Holiday rentals in Chesapeake
Find and book unique accommodation on Airbnb
Top-rated holiday 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
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake holiday rentals
Other great holiday rentals in Chesapeake
Guest favourite
Guest suite in Virginia Beach
4.88 out of 5 average rating, 177 reviewsSmall & Cozy Guest Suite w/ Private Bath & Jet-Tub
Guest favourite
Guest house in Yorktown
4.97 out of 5 average rating, 206 reviewsCharming Yorktown Battlefield Cottage
Guest favourite
Townhouse in Chesapeake
4.92 out of 5 average rating, 111 reviewsTasha's Townhouse *King, Queen, Twin*
Guest favourite
Guest house in Portsmouth
4.97 out of 5 average rating, 151 reviewsSpring Hill Guest Cottage - Portsmouth
Guest favourite
Home in Smithfield
4.97 out of 5 average rating, 207 reviewsMason Manor - Downtown Smithfield next to WCP
Guest favourite
Home in Virginia Beach
4.9 out of 5 average rating, 211 reviewsQuilted Quarters by the Bay with Private Entrance
Guest favourite
Flat in Portsmouth
4.96 out of 5 average rating, 242 reviewsCozy Ground Floor Apt in Historic Home
Guest favourite
Flat in Williamsburg
4.84 out of 5 average rating, 363 reviewsThe Nook
Quick stats about holiday rentals in Chesapeake
Total rentals
1.1T 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
31T reviews
Destinations to explore
- Outer Banks Holiday rentals
- Virginia Beach Holiday rentals
- Richmond Holiday rentals
- Norfolk Holiday rentals
- Williamsburg Holiday rentals
- Nags Head Holiday rentals
- Myrtle Beach Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- Rentals with an EV charger Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with lake access Chesapeake
- Rentals with a cinema Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with a firepit Chesapeake
- Rentals with beach access Chesapeake
- Smoking-friendly rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with pools Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with a fireplace Chesapeake
- Townhouse rentals Chesapeake
- Apartment rentals Chesapeake
- Monthly Rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Flat rentals Chesapeake
- Waterfront rentals Chesapeake
- House 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