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
Get the amount of space that is right for you.
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
Jan. 19 – 26
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
Apartment in Church Creek
4.97 out of 5 average rating, 372 reviewsChurch Creek Natures' Rest
Feb. 16 – 23
Cottage in Reedville
4.9 out of 5 average rating, 162 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Dec. 14 – 21
Cabin in Colonial Beach
4.97 out of 5 average rating, 105 reviewsSpring Perfect, Water Front A-frame on Winery
Nov. 13 – 20
Apartment in Frederica
4.97 out of 5 average rating, 259 reviewsSmokefree Lakeside Relaxation
Apr. 19 – 26
Guest suite in Lusby
4.99 out of 5 average rating, 303 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Nov. 30 – Dec. 7
Tiny homes in Deltaville
4.97 out of 5 average rating, 154 reviewsNan's Place aka Down Easter
Sep. 4 – 11
Destinations to explore
- Yurt Rentals United States
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