Family-friendly vacation rentals in Gloucester County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Gloucester County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.

Home in Gloucester Point

York River Vacation Home

This lovely, spacious waterfront home is located on the York River in Gloucester County Virginia. It is the perfect get away to enjoy the relaxing sounds and sights of nature. The views are spectacular! Keep an eye out for osprey and dolphins as you enjoy watching the sunrise and set over the water. There is plenty to do! Relax in the salt water pool overlooking the water, bring a pole & fish and crab right off of the private dock, or venture out on the kayaks. 16 ton boat lift, Jet ski lifts.

4.99 out of 5 average rating, 226 reviews

Top guest favorite

A spacious deck extends towards the waterfront, surrounded by lush trees. Lounge chairs and seating areas are positioned for relaxing views of the calm water. A sunroom is visible to the right, offering additional indoor space. The overall setting invites outdoor leisure and tranquility.

Home in Cobbs Creek

Blue Heron WaterSide

Blue Heron Waterside awaits you...Private Hot Tub and Pool!Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?

4.98 out of 5 average rating, 176 reviews

Top guest favorite

A serene beach area is depicted at sunset, with soft waves lapping against a sandy shore. The water reflects golden hues, and trees line the distant shoreline, creating a peaceful natural setting.

Barn in Cobbs Creek

The Barn at Pond Point - Riverfront Home

The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

4.95 out of 5 average rating, 147 reviews

Top guest favorite

A spacious living area features a large sectional sofa and an armchair with an ottoman. Natural light enters through multiple windows, illuminating the wood flooring. A smart TV is positioned near a console. A dining area with seating is visible in the background.

Home in Gloucester

Welcome to this Waterfront Home with Amazing Views

Welcome to our waterfront Air Bnb. Nestled along the Ware River, this unique property offers an unforgettable experience that combines comfort, luxury, and the most amazing sunsets. The open kitchen, living, and dining areas offer amazing views of the river. The interior is tastefully decorated with the perfect blend of modern elegance and coastal charm. Come and experience coastal living where the water becomes your playground and every moment is a celebration of nature's splendor.

4.98 out of 5 average rating, 114 reviews

Top guest favorite

A spacious wooden dock extends over the water, featuring four teal Adirondack chairs positioned for relaxation. Lush greenery surrounds the calm waterway, and a clear blue sky is visible above, creating a serene setting for enjoying nature.

Home in Gloucester

Severnly Pointe Cottage Waterfront Retreat

Relax with the whole family at the peaceful "Severnly Pointe" Cottage just off the Mobjack Bay. Surrounded by water on 3 sides and a private dock, enjoy secluded access to everything the water provides. Kayak, fish or just enjoy the rivah breeze on the spacious dock with friends. Launch your boat at the private concrete boat launch on the property. Home is well equipped and enjoys water views from all 4 bedrooms. Only 10 a minute boat ride to the “fishing haven” Mobjack bay.

4.9 out of 5 average rating, 114 reviews

Top guest favorite

A historic sign for Glebefield, established in 1795, is positioned among mature trees. Bright yellow flowers add a pop of color in the foreground, contrasting with the earthy tones of the surrounding greenery, creating a serene and inviting atmosphere.

Cottage in Gloucester Courthouse

Historic Ware River Cottage at Glebefield

Come visit this quiet and peaceful setting on the Ware River in historic Gloucester VA. The cottage sits on a 65 acre waterfront property. This fully updated cozy cottage is a great home base for exploring Williamsburg, Yorktown, Jamestown and Richmond. Pets are welcome with a small fee and pre-approval. There are serval buildings and gardens to enjoy so please take note of the picture captions for details on the cottage and other dependencies.

4.98 out of 5 average rating, 234 reviews

Top guest favorite

An aerial view captures the charming waterfront home positioned gracefully by the Piankatank River. The exterior features a well-maintained landscape with a pathway leading to the entrance and visible outdoor seating. The surrounding trees provide a lush backdrop and a sense of tranquility.

Home in Gloucester

Charming Waterfront Home on Piankatank River!

