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.

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Guest favourite

Guest suite in Virginia Beach

4.97 out of 5 average rating, 234 reviews

Scott's Garden Suite At The Crooked House

Just blocks from the beach, Scott's Garden Suite is nestled in the back yard of one of southside's desireable neighborhoods. With a spacious, queen bedroom & small reading/sleeping den, this little private hideaway is ideal for 2/3 adults or small family. Adjacent to the ViBe Art District/restaurants/shopping, it has kitchenette, 3/4 bath & outdoor LR with gas fire table. This is a ‘homeshare’ SRT & is within the in-resident owners’ home - separately entranced & private for convenience/safety.

11–18 Sep

₹9,130 per night

Guest favourite

Guest suite in Chesapeake

4.97 out of 5 average rating, 235 reviews

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!

Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!

12–19 Jul

₹9,666 per night

Guest favourite

Guest house in Norfolk

4.98 out of 5 average rating, 553 reviews

Private Guesthouse, Ghent/Downtown near ODU, EVMS

Legally licensed and permitted with the City of Norfolk! We did it right here! European-style guesthouse between Ghent and the Heart of Downtown. Walking access to many restaurants and hotspots, and across from “The Tide” light rail, and YMCA, Chrysler Museum of Art, Granby St, Colley Ave, EVMS, Town Point Park! 15-min from the ocean. FREE PRIVATE PARKING: designated driveway parking spot; Kitchenette includes– cooktop, sink, microwave, coffee, fridge; Wifi, separate HVAC, bath, FREE laundry.

21–28 Oct

₹10,768 per night

Guest favourite

Farm stay in Cape Charles

5.0 out of 5 average rating, 331 reviews

Private Guesthouse on Secluded Waterfront Farm

Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to urban centers. Our twenty acre waterfront farm, which has plenty of nearby walking or biking, and a dock onto a secluded arm of Plantation Creek, an inlet of the Chesapeake Bay, is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

12–19 Oct

₹13,231 per night

Guest favourite

Guest suite in Chesapeake

4.95 out of 5 average rating, 479 reviews

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

3–10 Jan

₹9,507 per night

Guest favourite

Townhouse in Chesapeake

4.88 out of 5 average rating, 110 reviews

2BR-1.5 Bath Electric & Vibrant R&R Townhome

Listing description Kick back & relax in this calm, stylish space. 1600 sq ft stunning renovated & designed townhome! -Skip the traffic; 15 min drive to most of Hampton Roads, beaches; 3 mins from restaurants, groceries & more -Free parking -Optimal cleaning 100% disinfected space -2 bedrooms -Comfortable 2 Queen Beds & 1 Full Futon -1.5 baths with high end, modern finishes -Outdoor back private patio seating - Smart home features: keyless access cord + living room TV with roku

11–18 May

₹13,715 per night

Guest favourite

Townhouse in Chesapeake

4.9 out of 5 average rating, 101 reviews

Family friendly townhouse

A perfect place to stay when you can't be at home! Townhouse located in lovely family friendly neighborhood. Only a 20-30 min drive to NOB, Portsmouth Naval Shipyard and Oceana. Bright open kitchen with everything you need. Large living room with new comfortable couch and large Smart TV to hang out and watch tv. Privacy fenced back yard to sit and enjoy the evening or a morning cup of coffee. Large master bedroom with full bath and tiled shower. Washer and dryer in the home.

15–22 Sep

₹14,210 per night

Guest favourite

Guest house in Hampton

4.99 out of 5 average rating, 286 reviews

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. (Please also check out our additional property "The Water's Edge"). Sun, Se and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house is located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High speed fiber-optic wifi and cable with blue ray player provided.

16–23 Oct

₹11,229 per night

Guest favourite

Place to stay in Virginia Beach

4.99 out of 5 average rating, 114 reviews

Salty Willow-a “suite retreat” in the heart of VB!

We love welcoming people to our home in the heart of Virginia Beach! Come and go as you please in our guest suite with a separate entrance and privacy latches-no one will enter your space. We do our best to provide the comforts of home. -mini fridge -water filter -coffee bar -beach towels -folding chairs -beach blanket -sound machine -and more We want you to make yourself at home with us. Maybe we’ll enjoy a summer night together on the porch soon!

23 Feb – 2 Mar

₹8,639 per night

Guest favourite

Guest suite in Norfolk

4.93 out of 5 average rating, 216 reviews

Cobblestone street apartment with rooftop views!

Historic, Downtown area of Norfolk. Walking distance to shops, restaurants, museums, landmarks, parks, memorials, EVMS, & CHKD. This special residence is on the National Register of Historic Homes, includes a clawfoot tub & rooftop patio (no hold harm). This High Victorian Italian home was built in 1870, with a Mansard roof & features an ornamental cast iron veranda. John Cary Weston built this as a summer residence following the Civil War.

11–18 Nov

₹10,418 per night

Guest favourite

Home in Virginia Beach

4.9 out of 5 average rating, 207 reviews

Quilted Quarters by the Bay with Private Entrance

Enjoy beach life, hiking and biking near the Chesapeake Bay in a spacious fully furnished studio with a private entrance and private bath in a very safe and quiet neighborhood with one dedicated parking space as well. Five minute walk to the beach and First Landing State Park with hiking, biking, running trails, locally owned restaurants, bars, shops, breweries, grocery, pharmacy, farmer's market and yoga studio.

2–9 Jan

₹7,282 per night

Guest favourite

Guest house in Chesapeake

4.98 out of 5 average rating, 215 reviews

Beautiful and Chic, One Room Studio Apartment

Chic private apartment is located in a quiet neighborhood at the end of the peninsula were the Indian River flows into the Elizabeth River. Centrally located, we are nestled in the heart of Hampton roads with Virginia Beach 1 mile to the east and Norfolk 1 mile to the north. Twenty minutes from everywhere you'll want to go: the airport, the beach, multiple shopping centers and several universities.

31 Mar – 7 Apr

₹7,831 per night