norfolk
5.0 out of 5 average rating, 251 reviewsBeautiful Cottage Waterfront Near Downtown Norfolk
Cabin in Cape Charles
4.96 out of 5 average rating, 106 reviewsUltimate Cabin Farm Stay Cape Charles
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 550 vacation rentals in Downtown Norfolk, over 550 vacation rentals in Olde Towne, 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 apartment rentals in Chesapeake have a bbq area?
Absolutely! We offer over 10 apartment 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 apartment rentals in Chesapeake have wifi?
Absolutely! We offer over 210 apartment 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 condo rentals in Chesapeake?
Chesapeake has more than 10 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Destinations to explore
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- Rentals with a hot tub Chesapeake
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- Kid-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a home theater Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with pools Chesapeake
- Rentals with breakfast Chesapeake
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