Pet-friendly holiday rentals in Chesapeake Bay
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Chesapeake Bay
Guests agree: these pet-friendly homes 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 Chesapeake Bay pet-friendly home rentals
Pet-friendly house rentals
Home in Reedville
4.96 out of 5 average rating, 209 reviewsWaterfront FamilyFriendly Home Improved for 2023
Home in Stevensville
5.0 out of 5 average rating, 104 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Home in Chestertown
5.0 out of 5 average rating, 157 reviewsNicely refurbished historic house near town center
Home in Tracys Landing
4.99 out of 5 average rating, 169 reviewsThe Little Gypsy BoHome
Home in Gloucester
4.96 out of 5 average rating, 137 reviewsBee Humble Cottage Entire Home
Home in Shady Side
5.0 out of 5 average rating, 122 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Home in Woolford
4.93 out of 5 average rating, 122 reviewsWaterfront Getaway with Dock
Home in Milton
4.99 out of 5 average rating, 191 reviewsON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
Pet-friendly home rentals with a pool
Cottage in Berlin
4.99 out of 5 average rating, 125 reviewsBayfront Cottage w/ Amazing Views
Guest house in Highland
4.98 out of 5 average rating, 266 reviewsWoodland Retreat
Home in Montross
5.0 out of 5 average rating, 124 reviewsBeach Please! River cottage w/private beach & dock
Cottage in Norfolk
4.97 out of 5 average rating, 205 reviewsPositano Villa
Home in Montross
4.94 out of 5 average rating, 171 reviewsThe Glebe
Home in Cambridge
4.96 out of 5 average rating, 102 reviewsWaterfront, Fabulous Home for Families with Pool!
Guest suite in Arnold
4.94 out of 5 average rating, 135 reviewsPet Friendly Captains Quarters, Near Annapolis, EV
Cabin in Greenwich
4.91 out of 5 average rating, 201 reviewsThe Hepburn-Hot Tub Pool & Fire Pit
Private, pet-friendly home rentals
Cabin in Chestertown
4.98 out of 5 average rating, 216 reviewsRivershore Retreat
Cabin in Lusby
4.91 out of 5 average rating, 215 reviewsPeaceful Waterfront Retreat on The Bay
Guest suite in Colonial Beach
4.97 out of 5 average rating, 275 reviewsBayview Bungalow
Flat in Church Creek
4.97 out of 5 average rating, 377 reviewsChurch Creek Natures' Rest
Cottage in Westover
4.92 out of 5 average rating, 146 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Guest suite in Dunnsville
5.0 out of 5 average rating, 241 reviewsThe Bird's Nest at Holly Bluff-Riverfront. Beach.
Guest house in Saluda
4.93 out of 5 average rating, 478 reviewsWooded Cabin retreat on fresh water pond
Guest suite in Lusby
4.99 out of 5 average rating, 309 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Destinations to explore
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