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
Apartment in Newport News
4.97 out of 5 average rating, 148 reviewsCentrally Located Sleek Studio Apartment
Dec 3 – 10
Cottage in Norfolk
5.0 out of 5 average rating, 250 reviewsBeautiful Cottage Waterfront Near Downtown Norfolk
Sep 4 – 11
Townhouse in Chesapeake
4.92 out of 5 average rating, 109 reviewsTasha's Townhouse *King, Queen, Twin*
Aug 3 – 10
Guest suite in Carrollton
4.98 out of 5 average rating, 161 reviews2BR 1BA Spacious Guest Suite, Woods & Water Views
Sep 3 – 10
Guesthouse in Yorktown
4.97 out of 5 average rating, 203 reviewsCharming Yorktown Battlefield Cottage
Aug 12 – 19
Home in Norfolk
4.92 out of 5 average rating, 155 reviews@Whit’s End? Come in and Relax
Nov 8 – 15
Home in Smithfield
4.97 out of 5 average rating, 205 reviewsMason Manor - Downtown Smithfield next to WCP
Apr 17 – 24
Guest suite in Virginia Beach
4.85 out of 5 average rating, 173 reviewsSmall & Cozy Guest Suite w/ Private Bath & Jet-Tub
Jun 21 – 28
Other great vacation rentals in Chesapeake
Apartment in Virginia Beach
4.91 out of 5 average rating, 232 reviewsVB. Oceanfront/ Boardwalk,Beach, Pool, Balcony
Feb 4 – 11
Apartment in Portsmouth
4.84 out of 5 average rating, 300 reviewsSpacious 2 bedroom apt in Historic Port Norfolk
Oct 4 – 11
Tiny home in Hampton
4.92 out of 5 average rating, 171 reviewsHampton River Retreat Tiny House
Jan 17 – 24
Home in Norfolk
4.84 out of 5 average rating, 121 reviewsCozy Coastal Home
Dec 16 – 23
Farm stay in Cape Charles
5.0 out of 5 average rating, 332 reviewsPrivate Guesthouse on Secluded Waterfront Farm
Oct 20 – 27
Guest suite in Virginia Beach
4.99 out of 5 average rating, 310 reviewsJust Steps Away to the Beach
Jul 8 – 15
Apartment in Chesapeake
5.0 out of 5 average rating, 145 reviewsModern Luxury Peace & Quiet.
Sep 30 – Oct 7
Guesthouse in Coinjock
4.99 out of 5 average rating, 300 reviewsChurch's Island Carriage House
Jun 2 – 9
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.
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