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.

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Superhost

Guest suite in Virginia Beach

4.89 out of 5 average rating, 551 reviews

Quiet Neighborhood 7 Miles From the Beaches

Be sure to read about the pricing using both bedrooms below in 2nd paragraph. My house is in a quiet neighborhood by a creek of the Lynnhaven River 7 miles from the Oceanfront/Chesapeake Bay with easy access to the interstate and surrounding cities in Hampton Roads. Only minutes from Town Center and local malls. Your private area is the 1st level with your own private entrance, but no kitchen. There is small microwave and a coffee machine in the unit , & a small fridge on the screened-in-porch.

1 – 8 Nov

$1,126 AUD total

Superhost

Apartment in Virginia Beach

4.91 out of 5 average rating, 466 reviews

Private apartment only 3 blocks from the Beach

Newly remodeled, super clean one bedroom (in-law) apartment, approx. 375 sf. Three blocks from the beach 7-10 min walk. Covered deck, backyard on water to watch ducks, herons, fish. Concrete benches and firepit near the water. Walking distance to the ocean, boardwalk, Rudee Inlet, dining and entertainment. Hardwood floors, queen size bed, 'pack n play', kitchenette with sink, refrigerator, microwave, Keurig coffee maker, toaster (no oven or stove) 500 mbps Wifi, internet tv. Futon-like couch.

7 – 14 June

$2,176 AUD total

Guest favourite

Condo in Virginia Beach

4.94 out of 5 average rating, 221 reviews

2 Bedroom Beach Condo Block Off Boardwalk

Come enjoy everything Virginia Beach has to offer. Our newly renovated condo has all of the comforts of home and accommodates 6 adults or perfect for families. Bedroom 1 has a king size bed, bedroom 2 has a queen size bed, and Living room has sofa that pulls out into a full size sofa bed. TVs in all rooms. The Boardwalk, Shopping, Restaurants, and many more activities are all within walking distance. There is plenty to do for the whole family. Come have a relaxing and fun vacation at the beach.

4 – 11 Aug

$4,674 AUD total

Guest favourite

Condo in Virginia Beach

4.88 out of 5 average rating, 150 reviews

Oceanfront Jewel VB Studio Mesmerizing Ocean View

Newly remodeled, stunning panoramic oceanfront views from the 3rd floor at the peaceful north end of Va Beach boardwalk. Perfect for two, this cozy 355 sq ft studio with wireless internet, large screen TV and full kitchen, has a community pool, back patio, charming beach lawn with tables & lounge chairs and is walking distance to outstanding restaurants, attractions and shopping. Beach chairs and towels provided. Please note: due to the open layout of the building, there is no elevator.

15 – 22 Sept

$3,669 AUD total

Guest favourite

Apartment in Hampton

4.96 out of 5 average rating, 364 reviews

"Shangri-La", of Hampton, Virginia

2nd story 1200 square foot apartment with 2 BR's, Wi-Fi, microwave, fridge and bar with sink. Walk in glass enclosed shower & soaker tub. Private deck with gas grill down the spiral stairs below on ground level patio. Pool table in BnB. We share our pool with our BnB guests seasonally. Please inquire about pool availability if important to your booking. Local history, sites, nature and beaches abound. Security cameras surround the exterior of our home for our protection as well as yours!

16 – 23 Dec

$1,861 AUD total

Guest favourite

Guest suite in Virginia Beach

4.98 out of 5 average rating, 278 reviews

Home away from home~Private,quiet, mins to bay

Home away from home is a spacious, comfortable, and private apartment with 1 Queen bedroom, full bath w/ tub, living area, work space, and fully equipped kitchen. Conveniently and centrally located in historic neighborhood: 3 mins to bay, 15 mins to oceanfront. We are within 4 miles of Norfolk Premium Outlets and IKEA, and are within 5 miles to Virginia Wesleyan and 15 miles to ODU. Walk to local favorite restaurants (New River Tap House, The Rustic Spoon, 1608 Crafthouse, Comfy Belly).

30 June – 7 July

$2,421 AUD total

Guest favourite

Guest suite in Carrollton

4.98 out of 5 average rating, 161 reviews

2BR 1BA Spacious Guest Suite, Woods & Water Views

NO CLEANING FEES CHARGED! ONLY YOU/YOUR TRAVEL COMPANION ARE GUESTS in the private, in home, upstairs 2 BR 1 BATH GUEST SUITE W/MINI-KITCHEN. 1 guest per bedroom, only (see accommodations policy below). Nothing fancy, but clean, pretty. & relaxingly comfy. Serene, wooded, retreat like setting on a small lake w/wildlife. Centrally located. Visit Williamsburg one day & VA Beach the next. Near Smithfield, universities & military bases. Discount for active military & nurses.

5 – 12 Feb

$1,248 AUD total

Superhost

Guest suite in Virginia Beach

4.95 out of 5 average rating, 345 reviews

Cozy Beachy Vacation Suite with Private Entrance

Enjoy your stay in a newly renovated ground floor suite with your own private entrance. You can watch TV, catch up on some writing, or have a snack in the den. Feel free to make a small meal in the kitchenette, or order dinner to be delivered. You can brew coffee anytime you like. After enjoying a long day exploring, take a nice hot bath or shower in your own bathroom. You will have a "good nights sleep" in the queen sized bed to get ready for a new day in Virginia Beach.

$145 AUD per night

Guest favourite

Cottage in Norfolk

4.97 out of 5 average rating, 202 reviews

Positano Villa

This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

12 – 19 Mar

$5,301 AUD total

Guest favourite

Home in Virginia Beach

4.78 out of 5 average rating, 130 reviews

Quaint 2 Bedroom Cottage in Chicks Beach

2 bedroom 1 bathroom quaint cottage, walking distance only 2 blocks to the beach . The beach is great for families with children . This unit is connected to a 1 bedroom unit . Back yard has a single detached unit also . Great for small families. There is a fenced in front yard Back yard and laundry area is shared with guest suite next door. 2 Car max allowed $75 pet fee with pre approval. Starting June 25th 7 night min check in on Friday only !

23 – 30 Aug

$2,612 AUD total

Guest favourite

Home in Williamsburg

4.97 out of 5 average rating, 178 reviews

Casita on the Corner

Our cozy little 2 bedroom, one bath, small dog friendly home is on a corner lot in a family friendly neighborhood just minutes from major attractions like Busch Gardens/Water Country. This area is rich with historical sites. Be sure to visit Colonial Williamsburg, Jamestown and Yorktown. Take a tour on The Colonial Parkway or If you are a cyclist bring your bike and ride the Capitol trail or hit the trails at Freedom Park or New Quarter Park.

6 – 13 Dec

$1,674 AUD total

Superhost

Guest suite in Norfolk

4.93 out of 5 average rating, 507 reviews

Beachfront Exclusive Bay front Suite

This comfortable private beachfront suite with kitchenette has magnificent views of the sunrise and sunset that you can enjoy from your own private deck, with a 180 degree views of the beach front with easy access to the water's edge, just steps away. If you want to experience life on the beach this is as close as you can get. This suite represents our personalities and everything we love about living at the beach on the Chesapeake Bay

14 – 21 Sept

$2,801 AUD total