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
Other great vacation rentals in Chesapeake Bay
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Dec 29 – Jan 5
Farm stay in Cardinal
4.95 out of 5 average rating, 107 reviewsWtrfrnt aptmnt w/pool/dock on private farm
Oct 16 – 23
Home in Virginia Beach
4.9 out of 5 average rating, 206 reviewsQuilted Quarters by the Bay with Private Entrance
Dec 4 – 11
Cabin in Deltaville
4.97 out of 5 average rating, 253 reviews"The Little Red Cabin" aka The Galley
Nov 5 – 12
Cottage in Westover
4.99 out of 5 average rating, 180 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Nov 19 – 26
Guesthouse in White Stone
5.0 out of 5 average rating, 187 reviewsWaterfront Guesthouse II on the Rappahannock
Feb 1 – 8
Cottage in Saint Leonard
4.99 out of 5 average rating, 101 reviewsCaptain Jack's Bay Hideaway
Oct 2 – 9
Guest suite in Dunnsville
5.0 out of 5 average rating, 239 reviewsThe Bird's Nest at Holly Bluff-Riverfront. Beach.
Dec 16 – 23
Chesapeake Bay home rentals
Home in Chestertown
4.94 out of 5 average rating, 128 reviewsCHESAPEAKE SUNSETS
May 4 – 11
Home in Reedville
4.96 out of 5 average rating, 203 reviewsWaterfront FamilyFriendly Home Improved for 2023
Aug 12 – 19
Home in Lusby
5.0 out of 5 average rating, 111 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Jun 25 – Jul 2
Home in Chincoteague Island
4.97 out of 5 average rating, 179 reviews★ Jay’s Waterfront Retreat: Private Dock- Kayaks-Fire Pit-Bikes-Beach-Pet Friendly ★
Jan 29 – Feb 5
Home in Gloucester
4.95 out of 5 average rating, 133 reviewsBee Humble Cottage Entire Home
Mar 12 – 19
Home in Chestertown
5.0 out of 5 average rating, 155 reviewsPet friendly, historic house, near town center.
Aug 25 – 30
Home in Blue Ridge Summit
5.0 out of 5 average rating, 450 reviewsColonial Era Spring House
Oct 3 – 10
Home in Milton
4.99 out of 5 average rating, 188 reviewsON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
Feb 12 – 19
Chesapeake Bay condo rentals
Condo in Ocean City
4.92 out of 5 average rating, 135 reviewsThe Sea Voyage Canal Front 1 Bedroom Condo
Nov 11 – 18
Condo in Ocean City
4.87 out of 5 average rating, 139 reviewsUnit 7 on 41 St Ocean Side 50 steps to beach
Oct 16 – 23
Condo in Ocean City
4.99 out of 5 average rating, 175 reviewsDirect Oceanfront close to Northside Park!
Feb 27 – Mar 6
Condo in Ocean City
4.87 out of 5 average rating, 167 reviewsBayside Retreat in the Heart of Ocean City!
Jan 15 – 22
Condo in Ocean City
4.93 out of 5 average rating, 168 reviewsCoastal and Bright Oceanfront Condo
Dec 28 – Jan 4
Condo in Ocean Pines
4.96 out of 5 average rating, 107 reviewsQuiet Water View Condo
Mar 10 – 17
Condo in Ocean City
4.97 out of 5 average rating, 223 reviewsDirect Oceanfront with a View and Amenities Galore
Nov 27 – Dec 4
Condo in Fredericksburg
4.94 out of 5 average rating, 155 reviewsCasa 1776 - Spacious Apartment | Heart of Downtown
Jan 21 – 28
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