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, 155 reviewsNicely refurbished historic house near town center
Jan 18 – 25
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Dec 25 – Jan 1
Home in Gloucester
4.95 out of 5 average rating, 133 reviewsBee Humble Cottage Entire Home
Mar 23 – 30
Home in Woolford
4.93 out of 5 average rating, 118 reviewsWaterfront Getaway with Dock
Oct 21 – 28
Home in Annapolis
4.96 out of 5 average rating, 110 reviewsHistoric Downtown in-law suite
Jan 22 – 29
Home in Shady Side
5.0 out of 5 average rating, 118 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Jan 18 – 25
Home in Milton
4.99 out of 5 average rating, 190 reviewsON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
Apr 7 – 14
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
Dec 15 – 22
Pet-friendly home rentals with a pool
Tiny home in Cape Charles
4.98 out of 5 average rating, 275 reviewsThe Laughing King Retreat Honeymoon Island Cottage
Mar 28 – Apr 4
Cottage in Berlin
4.99 out of 5 average rating, 120 reviewsBayfront Cottage w/ Amazing Views
Feb 20 – 27
Guesthouse in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
Oct 18 – 25
Guesthouse in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
Oct 11 – 18
Home in Montross
5.0 out of 5 average rating, 121 reviewsBeach Please! River cottage w/private beach & dock
Dec 4 – 11
Guest suite in Chesapeake
4.95 out of 5 average rating, 479 reviewsSweet Suite!
Nov 30 – Dec 7
Cottage in Norfolk
4.97 out of 5 average rating, 202 reviewsPositano Villa
Mar 27 – Apr 3
Guest suite in Arnold
4.97 out of 5 average rating, 129 reviewsPet Friendly Captains Quarters, Near Annapolis, EV
Jul 18 – 25
Private, pet-friendly home rentals
Guest suite in Dunnsville
5.0 out of 5 average rating, 239 reviewsThe Bird's Nest at Holly Bluff-Riverfront. Beach.
Oct 24 – 31
Cottage in Reedville
4.9 out of 5 average rating, 162 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Apr 10 – 17
Guest suite in Lusby
4.99 out of 5 average rating, 303 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Apr 24 – May 1
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Dec 20 – 27
Apartment in Church Creek
4.97 out of 5 average rating, 372 reviewsChurch Creek Natures' Rest
Nov 10 – 17
Apartment in Newport News
4.97 out of 5 average rating, 148 reviewsCentrally Located Sleek Studio Apartment
Nov 19 – 26
Apartment in Frederica
4.97 out of 5 average rating, 259 reviewsSmokefree Lakeside Relaxation
Feb 11 – 18
Tiny home in Deltaville
4.97 out of 5 average rating, 154 reviewsNan's Place aka Down Easter
Mar 16 – 23
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