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
Guesthouse in Yorktown
4.97 out of 5 average rating, 211 reviewsCharming Yorktown Battlefield Cottage
Guesthouse in Portsmouth
4.97 out of 5 average rating, 154 reviewsSpring Hill Guest Cottage - Portsmouth
Apartment in Newport News
4.97 out of 5 average rating, 154 reviewsCentrally Located Sleek Studio Apartment
Cottage in Norfolk
4.97 out of 5 average rating, 275 reviewsLovely Ocean View Cottage
Home in Smithfield
4.97 out of 5 average rating, 212 reviewsMason Manor - Downtown Smithfield next to WCP
Cottage in Norfolk
4.98 out of 5 average rating, 182 reviewsPeaceful beach @Courtyard Cottage+No Cleaning Fee!
Apartment in Portsmouth
4.96 out of 5 average rating, 245 reviewsCozy Ground Floor Apt in Historic Home
Home in Virginia Beach
4.92 out of 5 average rating, 265 reviewsMaster bedroom suite 3 blocks from the beach
Other great vacation rentals in Chesapeake
Apartment in Chesapeake
4.96 out of 5 average rating, 102 reviews2 BR With King. ⚡️Fast Wifi. 🔐 Easy Self Check-In.
Tiny home in Hampton
4.91 out of 5 average rating, 178 reviewsHampton River Retreat Tiny House
Condo in Norfolk
4.8 out of 5 average rating, 161 reviewsBest Value Condo in Downtown Norfolk
Guest suite in Carrollton
4.98 out of 5 average rating, 166 reviews2BR 1BA Spacious Guest Suite, Woods & Water Views
Cottage in Virginia Beach
4.95 out of 5 average rating, 313 reviewsSeaglass Cottage
Cabin in Cape Charles
4.96 out of 5 average rating, 110 reviewsUltimate Cabin Farm Stay Cape Charles
Guest suite in Virginia Beach
4.99 out of 5 average rating, 314 reviewsJust Steps Away to the Beach
Guest suite in Virginia Beach
4.89 out of 5 average rating, 561 reviewsQuiet Neighborhood 7 Miles From the Beaches
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 110 vacation rentals in Salem, over 550 vacation rentals in Downtown Norfolk, over 550 vacation rentals in Olde Towne, 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 private suite rentals in Chesapeake?
Experience the best of Chesapeake with our private suite rentals, starting at about $30 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 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 apartment rentals in Chesapeake have self check-in?
Absolutely! We offer over 50 apartment 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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- Monthly Rentals Chesapeake
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