Holiday rentals in Chesapeake
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Top-rated holiday rentals in Chesapeake
Guests agree: these stays are highly rated for location, cleanliness and more.
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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
Flat in Chesapeake
4.97 out of 5 average rating, 74 reviews1 King Master BR. β‘οΈFast Wifi. π Easy Self Check In
Guest favourite
Flat in Chesapeake
5.0 out of 5 average rating, 32 reviewsEntire Apartment - No Cleaning Fees!
Guest favourite
Townhouse in Chesapeake
4.97 out of 5 average rating, 33 reviewsCenter of Greenbrier
Guest favourite
Home in Chesapeake
4.88 out of 5 average rating, 25 reviewsChesapeake. 3 Bedroom 1-1/2 Bath Small family home
Guest favourite
Bungalow in Chesapeake
4.93 out of 5 average rating, 75 reviewsPrivate and Cozy Bungalow Loaded with Amenities
Guest favourite
Apartment in Chesapeake
5.0 out of 5 average rating, 5 reviews2BR Condo in Chesapeake - Western Branch
Guest favourite
Home in Norfolk
5.0 out of 5 average rating, 25 reviewsStylish Beach House, Hot Tub, Pet Friendly
Guest favourite
Home in Chesapeake
4.92 out of 5 average rating, 38 reviewsHidden Gem in Chesapeake, Virginia
Quick stats about holiday 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 BanksΒ Holiday rentals
- Virginia BeachΒ Holiday rentals
- RichmondΒ Holiday rentals
- NorfolkΒ Holiday rentals
- WilliamsburgΒ Holiday rentals
- Nags HeadΒ Holiday rentals
- Myrtle BeachΒ Holiday rentals
- WashingtonΒ Holiday rentals
- Deep Creek LakeΒ Holiday rentals
- PhiladelphiaΒ Holiday rentals
- New YorkΒ Holiday rentals
- Jersey CityΒ Holiday rentals
- Rentals with a hot tubΒ Chesapeake
- Family-friendly rentalsΒ Chesapeake
- Rentals with lake accessΒ Chesapeake
- Rentals with a cinemaΒ Chesapeake
- Private suite rentalsΒ Chesapeake
- Apartment rentalsΒ Chesapeake
- Rentals with poolsΒ Chesapeake
- Flat rentalsΒ Chesapeake
- Rentals with a fireplaceΒ Chesapeake
- Fitness-friendly rentalsΒ Chesapeake
- House rentalsΒ Chesapeake
- Rentals with beach accessΒ Chesapeake
- Rentals with a firepitΒ Chesapeake
- Smoking-friendly rentalsΒ Chesapeake
- Family-friendly rentalsΒ Chesapeake
- Rentals with a patioΒ Chesapeake
- Pet-friendly rentalsΒ Chesapeake
- Rentals with an EV chargerΒ Chesapeake
- Rentals with outdoor seatingΒ Chesapeake
- Monthly RentalsΒ Chesapeake
- Rentals with a washing machine and dryerΒ Chesapeake
- Rentals with breakfastΒ Chesapeake
- Waterfront rentalsΒ Chesapeake
- Townhouse rentalsΒ Chesapeake
- Yurt RentalsΒ United States
- Yurt RentalsΒ United Kingdom
- Castle RentalsΒ United States
- HouseboatsΒ United States
- Holiday CaravansΒ United Kingdom
- Private Island RentalsΒ United States
- Farm HousesΒ United States
- Farm CottagesΒ United Kingdom
- Cabin RentalsΒ Australia
- Luxury CabinsΒ United Kingdom
- Luxury CabinsΒ United States
- Holiday ChaletsΒ United Kingdom
- Cottage RentalsΒ United States
- Holiday CottagesΒ United Kingdom
- Mansion RentalsΒ United States
- Villa RentalsΒ United Kingdom
- Holiday BungalowsΒ United Kingdom
- Bungalow RentalsΒ United States
- Condo RentalsΒ United States
- Holiday ApartmentsΒ Australia
- Holiday HousesΒ United States
- Holiday HousesΒ United Kingdom
- Private Holiday RentalsΒ United Kingdom
- Big House RentalsΒ United States
- Big CottagesΒ Australia
- Large VillasΒ United Kingdom
- House Rentals with a PoolΒ United States
- Cabin Rentals with a PoolΒ United States
- Villas with a PoolΒ United Kingdom
- Apartments with a Hot TubΒ United States
- Holiday Cottages with a Hot TubΒ United Kingdom
- Beach CabinsΒ United States
- Beach CondosΒ United States
- Beachfront RentalsΒ United States
- Beach HousesΒ United Kingdom
- Beach VillasΒ United Kingdom
- Coastal CottagesΒ United Kingdom
- Pet-Friendly Vacation RentalsΒ United States
- Pet-Friendly Beach RentalsΒ United States
- Pet-Friendly Cabin RentalsΒ United States
- Dog-Friendly CottagesΒ United Kingdom
- Luxury Dog-Friendly CottagesΒ United Kingdom