Family-friendly holiday rentals in Chesapeake Beach
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chesapeake Beach
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 Beach family-friendly rentals
Family-friendly home rentals with a hot tub
Flat in Williamsburg
4.92 out of 5 average rating, 237 reviewsHistoric Powhatan Resort- 2 bedroom condo!
7–12 May
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 Virginia Beach
4.82 out of 5 average rating, 11 reviews1 BR/Kitchen w/Balcony, Beach Quarters Oceanfront
15–22 Jun
Apartment in Williamsburg
4.86 out of 5 average rating, 14 reviewsMarriott Manor Club Luxury Studio sleeps 4
2–9 Jan
Flat in Williamsburg
4.88 out of 5 average rating, 48 reviews★Colonial Wmbg/Busch Gardens 1BR★ ppr (#4)
26 Jul – 2 Aug
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
4.71 out of 5 average rating, 14 reviewsTimeshare Resort condo- 1 bdrm
18–25 Jun
Flat 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
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
Cottage in Corolla
4.87 out of 5 average rating, 126 reviewsHorses-Views-Dog Friendly-4WD Area
16–23 Mar
Cottage in Williamsburg
4.84 out of 5 average rating, 515 reviewsThe Colonial Cottage
14–21 Jan
Flat in Williamsburg
4.82 out of 5 average rating, 146 reviewsWestgate Historic Williamsburg One Bedroom
19–26 Feb
Home in Lanexa
4.95 out of 5 average rating, 172 reviewsWilliamsburg Hide-A-Way Creekside
17–24 Jul
Family-friendly home rentals with a pool
Farm stay in Williamsburg
4.96 out of 5 average rating, 319 reviews3 BR Cottage on Mallardee Farm in Williamsburg
12–19 Feb
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
Flat in Virginia Beach
4.87 out of 5 average rating, 78 reviewsBeach Nut - Virginia Beach Oceanfront!
24 Sep – 1 Oct
Home in Virginia Beach
4.99 out of 5 average rating, 68 reviewsBreathtaking Ocean views at Pinch Me, 8bdrm, 6bath
1–8 Feb
Home in Cape Charles
4.76 out of 5 average rating, 74 reviewsFamily Retreat, In-Ground Pool, plus Private Beach
14–21 Nov
Guest house in Virginia Beach
4.66 out of 5 average rating, 80 reviewsPOOL, Pool House, Hot Tub, Grill, 2 bedroom
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
4.82 out of 5 average rating, 50 reviewsSeas The Day of Virginia Beach
6–13 Dec
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 Beach
- Family-friendly rentals Virginia
- Rentals with pools Chesapeake Beach
- Monthly Rentals Chesapeake Beach
- Rentals with a patio Chesapeake Beach
- Rentals with a fireplace Chesapeake Beach
- Pet-friendly rentals Chesapeake Beach
- Family-friendly rentals Chesapeake Beach
- Rentals with outdoor seating Chesapeake Beach
- House rentals Chesapeake Beach
- Rentals with beach access Chesapeake Beach
- Hotel rentals Chesapeake Beach
- Fitness-friendly rentals Chesapeake Beach
- Beachfront rentals Chesapeake Beach
- Rentals with a washing machine and dryer Chesapeake Beach
- 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