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
Apartment in Williamsburg
4.92 out of 5 average rating, 237 reviewsHistoric Powhatan Resort- 2 bedroom condo!
7–12 May
Condo in Williamsburg
4.86 out of 5 average rating, 14 reviewsMarriott Manor Club Luxury Studio sleeps 4
2–9 Jan
Home in Virginia Beach
4.61 out of 5 average rating, 109 reviewsCroatan Beach - Big Kitchen, Hot Tub, 2 Masters
9–16 Nov
Apartment in Williamsburg
4.88 out of 5 average rating, 48 reviews★Colonial Wmbg/Busch Gardens 1BR★ ppr (#4)
26 Jul – 2 Aug
Condo in Williamsburg
4.71 out of 5 average rating, 14 reviewsTimeshare Resort condo- 1 bdrm
18–25 Jun
Condo in Virginia Beach
4.82 out of 5 average rating, 11 reviews1 BR/Kitchen w/Balcony, Beach Quarters Oceanfront
15–22 Jun
Townhouse in Williamsburg
5.0 out of 5 average rating, 8 reviews4BDR in fun family resort. Best bargain in town.
29 Jun – 6 Jul
Apartment in Williamsburg
4.92 out of 5 average rating, 75 reviews*Historic Powhatan Resort- 2 bedroom
3–10 Jun
Family- and pet-friendly home rentals
Home in Virginia Beach
4.77 out of 5 average rating, 149 reviewsChic's Beach Retreat
19–26 Oct
Bungalow in Hampton
4.89 out of 5 average rating, 201 reviewsBungelow by The Beach 2BR 1BA CABLE-Hampton, VA
16–23 Feb
Cottage in Williamsburg
4.84 out of 5 average rating, 515 reviewsThe Colonial Cottage
14–21 Jan
Cottage in Corolla
4.87 out of 5 average rating, 126 reviewsHorses-Views-Dog Friendly-4WD Area
16–23 Mar
Home in Virginia Beach
4.89 out of 5 average rating, 294 reviewsLess than one mile to ocean, 3 bedrooms
11–18 Dec
Home in Virginia Beach
4.99 out of 5 average rating, 128 reviewsQuiet family location and close to BEACH!
9–16 Dec
Apartment in Williamsburg
4.82 out of 5 average rating, 146 reviewsWestgate Historic Williamsburg One Bedroom
19–26 Feb
Cottage in Corolla
4.87 out of 5 average rating, 174 reviewsQuaint Beach Cottage in 4WD-OBX
13–20 Mar
Family-friendly home rentals with a pool
Home in Virginia Beach
4.83 out of 5 average rating, 106 reviewsStunning Views of Back Bay & Seconds to the Beach
29 Oct – 5 Nov
Apartment in Virginia Beach
4.87 out of 5 average rating, 78 reviewsBeach Nut - Virginia Beach Oceanfront!
24 Sep – 1 Oct
Guesthouse in Virginia Beach
4.66 out of 5 average rating, 80 reviewsPOOL, Pool House, Hot Tub, Grill, 2 bedroom
Home in Cape Charles
4.76 out of 5 average rating, 74 reviewsFamily Retreat, In-Ground Pool, plus Private Beach
14–21 Nov
Home in Virginia Beach
4.9 out of 5 average rating, 119 reviewsBeach Home, Upscale Croatan Resort + Private Pool
26 Feb – 5 Mar
Apartment in Virginia Beach
4.88 out of 5 average rating, 24 reviewsOceanview Queen & Sofa Bed, Kitchenette, Balcony-D
14–21 Sep
Condo in Virginia Beach
4.82 out of 5 average rating, 50 reviewsSeas The Day of Virginia Beach
6–13 Dec
Home in Virginia Beach
4.73 out of 5 average rating, 80 reviews7+ Bdrm, 5.5 Bath Pool/Hot Tub Sandbridge Beach VA
15–22 Dec
Quick stats about holiday rentals that are family-friendly in Chesapeake
Total rentals
510 properties
Wi-Fi availability
500 properties include access to Wi-Fi
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
- Jersey City Holiday rentals
- New York Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Outer Banks
- Family-friendly rentals Virginia Beach
- Family-friendly rentals Virginia
- Rentals with lake access Chesapeake
- Apartment rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Condo rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Waterfront rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with a patio Chesapeake
- Private suite rentals Chesapeake
- Rentals with a home theatre Chesapeake
- Smoking-friendly rentals Chesapeake
- House rentals Chesapeake
- Monthly Rentals Chesapeake
- Pet-friendly rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with beach access Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with pools Chesapeake
- Kid-friendly rentals Chesapeake
- Rentals with breakfast Chesapeake
- 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