
Family-friendly vacation 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.

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.

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!

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.

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. You will also have the added convenience of having the host family on site. We do our best to provide the comforts of home. -fridge/freezer -beach essentials -toaster -coffee bar -extra essentials We want you to make yourself at home with us. Maybe we’ll enjoy a summer night together on the porch soon!

Modern Luxury Peace & Quiet.
Covered parking with EV Charger. With one acre fenced in yard. 1000+ sq ft Modern Second Floor Guest House apartment with separate private entrance attached to a 10,000+ sq ft Mansion on 3 acres in a very safe, quiet and private neighborhood. Free private parking. Minutes from restaurants, shopping centers, and a beautiful 30 minute drive to oceanfront. Free Netflix, High Speed WiFi, washer, dryer, full kitchen. With Keurig. Brand new Heat and Air Condition! Plus 2 dedicated parking spots.

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.

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 primary bedroom with private bathroom and shower. Washer and dryer in t

King Guest Suite - A Family Vacation Rental
Come enjoy a great stay in this beautiful private In-law suite, located in the heart of Chesapeake where you can get lost in nature, peruse the fare at a farmer's market, or picnic on the water's edge with your family. Just within 15 to 30 minutes from surrounding Naval bases, Virginia Beach Oceanfront and Downtown Norfolk. All you have to do us gas-up and unplug. We'll take it from there. Reserve your stay today and let your moments begin!

2 Bedroom Condo ONE Block from the Oceanfront
Come enjoy a Virginia Beach vacation ONE block from the oceanfront and boardwalk. Our 2 bedroom condo accommodates 4 adults and is also perfect for families. Bedroom 1 has a queen size bed and bedroom 2 has a king size bed. There is also a pull out sofa bed in the living room. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. There is plenty to do for the whole family.

Beautiful and Chic 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.

Cook's Country Escape - Cozy Retreat w/ Big Deck
Escape the everyday and enjoy this cozy countryside retreat! Nestled halfway between Virginia Beach and the Outer Banks, this home offers the charm of a cabin with the comforts of a full house. Perfect for families or friends, it’s a peaceful getaway from city life yet close to beaches, parks, and attractions. From the moment you arrive, you’ll feel the warmth and relaxation of a true country home.

Cozy Private Studio
Cozy, fully equipped, inviting studio located in the heart of Virginia Beach! Minutes from highway 64. Which gives easy access to anywhere in the Hampton Roads area. 15-20 minute drive to Virginia Beach Ocean front and convention center. 2 minutes from Regent University, CBN and founders in. Soccer complex, Stumpy lake golf course close by. Restaurants and shopping 5 minutes away.
Popular amenities for Chesapeake family-friendly rentals
Family-friendly home rentals with a hot tub

Horses-Views-Dog Friendly-4WD Area

Wooded Wonderland Miniature Golf Hot tub Pool

902C Coastal King Retreat Steps from Beach + Sauna

Hot Tub + Walk to Beach! Fully Updated + Spacious

Spring Hill Guest Cottage - Portsmouth

Wickline Cabin on Moon Creek

Comfortable 3 bedroom house with deck with hot tub

Cozy Cottage - NEW hot tub, dogs OK, fenced yard
Family- and pet-friendly home rentals

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

Quiet East Beach Bungalow, 1 block to beach!

Castaway 2 bed cottage by the beach

The Cozy Cottage Two Bedroom, King bed House

Lovely Ocean View Cottage

Perfect Getaway!

Airstream Farm Stay Cape Charles

The Nook
Family-friendly home rentals with a pool

Villa Positano

Oceanfront Gem VaB Studio Exceptional Views

Ocean & Bay Views - Local Family Owned & Operated

Oceanfront Studio: Boardwalk, Beach, & Pool Views

Country Comfort Close to the Beaches

Gorgeous Vacation House

Newly Built Apt Near Oceanfront

"Shangri-La", of Hampton, Virginia
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $171 CAD | $182 CAD | $185 CAD | $191 CAD | $206 CAD | $219 CAD | $235 CAD | $238 CAD | $201 CAD | $182 CAD | $178 CAD | $178 CAD |
| Avg. temp | 6 °C | 7 °C | 10 °C | 16 °C | 20 °C | 25 °C | 27 °C | 26 °C | 23 °C | 18 °C | 12 °C | 8 °C |
Quick stats about vacation rentals that are family-friendly in Chesapeake

Total vacation rentals
Explore 440 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at $27 CAD per night before taxes and fees

Verified guest reviews
Over 15,470 verified reviews to help you choose

Pet-friendly vacation rentals
Find 160 rentals that welcome pets

Vacation rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wifi availability
430 of Chesapeake vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesapeake rentals

4.7 Average rating
Chesapeake stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Chesapeake’s top spots, include Chrysler Museum of Art, Nauticus, and Cinema Cafe-Greenbrier Mall
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- Family-friendly rentals Virginia
- Family-friendly rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Buckroe Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Jamestown Settlement
- Grandview Beach
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- Kiptopeke Beach
- Outlook Beach
- Norfolk Botanical Garden
- Virginia Beach National Golf Club
- Ocean Breeze Waterpark
- Golden Horseshoe Golf Club
- Cape Charles Beachfront
- Chrysler Museum of Art
- Wilkins Beach
- James River Country Club
- Red Wing Lake Golf Course
- Little Creek Beach




