
Family-friendly rentals near Chesapeake Bay
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.
Popular amenities for family-friendly rentals near Chesapeake Bay
Family-friendly home rentals with a hot tub

Parkfront Hot Tub Haven for Families & Pets

Pet Friendly Bright In Law suite w Outdoor HangOut

Charming Annapolis Water View Home

Amazing Bay Vista Beauty with Private Pool!

Large Home with Pool & 7 bedrooms; sleeps 21

Potomac Overlook Farms: 6 BR, 10 Acre River Estate

Celebrate Summer by Your Private Pool

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa
Family- and pet-friendly home rentals

Perfect St. Michaels Getaway

Union Market Garden Apartment

Walk to famous Tiki Bar on Solomons Island!

Cozy Riverside Cottage in the Woods

Top of the Chesapeake - Private Waterfront Home

Waterman's Waypoint

Forest Hill Modern Guest House

Perfect Bay and Beach Getaway one hour from DC!
Family-friendly home rentals with a pool

Positano Villa

⛱ Quiet 3 Bed Twinhome just 3 miles from Beach! ⛱

#3 Foggy Bottom/Georgetown Apartment

Bay Breeze Retreat

Rollingside: Two-Room Guest Suite

Oceanfront Gem VaB Studio Exceptional Views

Beautiful Beach House in Rehoboth

3 BR Cottage on Mallardee Farm in Williamsburg
Family-friendly home rentals with wifi

Tiny House at Good Earth, near Bethany Beach

Cozy Private Cottage Near The Beach

Beachfront Exclusive Bay front Suite

Nautical Charm and relaxing waterview!

Gorgeous Waterfront Home!

"Queen Bee “ WATERVIEW & WALK TO ACCESS the River

Urban Cottage,MD minutes from DC/National Harbor

Edgewater Escape - Luxury Bayfront Loft with Porch
Quick stats about family-friendly rentals near Chesapeake Bay
Total rentals
4.6K properties
Total number of reviews
176K reviews
Pet-friendly rentals
2K properties allow pets
Rentals with a pool
570 properties have a pool
Rentals with dedicated workspaces
2.7K properties have a dedicated workspace
Wifi availability
4.5K properties include access to wifi
Destinations to explore
- Beach house rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- House rentals Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with an accessible-height bed Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Rentals with an accessible-height toilet Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Boutique hotel rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with a firepit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Flat rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Hotel rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Rentals with a cinema Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guest house rentals Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farm stay rentals Chesapeake Bay
- Family-friendly rentals United States
- Virginia Beach Oceanfront
- Resort Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- Kingsmill Resort
- First Landing State Park
- Buckroe Beach and Park
- Assateague Beach
- Grandview Beach
- Haven Beach
- Outlook Beach
- Ocean Breeze Waterpark
- Jamestown Settlement
- Kiptopeke Beach
- Sarah Constant Beach Park
- Norfolk Botanical Garden
- Piney Point Beach
- Wilkins Beach
- Little Creek Beach
- Cape Charles Beachfront
- Golden Horseshoe Golf Club
- Wallops Beach
- Chrysler Museum of Art
- Cabins United States
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- Yurt Rentals United States
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- Castle Rentals United States
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- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
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- Holiday Chalets United Kingdom
- Cottage Rentals United States
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- Mansion Rentals United States
- Villa Rentals United Kingdom
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- Holiday Apartments Australia
- Holiday Houses United States
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- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
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- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
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- Beach Cabins United States
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- Beach Houses United Kingdom
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- Pet-Friendly Vacation Rentals United States
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom