Waterfront holiday rentals in Chesapeake
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Chesapeake
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for waterfront rentals in Chesapeake
Waterfront apartment rentals
Flat in Cape Charles
4.98 out of 5 average rating, 183 reviewsCape Charles Plantation Home βNevillβs Nook Suiteβ
Flat in Virginia Beach
4.94 out of 5 average rating, 208 reviewsTree Top Beach Bungalow 3 1/2 blocks fr beach
Flat in Yorktown
4.98 out of 5 average rating, 115 reviewsYorktown on the Waterfront
Flat in Chesapeake
4.91 out of 5 average rating, 11 reviewsSerene Tree House Retreat | Spacious 1br/1bth Home
Flat in Virginia Beach
5.0 out of 5 average rating, 17 reviewsSandbridge Beach Bay Getaway
Flat in Corolla
4.96 out of 5 average rating, 82 reviewsThe Coastal Studio
Flat in Virginia Beach
5.0 out of 5 average rating, 3 reviewsNEW Updated Oceanfront 2bd 2bth / Beachfront /Pool
Flat in Hampton
4.96 out of 5 average rating, 73 reviewsPenthouse Paradise On The Harbor
Waterfront house rentals
Home in Virginia Beach
4.99 out of 5 average rating, 168 reviewsPlay by the bay beach house,
Home in Norfolk
4.92 out of 5 average rating, 292 reviewsNew Beach Home on the Chesapeake Bay
Home in Norfolk
4.89 out of 5 average rating, 117 reviewsNew Renovation! Tons of Space + Dogs ok!
Home in Virginia Beach
4.83 out of 5 average rating, 107 reviewsStunning Views of Back Bay & Seconds to the Beach
Home in Portsmouth
4.97 out of 5 average rating, 39 reviewsPennyβs Palace 1 Bed/1 Bath Home
Home in Portsmouth
4.59 out of 5 average rating, 109 reviewsThe Mermaids Lair π§ββοΈ
Home in Knotts Island
4.94 out of 5 average rating, 86 reviewsIsland Lotus Yoga & Spa
Home in Norfolk
4.96 out of 5 average rating, 71 reviewsThe OV Beach Shack : cozy, fun beach house!
Waterfront apartment rentals
Apartment in Virginia Beach
4.88 out of 5 average rating, 180 reviewsOceanfront Gem VaB Studio Exceptional Views
Apartment in Williamsburg
4.94 out of 5 average rating, 105 reviewsLuxury Riverfront Condo w/ sunrise & sunset views
Apartment in Virginia Beach
4.93 out of 5 average rating, 161 reviewsTritonβs Treasure -3 Bedroom Condo on the Beach
Apartment in Virginia Beach
4.85 out of 5 average rating, 131 reviewsOceanfront Penthouse
Apartment in Virginia Beach
4.99 out of 5 average rating, 202 reviewsChic's Beach Rental and Fishing
Apartment in Virginia Beach
4.83 out of 5 average rating, 102 reviewsOceanfront, beachfront, boardwalk, fun, dolphins
Apartment in Virginia Beach
4.92 out of 5 average rating, 114 reviewsOcean & Bay Views - Local Family Owned & Operated
Apartment in Williamsburg
4.81 out of 5 average rating, 102 reviewsBook a Piece of History at Kingsmill Williamsburg
Quick stats about waterfront rentals in Chesapeake
Total rentals
100 properties
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
4.8K reviews
Nightly prices starting at
β¬Β 28 before taxes and fees
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
- Jersey CityΒ Holiday rentals
- New YorkΒ Holiday rentals
- Waterfront rentalsΒ United States
- Waterfront rentalsΒ Outer Banks
- Waterfront rentalsΒ Virginia Beach
- Waterfront rentalsΒ Virginia
- Rentals with a firepitΒ Chesapeake
- Rentals with a fireplaceΒ Chesapeake
- Rentals with poolsΒ Chesapeake
- Fitness-friendly rentalsΒ Chesapeake
- Private suite rentalsΒ Chesapeake
- Apartment rentalsΒ Chesapeake
- Family-friendly rentalsΒ Chesapeake
- Family-friendly rentalsΒ Chesapeake
- Rentals with a patioΒ Chesapeake
- Pet-friendly rentalsΒ Chesapeake
- Rentals with a cinemaΒ Chesapeake
- Rentals with lake accessΒ Chesapeake
- Rentals with a hot tubΒ Chesapeake
- Rentals with beach accessΒ Chesapeake
- Rentals with breakfastΒ Chesapeake
- House rentalsΒ Chesapeake
- Rentals with outdoor seatingΒ Chesapeake
- Rentals with an EV chargerΒ Chesapeake
- Smoking-friendly rentalsΒ Chesapeake
- Townhouse rentalsΒ Chesapeake
- Rentals with a washing machine and dryerΒ Chesapeake
- Flat rentalsΒ Chesapeake
- Monthly 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