Family-friendly holiday rentals in Chesapeake
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chesapeake
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake family-friendly rentals
Family-friendly home rentals with a hot tub
Serviced apartment in Williamsburg
4.88 out of 5 average rating, 125 reviewsHistoric Powhatan Resort- 2 bedroom condo!
Apartment in Williamsburg
4.73 out of 5 average rating, 15 reviewsTimeshare Resort condo- 1 bdrm
Apartment in Williamsburg
4.94 out of 5 average rating, 35 reviewsMarriott's Manor Club Ford's Colony 2BD Villa Slee
Home in Virginia Beach
4.61 out of 5 average rating, 109 reviewsCroatan Beach - Big Kitchen, Hot Tub, 2 Masters
Apartment in Virginia Beach
4.82 out of 5 average rating, 11 reviews1 BR/Kitchen w/Balcony, Beach Quarters Oceanfront
Townhouse in Williamsburg
5.0 out of 5 average rating, 8 reviews4BDR in fun family resort. Best bargain in town.
Serviced apartment in Williamsburg
4.92 out of 5 average rating, 75 reviews*Historic Powhatan Resort- 2 bedroom
Home in Norfolk
4.75 out of 5 average rating, 4 reviewsLIFE ON A SANDBAR! STAY ON THE BEACH!
Family- and pet-friendly home rentals
Home in Virginia Beach
4.95 out of 5 average rating, 107 reviewsWater Oaks at Chic's Beach
Home in Virginia Beach
4.79 out of 5 average rating, 132 reviewsQuaint 2 Bedroom Cottage in Chicks Beach
Home in Virginia Beach
4.89 out of 5 average rating, 294 reviewsLess than one mile to ocean, 3 bedrooms
Bungalow in Hampton
4.89 out of 5 average rating, 203 reviewsBungelow by The Beach 2BR 1BA CABLE-Hampton, VA
Home in Virginia Beach
4.99 out of 5 average rating, 129 reviewsQuiet family location and close to BEACH!
Cottage in Corolla
4.87 out of 5 average rating, 127 reviewsHorses-Views-Dog Friendly-4WD Area
Flat in Williamsburg
4.82 out of 5 average rating, 147 reviewsWestgate Historic Williamsburg One Bedroom
Cottage in Williamsburg
4.84 out of 5 average rating, 519 reviewsThe Colonial Cottage
Family-friendly home rentals with a pool
Farm stay in Williamsburg
4.96 out of 5 average rating, 320 reviews3 BR Cottage on Mallardee Farm in Williamsburg
Home in Virginia Beach
4.83 out of 5 average rating, 106 reviewsStunning Views of Back Bay & Seconds to the Beach
Tiny home in Virginia Beach
4.85 out of 5 average rating, 13 reviewsAmazing Sunsets! Sandbridge Waterfront/Back Bay
Flat in Virginia Beach
4.87 out of 5 average rating, 78 reviewsBeach Nut - Virginia Beach Oceanfront!
Guest house in Virginia Beach
4.67 out of 5 average rating, 82 reviewsPOOL, Pool House, Hot Tub, Grill, 2 bedroom
Home in Virginia Beach
4.99 out of 5 average rating, 70 reviewsBreathtaking Ocean views at Pinch Me, 8bdrm, 6bath
Home in Cape Charles
4.76 out of 5 average rating, 74 reviewsFamily Retreat, In-Ground Pool, plus Private Beach
Home in Corolla
4.87 out of 5 average rating, 53 reviewsBeautiful Corolla Beachhouse Steps From the Water
Quick stats about holiday rentals that are family-friendly in Chesapeake
Total rentals
510 properties
Wifi availability
500 properties include access to wifi
Rentals with dedicated workspaces
320 properties have a dedicated workspace
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
200 properties allow pets
Total number of reviews
14K reviews
Destinations to explore
- Outer Banks Holiday rentals
- Virginia Beach Holiday rentals
- Richmond Holiday rentals
- Norfolk Holiday rentals
- Williamsburg Holiday rentals
- Nags Head Holiday rentals
- Myrtle Beach Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- Family-friendly rentals United States
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- Family-friendly rentals Virginia
- Rentals with a cinema Chesapeake
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