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, 156 reviewsNicely refurbished historic house near town center
Dec 11 – 18
Home in Stevensville
5.0 out of 5 average rating, 102 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Nov 25 – Dec 2
Home in Chincoteague
4.98 out of 5 average rating, 196 reviews★ Pearl in the Pines: Kayaks-Fire Pit-Bikes-Beach-Pet Friendly
Feb 5 – 12
Home in Annapolis
4.96 out of 5 average rating, 112 reviewsHistoric Downtown in-law suite
Mar 28 – Apr 4
Home in Woolford
4.93 out of 5 average rating, 118 reviewsWaterfront Getaway with Dock
Nov 3 – 10
Home in Montross
4.91 out of 5 average rating, 147 reviewsTranquil River Home
Mar 18 – 25
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
Mar 27 – Apr 3
Home in Milton
4.99 out of 5 average rating, 191 reviewsON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
Mar 11 – 18
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
Sep 10 – 17
Cottage in Berlin
4.99 out of 5 average rating, 121 reviewsBayfront Cottage w/ Amazing Views
Dec 13 – 20
Guesthouse in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
Aug 18 – 25
Guest suite in Chesapeake
4.95 out of 5 average rating, 482 reviewsSweet Suite!
Jan 17 – 24
Home in Montross
5.0 out of 5 average rating, 122 reviewsBeach Please! River cottage w/private beach & dock
Jan 23 – 30
Cottage in Norfolk
4.97 out of 5 average rating, 202 reviewsPositano Villa
Mar 9 – 16
Guest suite in Arnold
4.97 out of 5 average rating, 131 reviewsPet Friendly Captains Quarters, Near Annapolis, EV
Aug 25 – Sep 1
Home in Montross
4.93 out of 5 average rating, 167 reviewsThe Glebe
Dec 4 – 11
Private, pet-friendly home rentals
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 Chestertown
4.99 out of 5 average rating, 132 reviewsChestertown - Eastern Shore Getaway
Aug 17 – 24
Apartment in Church Creek
4.97 out of 5 average rating, 373 reviewsChurch Creek Natures' Rest
Mar 13 – 20
Apartment in Frederica
4.97 out of 5 average rating, 260 reviewsSmokefree Lakeside Relaxation
Oct 14 – 21
Cabin in Lusby
4.91 out of 5 average rating, 211 reviewsPeaceful Waterfront Retreat on The Bay
Dec 12 – 19
Tiny home in Accomac
4.93 out of 5 average rating, 442 reviewsLittle Red House on a Farm - Quiet Rural Waterview
Apr 16 – 23
Guest suite in Colonial Beach
4.97 out of 5 average rating, 266 reviewsBayview Bungalow
Aug 25 – Sep 1
Apartment in Newport News
4.97 out of 5 average rating, 148 reviewsCentrally Located Sleek Studio Apartment
Dec 11 – 18
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