Kid-friendly holiday rentals in Chesapeake
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Chesapeake
Guests agree: these family-friendly rentals 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
Kid-friendly house rentals
Home in Virginia Beach
4.9 out of 5 average rating, 209 reviewsQuilted Quarters by the Bay with Private Entrance
23–30 Jan
Home in Smithfield
4.97 out of 5 average rating, 205 reviewsMason Manor - Downtown Smithfield next to WCP
13–20 Mar
Home in Moyock
4.93 out of 5 average rating, 286 reviewsSportsman's Paradise ( Hunting & Fishing )
25 Oct – 1 Nov
Home in East Ocean View
4.84 out of 5 average rating, 122 reviewsCozy Coastal Home
11–18 Nov
Home in Hampton
4.95 out of 5 average rating, 123 reviews1950s bungalow, 2-1/2 blocks from Buckroe Beach
9–16 Dec
Home in Hampton
4.97 out of 5 average rating, 177 reviewsThe Water's Edge
9–16 Oct
Home in Virginia Beach
4.87 out of 5 average rating, 212 reviewsChicks Beachfront
20–27 Mar
Home in Norfolk
4.98 out of 5 average rating, 103 reviewsBeach House on the Bay
30 Aug – 6 Sept
Family-friendly apartment rentals
Flat in Portsmouth
4.86 out of 5 average rating, 413 reviewsStylish 2 bedroom apt in historic Port Norfolk
20–27 Oct
Flat in Virginia Beach
4.9 out of 5 average rating, 187 reviewsVB Oceanfront Studio Balcony,Beach,Boardwalk, Pool
26 Jan – 2 Feb
Flat in Portsmouth
4.96 out of 5 average rating, 242 reviewsCozy Ground Floor Apt in Historic Home
7–14 Nov
Flat in Chesapeake
5.0 out of 5 average rating, 145 reviewsModern Luxury Peace & Quiet.
13–20 Jan
Flat in Hampton
4.97 out of 5 average rating, 127 reviewsDowntown Hampton's Hidden Gem with Queen Bed
18–25 May
Flat in Portsmouth
4.96 out of 5 average rating, 106 reviewsBest location in Olde Towne Portsmouth
18–25 Oct
Flat in Virginia Beach
4.91 out of 5 average rating, 467 reviewsPrivate apartment only 3 blocks from the Beach
27 Aug – 3 Sept
Flat in Virginia Beach
4.94 out of 5 average rating, 206 reviewsTree Top Beach Bungalow 3 1/2 blocks fr beach
4–11 Jan
Family-friendly apartment rentals
Apartment in Norfolk
4.79 out of 5 average rating, 155 reviewsBest Value Condo in Downtown Norfolk
28 Jul – 4 Aug
Apartment in Downtown Norfolk
4.86 out of 5 average rating, 160 reviewsModern And Cozy!
8–15 May
Apartment in Virginia Beach
4.86 out of 5 average rating, 207 reviewsOcean Escape
4–11 Oct
Apartment in Virginia Beach
4.93 out of 5 average rating, 247 reviews2 bedroom condo with oceanfront one block away!
12–19 Aug
Apartment in Virginia Beach
4.93 out of 5 average rating, 160 reviewsTriton’s Treasure -3 Bedroom Condo on the Beach
19–26 Apr
Apartment in Virginia Beach
4.85 out of 5 average rating, 110 reviewsNEW! Beach Paradise Studio on the Boardwalk w/Pool
24 Sept – 1 Oct
Apartment in Williamsburg
4.94 out of 5 average rating, 105 reviewsLuxury Riverfront Condo w/ sunrise & sunset views
18–25 Nov
Apartment in Williamsburg
4.95 out of 5 average rating, 130 reviewsKingsmill 1bed/1ba on Golf Course 9th Fairway
24–31 Oct
Quick stats about holiday rentals that are kid-friendly in Chesapeake
Total rentals
190 properties
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
90 properties allow pets
Family-friendly rentals
130 properties are a good fit for families
Total number of reviews
8K reviews
Nightly prices starting at
£24 before taxes and fees
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
- Family-friendly rentals Outer Banks
- Family-friendly rentals Virginia Beach
- Family-friendly rentals Virginia
- Family-friendly rentals Richmond
- Rentals with an EV charger Chesapeake
- Waterfront rentals Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a firepit Chesapeake
- Monthly Rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with lake access Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with pools Chesapeake
- Apartment rentals Chesapeake
- Flat rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with beach access Chesapeake
- Rentals with a fireplace Chesapeake
- Smoking-friendly rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Townhouse rentals Chesapeake
- Rentals with a cinema Chesapeake
- Rentals with a patio Chesapeake
- House rentals 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