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 13 – 20
Home in Montross
4.92 out of 5 average rating, 146 reviewsTranquil River Home
Apr 2 – 9
Home in Woolford
4.93 out of 5 average rating, 118 reviewsWaterfront Getaway with Dock
Oct 21 – 28
Home in Shady Side
5.0 out of 5 average rating, 118 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Nov 11 – 18
Home in Annapolis
4.96 out of 5 average rating, 111 reviewsHistoric Downtown in-law suite
Jan 25 – Feb 1
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
May 30 – Jun 6
Home in Smithfield
4.97 out of 5 average rating, 205 reviewsMason Manor - Downtown Smithfield next to WCP
Dec 23 – 30
Pet-friendly home rentals with a pool
Guesthouse in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
Oct 18 – 25
Cottage in Berlin
4.99 out of 5 average rating, 120 reviewsBayfront Cottage w/ Amazing Views
Feb 6 – 13
Guesthouse in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
Sep 22 – 29
Home in Irvington
5.0 out of 5 average rating, 101 reviewsEscape to magical wooded cottage with hot tub
Aug 7 – 14
Home in Montross
5.0 out of 5 average rating, 122 reviewsBeach Please! River cottage w/private beach & dock
Nov 7 – 14
Cottage in Norfolk
4.97 out of 5 average rating, 202 reviewsPositano Villa
Mar 30 – Apr 6
Guest suite in Arnold
4.97 out of 5 average rating, 129 reviewsPet Friendly Captains Quarters, Near Annapolis, EV
Sep 22 – 29
Guest suite in Chesapeake
4.95 out of 5 average rating, 479 reviewsSweet Suite!
Mar 17 – 24
Private, pet-friendly home rentals
Guest suite in Colonial Beach
4.97 out of 5 average rating, 263 reviewsBayview Bungalow
Sep 28 – Oct 5
Guest suite in Dunnsville
5.0 out of 5 average rating, 239 reviewsThe Bird's Nest at Holly Bluff-Riverfront. Beach.
Aug 27 – Sep 3
Guest suite in Richmond
4.97 out of 5 average rating, 590 reviewsForest Hill Modern Guest House
Oct 20 – 27
Cottage in Reedville
4.9 out of 5 average rating, 162 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Dec 14 – 21
Apartment in Church Creek
4.97 out of 5 average rating, 372 reviewsChurch Creek Natures' Rest
Feb 16 – 23
Apartment in Frederica
4.97 out of 5 average rating, 259 reviewsSmokefree Lakeside Relaxation
Apr 19 – 26
Cabin in Colonial Beach
4.97 out of 5 average rating, 105 reviewsSpring Perfect, Water Front A-frame on Winery
Nov 13 – 20
Guest suite in Lusby
4.99 out of 5 average rating, 303 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Nov 30 – Dec 7
Destinations to explore
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