Amazing waterfront home on the Piankatank River in Gloucester, VA! This one level 1400sf cottage has 3 bedrooms, 2 full baths, a sun room with sweeping views, screened porch, living room with wood burning fireplace & large smart TV, fully stocked kitchen, waterside decks, a terrific fire pit, spacious dock with amazing sunsets AND sunrises, eagles overhead, kayaks and more! Want to bring your boat? There's a community boat ramp 1 minute away.

4.98 out of 5 average rating, 125 reviews

Top guest favorite

A serene waterscape is presented, highlighting the cottage set among lush trees. A dock extends into the water, flanked by boats, with soft ripples reflecting the clear blue sky. The tranquil environment suggests a peaceful retreat by the water's edge.

Cottage in Gloucester Point

Sarah's Creek Starlight

Beautifully remodeled 1930 Sears Starlight kit home. This cottage is located on the waters of Sarah's Creek, making it just a short drive from Historic Yorktown and Williamsburg. This space is fully furnished with a new kitchen, dining and living areas, 2 bedrooms with queen beds, 1 bedroom with a bunk and one bathroom. No matter what your stay is for you can look forward to the comfort, relaxation and beautiful views this cottage has to offer.

4.99 out of 5 average rating, 175 reviews

Guest favorite

A single-story brick house is surrounded by well-maintained landscaping, featuring a covered patio area with colorful seating. Vibrant flowering plants and a tidy lawn enhance the outdoor space, while a tree-lined background adds greenery to the setting.

Home in Gloucester

The Bee Goode House on Main Street

Welcome to the Bee Goode House! We want our future and returning guests to know of our diligence in sanitizing and cleaning every surface after each guest. Linens are fresh and clean, and there is plenty of private space with a large yard surrounding the house. Relax and enjoy Gloucester Main Street from a 1950's renovated home. From Mid Century Modern furniture and renovated retro appliances, you will be comfortable and hip in our home.

4.97 out of 5 average rating, 199 reviews

Top guest favorite

Guesthouse in Gloucester

Cozy Fall Retreat - Creek Views & Fire Pits

A cozy waterfront escape tucked into 10 wooded acres above Bland Creek. Perfect for crisp fall days and peaceful evenings. - Elevated screened porch with colorful water and wooded views - Creekside fire pits for crisp fall nights - Dock, kayaks, fishing, and direct water access - Outdoor dining and hammocks beneath the trees - Immaculately clean and thoughtfully stocked for a seamless stay - Just 15 minutes from downtown Gloucester

5.0 out of 5 average rating, 206 reviews

Top guest favorite

The exterior of the historic house is visible, featuring a red roof and white siding. A swing is situated on the lush green lawn, framed by trees. Flower beds add color along the path leading to the inviting porch and large windows of the home.

Farm stay in Gloucester

Historic Farmhouse. Peace & Quiet on 5 acres

Built in 1850 and lovingly restored to keep the original charm, come and enjoy all that Gloucester has to offer. Close to main attractions AND small town amenities. 30 minutes to Water Country, Busch Gardens, local wineries, Historic Colonial Williamsburg, Yorktown Battlefields. Within an hour of Richmond. Great central location. Gloucester offers local breweries, fresh seafood, great retail shops and dining.

4.93 out of 5 average rating, 136 reviews

Guest favorite

A serene river view is captured at sunset, showcasing vibrant hues of orange, pink, and purple across the sky. A wooden pier extends into the water, backed by silhouetted trees. The calm surface reflects the colorful sky, creating a tranquil atmosphere.

Guesthouse in Gloucester

Clay Bank River Front Cottage

Recently updated waterfront cottage 2 bedroom - 2 queen beds, a pull out sofa, 28 private acres on the York River in Gloucester, Va. Great remote getaway with a pool, kayaks and private pier for fishing/crabbing. Lightly traveled river. Access to Yorktown, Newport News, Williamsburg, Jamestown, Richmond, Norfolk, Urbanna. Shares the property with the main house where owner lives.

4.93 out of 5 average rating, 123 reviews