Pet-friendly holiday 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.
Holiday 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
18–25 Jan
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
5–12 May
Home in Gloucester
4.95 out of 5 average rating, 133 reviewsBee Humble Cottage Entire Home
24–31 Mar
Home in Woolford
4.93 out of 5 average rating, 118 reviewsWaterfront Getaway with Dock
21–28 Oct
Home in Shady Side
5.0 out of 5 average rating, 118 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
30 Nov – 7 Dec
Home in Annapolis
4.96 out of 5 average rating, 110 reviewsHistoric Downtown in-law suite
13–20 Feb
Home in Milton
4.99 out of 5 average rating, 190 reviewsON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
8–15 Apr
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
15–22 Dec
Pet-friendly home rentals with a pool
Cottage in Berlin
4.99 out of 5 average rating, 120 reviewsBayfront Cottage w/ Amazing Views
15–22 Mar
Guest house in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
6–13 Sep
Guest house in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
18–25 Jul
Guest suite in Arnold
4.97 out of 5 average rating, 129 reviewsPet Friendly Captains Quarters, Near Annapolis, EV
13–20 Oct
Home in Montross
5.0 out of 5 average rating, 121 reviewsBeach Please! River cottage w/private beach & dock
4–11 Dec
Cottage in Norfolk
4.97 out of 5 average rating, 202 reviewsPositano Villa
7–14 Jan
Guest suite in Chesapeake
4.95 out of 5 average rating, 479 reviewsSweet Suite!
19–26 Mar
Home in Ocean City
4.94 out of 5 average rating, 221 reviewsMad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
22–29 Jan
Private, pet-friendly home rentals
Cabin in Colonial Beach
4.97 out of 5 average rating, 103 reviewsSpring Perfect, Water Front A-frame on Winery
14–21 Dec
Guest suite in Dunnsville
5.0 out of 5 average rating, 239 reviewsThe Bird's Nest at Holly Bluff-Riverfront. Beach.
25 Oct – 1 Nov
Guest suite in Chestertown
4.99 out of 5 average rating, 132 reviewsChestertown - Eastern Shore Getaway
23–30 Jul
Guest suite in Richmond
4.97 out of 5 average rating, 589 reviewsForest Hill Modern Guest House
21–28 Oct
Cottage in Reedville
4.9 out of 5 average rating, 162 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
4–11 Mar
Flat in Frederica
4.97 out of 5 average rating, 259 reviewsSmokefree Lakeside Relaxation
30 Mar – 6 Apr
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
16–23 Nov
Flat in Church Creek
4.97 out of 5 average rating, 372 reviewsChurch Creek Natures' Rest
5–12 Jan
Destinations to explore
- Yurt Rentals United States
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