Vacation rentals in Chesapeake
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Chesapeake
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
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
Guest favourite
Guest suite in Virginia Beach
4.87 out of 5 average rating, 172 reviewsSmall & Cozy Guest Suite w/ Private Bath & Jet-Tub
Jun. 21 – 28
$190 CAD per night
Guest favourite
Townhouse in Chesapeake
4.92 out of 5 average rating, 109 reviewsTasha's Townhouse *King, Queen, Twin*
Aug. 18 – 25
$348 CAD per night
Guest favourite
Barn in Virginia Beach
4.79 out of 5 average rating, 832 reviewsCozy craftsman barn near the bay!
Nov. 22 – 29
$154 CAD per night
Guest favourite
Apartment in Williamsburg
4.84 out of 5 average rating, 361 reviewsThe Nook
Nov. 12 – 19
$167 CAD per night
Guest favourite
Home in Smithfield
4.97 out of 5 average rating, 205 reviewsMason Manor - Downtown Smithfield next to WCP
Dec. 23 – 30
$181 CAD per night
Guest favourite
Guest suite in Carrollton
4.98 out of 5 average rating, 161 reviews2BR 1BA Spacious Guest Suite, Woods & Water Views
Jan. 19 – 26
$172 CAD per night
Guest favourite
Home in Virginia Beach
4.9 out of 5 average rating, 209 reviewsQuilted Quarters by the Bay with Private Entrance
Dec. 4 – 11
$140 CAD per night
Guest favourite
Home in Norfolk
4.92 out of 5 average rating, 155 reviews@Whit’s End? Come in and Relax
Dec. 6 – 13
$168 CAD per night
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
Destinations to explore
- Outer Banks Vacation rentals
- Virginia Beach Vacation rentals
- Richmond Vacation rentals
- Norfolk Vacation rentals
- Williamsburg Vacation rentals
- Nags Head Vacation rentals
- Myrtle Beach Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- Smoking-friendly rentals Chesapeake
- House rentals Chesapeake
- Waterfront rentals Chesapeake
- Rentals with a patio Chesapeake
- Rentals with lake access Chesapeake
- Rentals with an EV charger Chesapeake
- Monthly Rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a firepit Chesapeake
- Fitness-friendly rentals Chesapeake
- Condo rentals Chesapeake
- Kid-friendly rentals Chesapeake
- Rentals with beach access Chesapeake
- Rentals with breakfast Chesapeake
- Apartment rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with pools Chesapeake
- Rentals with a home theater Chesapeake
- Rentals with a washer and dryer Chesapeake
- Pet-friendly rentals Chesapeake
- Townhouse rentals Chesapeake
- Private suite rentals Chesapeake
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom