Waterfront vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake waterfront rentals
Waterfront apartment rentals
Apartment in Virginia Beach
4.94 out of 5 average rating, 208 reviewsTree Top Beach Bungalow 3 1/2 blocks fr beach
Apartment in Yorktown
4.98 out of 5 average rating, 115 reviewsYorktown on the Waterfront
Apartment in Chesapeake
4.91 out of 5 average rating, 11 reviewsSerene Tree House Retreat | Spacious 1br/1bth Home
Apartment in Virginia Beach
5.0 out of 5 average rating, 17 reviewsSandbridge Beach Bay Getaway
Apartment in Corolla
4.96 out of 5 average rating, 82 reviewsThe Coastal Studio
Apartment in Virginia Beach
5.0 out of 5 average rating, 3 reviewsNEW Updated Oceanfront 2bd 2bth / Beachfront /Pool
Apartment in Norfolk
4.53 out of 5 average rating, 32 reviewsThe Willoughby Suite II - 2 Blocks from the Beach
Apartment 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
4.93 out of 5 average rating, 294 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 Portsmouth
4.98 out of 5 average rating, 40 reviewsPenny’s Palace 1 Bed/1 Bath Home
Home in Portsmouth
4.59 out of 5 average rating, 109 reviewsThe Mermaids Lair 🧜♀️
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!
Home in Hampton
4.96 out of 5 average rating, 50 reviewsExclusive Beachfront Home w/ 180° Views & Hot Tub!
Waterfront condo rentals
Condo in Williamsburg
4.94 out of 5 average rating, 105 reviewsLuxury Riverfront Condo w/ sunrise & sunset views
Condo in Virginia Beach
4.88 out of 5 average rating, 180 reviewsOceanfront Gem VaB Studio Exceptional Views
Condo in Virginia Beach
4.93 out of 5 average rating, 161 reviewsTriton’s Treasure -3 Bedroom Condo on the Beach
Condo in Virginia Beach
4.99 out of 5 average rating, 202 reviewsChic's Beach Rental and Fishing
Condo in Virginia Beach
4.85 out of 5 average rating, 131 reviewsOceanfront Penthouse
Condo in Virginia Beach
4.83 out of 5 average rating, 102 reviewsOceanfront, beachfront, boardwalk, fun, dolphins
Condo in Virginia Beach
4.92 out of 5 average rating, 114 reviewsOcean & Bay Views - Local Family Owned & Operated
Condo 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
$30 before taxes and fees
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
- Waterfront rentals United States
- Waterfront rentals Outer Banks
- Waterfront rentals Virginia Beach
- Waterfront rentals Virginia
- Rentals with a hot tub Chesapeake
- Rentals with beach access Chesapeake
- Condo rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a fire pit Chesapeake
- Private suite rentals Chesapeake
- Rentals with lake access Chesapeake
- Kid-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a home theater Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with pools Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with a washer and dryer Chesapeake
- Apartment rentals Chesapeake
- Monthly Rentals Chesapeake
- House rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Smoking-friendly rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes