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.

1 of 1 pages1 / 1

Top Guest favourite

The front entrance features a ramp leading to a bright blue door surrounded by large windows. The white exterior of the house is complemented by landscaping with green shrubs and a sunny sky overhead, enhancing the welcoming appeal.

Cottage in Virginia Beach

4.97 out of 5 average rating, 220 reviews

The Seaglass Cottage by the Chesapeake Bay

The Seaglass Cottage by the Bay is located in the charming & beautiful neighborhood of Ocean Park just a quick 5-10 minutes stroll to the Chesapeake Bay beach. Our vintage beach house from the 1940’s has been fully remodeled and decorated in local art and beach décor. There are beautiful live oaks on the property and 3 private parking spaces for you and some first-come-first-serve street parking in front of the house. Easy load in with a ramp into the house and a mudroom for all your beach toys.

Indoor spacesKitchenNearby

Top Guest favourite

A tranquil beach scene is captured, featuring smooth sandy stretches bordered by green grass and gentle dunes. The horizon reveals a calm ocean meeting a partly cloudy sky, creating a serene atmosphere that invites relaxation and reflection.

Cottage in Norfolk

4.98 out of 5 average rating, 312 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

Escape the crowds and commercial beach resorts. At Courtyard Cottage, you'll enjoy the exact opposite—a peaceful beachfront retreat where a short walk over the sand dunes leads to a quiet, uncrowded beach, perfect for relaxing and unwinding. Proud Superhosts for over four years, we're dedicated to making your stay comfortable, relaxing, and memorable. The host, Richard, lives in a detached garage apartment on the property, allowing guests to enjoy complete privacy in their own accommodations.

FamilyKitchenParks

Top Guest favourite

The spacious kitchen features a large island with seating for six, modern appliances, and ample counter space. A bright window above the sink offers views of the surrounding landscape, while soft lighting complements the contemporary design. Light wood flooring enhances the welcoming atmosphere.

Farm stay in Cape Charles

5.0 out of 5 average rating, 430 reviews

Guesthouse at Vessel Farm & Winery, Waterfront

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 town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

Indoor spacesKitchenLong stay

Superhost

A couple relaxes on the deck of the sailboat, enjoying drinks against a vibrant sunset backdrop of pink and purple hues. Soft blankets and a cozy atmosphere are present, with the marina and boats gently reflected in the calm water.

Boat in Norfolk

4.91 out of 5 average rating, 140 reviews

Romantic Sailboat Experience + Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. The perfect stay begins by treating yourselves to dinner at the marina's seafood restaurant, then snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love rocking with the gentle sway of calm waters. Come enjoy a weekend aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

Indoor spacesFamilyHospitality

Top Guest favourite

A sandy beach stretches into the distance, bordered by gentle dunes and green grasses. A wooden walkway leads to the shore, where several figures can be seen walking. The calm ocean reflects the blue sky, dotted with fluffy white clouds.

Home in Virginia Beach

4.99 out of 5 average rating, 235 reviews

Play by the Bay 1 MIN TO WATER

LESS THAN 1 MIN WALK TO WATERS EDGE. Fantastic beach home with 3 bdrms, 3 baths, Living room-dining rm combo with vaulted ceilings, kitchen, TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill, Washer-dryer. Great water views while you are relaxing on the deck. Many amenities! Just bring your bathing suit. Our guests have all said they love this place! Very close to many wedding venues, restaurants, state park, oceanfront boardwalk is closeby, military bases, etc.

FamilyIndoor spacesCondition

Guest favourite

Large windows provide stunning views of the lake, reflecting vibrant colors of the sunset. A small potted plant sits on a table beside a white chair, while light from the setting sun casts a warm glow across the interior space.

Home in Norfolk

4.94 out of 5 average rating, 138 reviews

THE POINT! Private waterfront Oasis!

Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Bring your fishing poles!

Indoor spacesKitchenNearby

Guest favourite

A two-story townhome displays a modern exterior with gray and white siding. A welcoming front porch features a white railing and two entrance doors. A colorful flag adds a cheerful touch, while a privacy fence is visible in the background.

Townhouse in Virginia Beach

4.92 out of 5 average rating, 130 reviews

Beach Livin' by the Chesapeake Bay - VA Beach

Beach livin' just a few short blocks to the Chesapeake Bay, Beach & great restaurants.. Tastefully decorated - all the amenities. 6 person farmhouse table. Deck has table & chairs, grill. Privacy fenced backyard. Beachcart, chairs, towels, umbrella & sand toys. 2 queen beds & 2 bunk beds. Cozy livingrm w/loveseat, wicker chair, wicker swivel rocker, barstools, smart tv with basic cable. Base Rate includes 9% VA Beach occupancy tax and Lodging room tax

KitchenIndoor spacesComfort

Top Guest favourite

Home in Norfolk

4.93 out of 5 average rating, 157 reviews

The Cozy Beach House

We keep it simple here in this small, cozy, clean, and charming, home. House is great for 1 or 2 maybe 3 people. A 10 minute walk, to a public access, that takes you straight to the beach. Golf cart available for use . There are a few public parking spaces. 10 minutes to Norfolk International Airport. The Oceanview Pier is a great place to fish and have dinner and is only 3 miles away. Come and enjoy! There is also a NEW CASINO only 20 minutes away.

Indoor spacesKitchenDecor

Guest favourite

The living area is designed with a mix of modern furnishings and artwork. A comfortable sectional sofa and an accent chair surround a coffee table. Light streams in through a window, highlighting a TV and a decorative cabinet. Artwork adds a pop of color to the neutral walls.

Home in Norfolk

4.92 out of 5 average rating, 150 reviews

3BR Mid-Century Modern Home • Near Airport

Welcome to our beautifully updated 3-bed, 2-bath home in Norfolk. Featuring a spacious layout with cozy beds, it’s ideal for families or groups. Enjoy a gourmet kitchen, a huge dining space, Wi-Fi, a washer and dryer, and all the amenities needed for a relaxing stay. Located next to Norfolk Airport and the Botanic Gardens, you’ll have easy access to all of Hampton Roads. Book your extended getaway today!

FamilyIndoor spacesNearby

Top Guest favourite

A vibrant sunset is captured over the water, with shades of orange and pink blending into the horizon. A wooden dock stretches into the foreground, surrounded by evenly spaced posts that rise from the calm water's surface.

Guesthouse in Hampton

4.99 out of 5 average rating, 411 reviews

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. Sun, Sea and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house 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.

FamilyIndoor spacesView

Guest favourite

Townhouse in Chic's Beach

4.85 out of 5 average rating, 110 reviews

Chic’s Beach Oceanfront 3BR Home With Deck Views

🌊 Direct beachfront location at Chic’s Beach 🌅 Ocean views from all 3 levels 🏡 Spacious 3BR home sleeps up to 8 🛏️ King, 2 Queen beds + twin-over-full bunk 🌴 Multiple private decks for relaxing outdoors 🍳 Fully stocked kitchen for easy meals 🛋️ Open living area perfect for gathering 📶 Fast Wi-Fi + Smart TVs throughout 🧺 In-home washer and dryer 🚶 Walk to local dining and beach favorites

Indoor spacesFamilyAccuracy

Top Guest favourite

Guest suite in Chic's Beach

4.94 out of 5 average rating, 274 reviews

Enjoy your little slice of heaven in Chics Beach!

4-5 min walk to Chic's beach. Avoid the crowds and live with the locals! Surrounded by amazing restaurants, bars, coffee shops, and even an urban winery. We are a convenient 15 min ride from the tourist Oceanfront but you will have plenty to do in our relaxed beach town. This is a guest apartment attached to my home .The motto of Chic's Beach is "No Bad Days". Come see for yourself!

Indoor spacesKitchenParking