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
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 Gloucester
4.95 out of 5 average rating, 133 reviewsBee Humble Cottage Entire Home
Feb 17 – 24
Home in Chestertown
5.0 out of 5 average rating, 155 reviewsPet friendly, 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!
Mar 8 – 15
Home in Milton
4.99 out of 5 average rating, 189 reviewsON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
Apr 11 – 18
Home in Annapolis
4.96 out of 5 average rating, 109 reviewsHistoric Downtown in-law suite
Apr 4 – 11
Home in Shady Side
5.0 out of 5 average rating, 116 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Jan 2 – 9
Home in Woolford
4.93 out of 5 average rating, 118 reviewsWaterfront Getaway with Dock
Nov 3 – 10
Home in Smithfield
4.97 out of 5 average rating, 204 reviewsMason Manor - Downtown Smithfield next to WCP
Dec 18 – 25
Pet-friendly home rentals with a pool
Tiny home in Cape Charles
4.98 out of 5 average rating, 273 reviewsThe Laughing King Retreat Honeymoon Island Cottage
Jan 5 – 12
Guesthouse in Highland
4.98 out of 5 average rating, 263 reviewsWoodland Retreat
Sep 18 – 25
Cottage in Berlin
4.99 out of 5 average rating, 119 reviewsBayfront Cottage w/ Amazing Views
Feb 6 – 13
Home in Montross
5.0 out of 5 average rating, 120 reviewsBeach Please! River cottage w/private beach & dock
Oct 1 – 8
Home in Irvington
5.0 out of 5 average rating, 101 reviewsEscape to magical wooded cottage with hot tub
Aug 25 – Sep 1
Guest suite in Chesapeake
4.95 out of 5 average rating, 479 reviewsSweet Suite!
Jan 3 – 10
Guesthouse in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
Jul 30 – Aug 6
Cottage in Norfolk
4.97 out of 5 average rating, 201 reviewsPositano Villa
Feb 23 – Mar 2
Private, pet-friendly home rentals
Tiny home in Accomac
4.93 out of 5 average rating, 440 reviewsLittle Red House on a Farm - Quiet Rural Waterview
Apr 11 – 18
Cottage in Kinsale
4.95 out of 5 average rating, 195 reviewsGreat little cottage with a "Rivah" view
Apr 13 – 20
Apartment in Frederica
4.97 out of 5 average rating, 258 reviewsSmokefree Lakeside Relaxation
Oct 27 – Nov 3
Guest suite in Piney Point
4.94 out of 5 average rating, 225 reviewsSpectacular beachfront walk-out in Piney Point MD
Oct 7 – 14
Guest suite in Dunnsville
5.0 out of 5 average rating, 239 reviewsThe Bird's Nest at Holly Bluff-Riverfront. Beach.
Aug 19 – 26
Tiny home in Deltaville
4.97 out of 5 average rating, 154 reviewsNan's Place aka Down Easter
Jan 8 – 15
Guest suite in Lusby
4.99 out of 5 average rating, 303 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Dec 5 – 12
Cabin in Colonial Beach
4.97 out of 5 average rating, 102 reviewsSpring Perfect, Water Front A-frame on Winery
Nov 9 – 16
Destinations to explore
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom