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 Annapolis
4.96 out of 5 average rating, 116 reviewsHistoric Downtown in-law suite
Home in Gloucester
4.96 out of 5 average rating, 137 reviewsBee Humble Cottage Entire Home
Home in Smithfield
4.97 out of 5 average rating, 209 reviewsMason Manor - Downtown Smithfield next to WCP
Home in Tracys Landing
4.99 out of 5 average rating, 169 reviewsThe Little Gypsy BoHome
Home in Myersville
4.97 out of 5 average rating, 157 reviewsThe Crooked Cottage: a Cozy, Curated Escape
Home in Shady Side
5.0 out of 5 average rating, 122 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Home in Montross
4.91 out of 5 average rating, 149 reviewsTranquil River Home
Home in Woolford
4.93 out of 5 average rating, 122 reviewsWaterfront Getaway with Dock
Pet-friendly home rentals with a pool
Guesthouse in Highland
4.98 out of 5 average rating, 266 reviewsWoodland Retreat
Home in Irvington
5.0 out of 5 average rating, 104 reviewsEscape to magical wooded cottage with hot tub
Home in Stevensville
5.0 out of 5 average rating, 104 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Home in Montross
5.0 out of 5 average rating, 125 reviewsBeach Please! River cottage w/private beach & dock
Apartment in Lincoln
4.83 out of 5 average rating, 202 reviewsWaterfront apt. w/ pool - shopping and beaches!
Cottage in Fredericksburg
4.79 out of 5 average rating, 448 reviews1840's Cottage: 3 miles from I-95/ Near Shopping
Cottage in Berlin
4.99 out of 5 average rating, 126 reviewsBayfront Cottage w/ Amazing Views
Home in Montross
4.94 out of 5 average rating, 171 reviewsThe Glebe
Private, pet-friendly home rentals
Guest suite in Piney Point
4.94 out of 5 average rating, 229 reviewsSpectacular beachfront walk-out in Piney Point MD
Apartment in Church Creek
4.97 out of 5 average rating, 377 reviewsChurch Creek Natures' Rest
Guest suite in Colonial Beach
4.97 out of 5 average rating, 275 reviewsBayview Bungalow
Guest suite in Dunnsville
5.0 out of 5 average rating, 241 reviewsThe Bird's Nest at Holly Bluff-Riverfront. Beach.
Guest suite in Lusby
4.99 out of 5 average rating, 309 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Apartment in Frederica
4.97 out of 5 average rating, 264 reviewsSmokefree Lakeside Relaxation
Guesthouse in Saluda
4.93 out of 5 average rating, 478 reviewsWooded Cabin retreat on fresh water pond
Tiny home in Deltaville
4.97 out of 5 average rating, 155 reviewsNan's Place aka Down Easter
Destinations to explore
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- Family travel hubΒ Tips and inspiration
- Family budget travelΒ Get there for less
- Vacation ideas for any budgetΒ Make it special without making it spendy
- Travel Europe on a budgetΒ How to take the kids to Europe for less
- Outdoor adventureΒ Explore nature with the family
- Bucket list national parksΒ Must-see parks for family travel
- Kid-friendly state parksΒ Check out these family-friendly hikes