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, 203 reviewsCharming Yorktown Battlefield Cottage
Sep 25 – Oct 2
Home in Norfolk
4.92 out of 5 average rating, 153 reviews@Whit’s End? Come in and Relax
Jan 14 – 21
Apartment in Williamsburg
4.84 out of 5 average rating, 360 reviewsThe Nook
Nov 23 – 30
Guesthouse in Portsmouth
4.97 out of 5 average rating, 151 reviewsSpring Hill Guest Cottage - Portsmouth
Aug 14 – 21
Apartment in Virginia Beach
4.9 out of 5 average rating, 186 reviewsVB Oceanfront Studio Balcony,Beach,Boardwalk, Pool
Jan 12 – 19
Guest suite in Virginia Beach
4.99 out of 5 average rating, 309 reviewsJust Steps Away to the Beach
Jul 21 – 28
Townhouse in Chesapeake
4.92 out of 5 average rating, 107 reviewsTasha's Townhouse *King, Queen, Twin*
Jul 14 – 21
Apartment in Chesapeake
4.9 out of 5 average rating, 21 reviewsWarm Luxury unit Central Greenbrier
May 26 – Jun 2
Other great vacation rentals in Chesapeake
Townhouse in Chesapeake
4.97 out of 5 average rating, 29 reviewsCenter of Greenbrier
Aug 29 – Sep 5
Apartment in Chesapeake
4.94 out of 5 average rating, 17 reviewsCountry Escape - Next DOOR - Hidden Gem
Aug 10 – 17
Apartment in Chesapeake
4.97 out of 5 average rating, 72 reviews1 King Master BR. ⚡️Fast Wifi. 🔐 Easy Self Check In
Jun 9 – 16
Guesthouse in Suffolk
4.82 out of 5 average rating, 28 reviewsLakeside Retreat
May 17 – 24
Apartment in Suffolk
4.97 out of 5 average rating, 29 reviewsOne Bedroom Loft in Bridgeport, North Suffolk, VA
Sep 1 – 8
Apartment in Suffolk
5.0 out of 5 average rating, 70 reviewsCountry Living Guest House (Upstairs/Downstairs)
Jun 23 – 30
Townhouse in Virginia Beach
4.84 out of 5 average rating, 76 reviews3 bedroom townhome by Town Center
Feb 25 – Mar 4
Home in Chesapeake
4.92 out of 5 average rating, 38 reviewsHidden Gem in Chesapeake, Virginia
Oct 21 – 28
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 320 vacation rentals in Ghent, over 550 vacation rentals in Downtown Norfolk, and over 550 vacation rentals in Olde Towne.
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 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 apartment rentals in Chesapeake have a gym?
Absolutely! We offer over 70 apartment 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 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 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.
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- Apartment rentals Chesapeake
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