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 Williamsburg
4.84 out of 5 average rating, 360 reviewsThe Nook
Nov 26 – Dec 3
Guesthouse in Yorktown
4.97 out of 5 average rating, 202 reviewsCharming Yorktown Battlefield Cottage
Jul 8 – 15
Home in Norfolk
4.92 out of 5 average rating, 153 reviews@Whit’s End? Come in and Relax
Jan 2 – 9
Cottage in Norfolk
5.0 out of 5 average rating, 249 reviewsBeautiful Cottage Waterfront Near Downtown Norfolk
Sep 19 – 26
Guesthouse in Portsmouth
4.97 out of 5 average rating, 151 reviewsSpring Hill Guest Cottage - Portsmouth
Mar 15 – 22
Guest suite in Carrollton
4.98 out of 5 average rating, 160 reviews2BR 1BA Spacious Guest Suite, Woods & Water Views
Sep 5 – 12
Apartment in Chesapeake
5.0 out of 5 average rating, 29 reviewsEntire Apartment - No Cleaning Fees!
Dec 3 – 10
Apartment in Chesapeake
4.95 out of 5 average rating, 41 reviewsBlissful Nook @ Washington
Aug 19 – 26
Other great vacation rentals in Chesapeake
Townhouse in Chesapeake
4.97 out of 5 average rating, 29 reviewsCenter of Greenbrier
Oct 1 – 8
Apartment in Chesapeake
4.94 out of 5 average rating, 17 reviewsCountry Escape - Next DOOR - Hidden Gem
Aug 10 – 17
Guesthouse in Suffolk
4.82 out of 5 average rating, 28 reviewsLakeside Retreat
Sep 22 – 29
Apartment in Suffolk
4.97 out of 5 average rating, 29 reviewsOne Bedroom Loft in Bridgeport, North Suffolk, VA
Feb 16 – 23
Apartment in Suffolk
5.0 out of 5 average rating, 70 reviewsCountry Living Guest House (Upstairs/Downstairs)
Feb 12 – 19
Townhouse in Virginia Beach
4.84 out of 5 average rating, 76 reviews3 bedroom townhome by Town Center
Feb 25 – Mar 4
Home in Hampton
4.92 out of 5 average rating, 12 reviewsTiny Blue Beach House
Dec 8 – 15
Apartment in Chesapeake
4.97 out of 5 average rating, 97 reviews2 BR With King. ⚡️Fast Wifi. 🔐 Easy Self Check-In.
Jun 13 – 20
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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- Monthly Rentals Chesapeake
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