Pet-friendly vacation 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.
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, 156 reviewsNicely refurbished historic house near town center
Mar 14 – 21
Home in Stevensville
5.0 out of 5 average rating, 102 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Jan 22 – 29
Home in Gloucester
4.96 out of 5 average rating, 134 reviewsBee Humble Cottage Entire Home
Dec 9 – 16
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 19 – 26
Home in Montross
4.91 out of 5 average rating, 147 reviewsTranquil River Home
Apr 3 – 10
Home in Annapolis
4.96 out of 5 average rating, 112 reviewsHistoric Downtown in-law suite
Mar 23 – 30
Home in Woolford
4.93 out of 5 average rating, 118 reviewsWaterfront Getaway with Dock
Nov 3 – 10
Home in Shady Side
5.0 out of 5 average rating, 119 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Apr 28 – May 5
Pet-friendly home rentals with a pool
Home in Irvington
5.0 out of 5 average rating, 101 reviewsEscape to magical wooded cottage with hot tub
Jan 20 – 27
Guesthouse in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
Sep 6 – 13
Guesthouse in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
Oct 16 – 23
Cottage in Berlin
4.99 out of 5 average rating, 120 reviewsBayfront Cottage w/ Amazing Views
Mar 25 – Apr 1
Home in Montross
5.0 out of 5 average rating, 122 reviewsBeach Please! River cottage w/private beach & dock
Nov 7 – 14
Guest suite in Arnold
4.97 out of 5 average rating, 130 reviewsPet Friendly Captains Quarters, Near Annapolis, EV
Sep 24 – Oct 1
Cottage in Norfolk
4.97 out of 5 average rating, 202 reviewsPositano Villa
Feb 6 – 13
Home in Montross
4.93 out of 5 average rating, 167 reviewsThe Glebe
Dec 4 – 11
Private, pet-friendly home rentals
Guest suite in Piney Point
4.94 out of 5 average rating, 225 reviewsSpectacular beachfront walk-out in Piney Point MD
Dec 31 – Jan 7
Guest suite in Colonial Beach
4.97 out of 5 average rating, 266 reviewsBayview Bungalow
Sep 29 – Oct 6
Guest suite in Lusby
4.99 out of 5 average rating, 305 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Sep 23 – 30
Apartment in Church Creek
4.97 out of 5 average rating, 373 reviewsChurch Creek Natures' Rest
Jul 7 – 14
Apartment in Newport News
4.97 out of 5 average rating, 148 reviewsCentrally Located Sleek Studio Apartment
Jan 10 – 17
Tiny home in Deltaville
4.97 out of 5 average rating, 154 reviewsNan's Place aka Down Easter
Dec 20 – 27
Cabin in Colonial Beach
4.97 out of 5 average rating, 105 reviewsSpring Perfect, Water Front A-frame on Winery
Nov 13 – 20
Guesthouse in Saluda
4.93 out of 5 average rating, 471 reviewsWooded Cabin retreat on fresh water pond
Nov 16 – 23
Destinations to explore
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