Chesapeake Bay vacation rentals
Book unique homes, vacation rentals, and more on Airbnb
Top-rated vacation rentals in Chesapeake Bay
Guests agree: these vacation 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 Bay vacation rentals
Chesapeake Bay waterfront vacation rentals
Farm stay in Cardinal
4.91 out of 5 average rating, 117 reviewsWtrfrnt aptmnt w/pool/dock on private farm
Cottage in Heathsville
4.94 out of 5 average rating, 181 reviewsHedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
Cottage in Westover
4.99 out of 5 average rating, 183 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Apartment in Lexington Park
4.97 out of 5 average rating, 513 reviewsHistoric St. Mary's City, MD
Cottage in Smith Island
4.97 out of 5 average rating, 189 reviewsLevering Creek Cottage with Private Docking
Guesthouse in Yorktown
4.97 out of 5 average rating, 208 reviewsCharming Yorktown Battlefield Cottage
Home in Cape Charles
4.99 out of 5 average rating, 104 reviewsModern Private Beach House close to Cape Charles
Cottage in Leonardtown
4.97 out of 5 average rating, 128 reviewsBeach Front and 'Perfectly Placed'
Chesapeake Bay fishing vacation rentals
Apartment in Stevensville
4.98 out of 5 average rating, 242 reviewsBoutique by the Bay
Guest suite in Piney Point
4.94 out of 5 average rating, 227 reviewsSpectacular beachfront walk-out in Piney Point MD
Tiny home in Cambridge
4.89 out of 5 average rating, 504 reviewsBlackwater Tiny Cabin on Snakehead Creek
Cabin in Lusby
4.91 out of 5 average rating, 213 reviewsPeaceful Waterfront Retreat on The Bay
Guest suite in Arnold
4.96 out of 5 average rating, 571 reviewsOld Bay Bungalow
Guest suite in Colonial Beach
4.97 out of 5 average rating, 269 reviewsBayview Bungalow
Guesthouse in Church Road
5.0 out of 5 average rating, 137 reviewsHeron Rock: Lakefront Cottage on Lake Chesdin
Guest suite in Lusby
4.99 out of 5 average rating, 307 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Chesapeake Bay home rentals
Home in Heathsville
4.94 out of 5 average rating, 124 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Home in Reedville
4.96 out of 5 average rating, 205 reviewsWaterfront FamilyFriendly Home Improved for 2023
Home in Cambridge
4.92 out of 5 average rating, 183 reviewsGuest House: Farm homestead
Home in TYLERTON
4.95 out of 5 average rating, 118 reviews3 bedroom/2.5 bath Smith Island bungalow with dock
Home in Charles City
4.99 out of 5 average rating, 233 reviewsHutch's Bluff - Waterfront near Williamsburg
Home in Gloucester Courthouse
4.97 out of 5 average rating, 287 reviews"Bee-Z Haven" Waterfront Cottage on the Ware River
Home in Annapolis
4.96 out of 5 average rating, 114 reviewsHistoric Downtown in-law suite
Home in Virginia Beach
4.9 out of 5 average rating, 212 reviewsQuilted Quarters by the Bay with Private Entrance
Destinations to explore
- 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