Pet-friendly vacation rentals in Chesapeake Bay
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Top-rated pet-friendly home rentals in Chesapeake Bay
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Chesapeake Bay pet-friendly home rentals
Pet-friendly house rentals
Home in Chestertown
5.0 out of 5 average rating, 157 reviewsNicely refurbished historic house near town center
Home in Gloucester
4.96 out of 5 average rating, 135 reviewsBee Humble Cottage Entire Home
Home in Stevensville
5.0 out of 5 average rating, 103 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Home in Tracys Landing
4.99 out of 5 average rating, 167 reviewsThe Little Gypsy BoHome
Home in Milton
4.99 out of 5 average rating, 191 reviewsON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
Home in Woolford
4.93 out of 5 average rating, 118 reviewsWaterfront Getaway with Dock
Home in Shady Side
5.0 out of 5 average rating, 120 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Home in Annapolis
4.96 out of 5 average rating, 113 reviewsHistoric Downtown in-law suite
Pet-friendly home rentals with a pool
Guesthouse in Highland
4.98 out of 5 average rating, 265 reviewsWoodland Retreat
Guesthouse in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
Cottage in Berlin
4.99 out of 5 average rating, 121 reviewsBayfront Cottage w/ Amazing Views
Home in Irvington
5.0 out of 5 average rating, 102 reviewsEscape to magical wooded cottage with hot tub
Cottage in Norfolk
4.97 out of 5 average rating, 202 reviewsVilla Positano
Guest suite in Arnold
4.97 out of 5 average rating, 132 reviewsPet Friendly Captains Quarters, Near Annapolis, EV
Guest suite in Chesapeake
4.95 out of 5 average rating, 484 reviewsSweet Suite!
Home in Montross
4.93 out of 5 average rating, 169 reviewsThe Glebe
Private, pet-friendly home rentals
Cottage in Reedville
4.9 out of 5 average rating, 164 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Cabin in Lusby
4.91 out of 5 average rating, 213 reviewsPeaceful Waterfront Retreat on The Bay
Guest suite in Colonial Beach
4.97 out of 5 average rating, 269 reviewsBayview Bungalow
Apartment in Church Creek
4.97 out of 5 average rating, 374 reviewsChurch Creek Natures' Rest
Guest suite in Dunnsville
5.0 out of 5 average rating, 239 reviewsThe Bird's Nest at Holly Bluff-Riverfront. Beach.
Guesthouse in Church Road
5.0 out of 5 average rating, 137 reviewsHeron Rock: Lakefront Cottage on Lake Chesdin
Cottage in Westover
4.92 out of 5 average rating, 144 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Cabin in Chestertown
4.98 out of 5 average rating, 215 reviewsRivershore Retreat
Destinations to explore
- Yurt Rentals United States
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