Family-friendly vacation rentals in Williamsburg

4.95 out of 5 average rating, 146 reviews

Home in Toano

Serenity Over 5 Acres: Historic Triangle Haven

*4500 sq.ft. fully furnished house w/ 4 bedrooms & loft. *Includes all the amenities you need to enjoy a peaceful stay. * Unwind w/ friends & family in this modern retreat nestled on 5 acres in the woods w/ waterfront view & a fire pit. *You’ll enjoy the secluded area & yet be close to the bustle & hustle of what Williamsburg can offer. *Only 15-20 minutes to major attractions such as, Colonial Williamsburg, Bush Gardens, Jamestown, Yorktown, outlet mall. *Master bathroom only has a bath tub.

Guesthouse in Gloucester Point

A warm living area is captured, featuring a comfortable leather couch and a cozy yellow chair. A bottle of wine and two glasses are placed on the counter next to a sign inviting guests, while soft lighting creates a welcoming ambiance.

4.94 out of 5 average rating, 152 reviews

BlueBird Nest

Keep it simple at this peaceful and centrally-located oasis, tucked away in coastal Virginia. Our newly renovated 1BR/1BA barn apartment on 3 acres is ideal for those who want to live like a local. We are 3 miles from the heart of the American Revolution in Yorktown, and Yorktown Beach, and a short drive to area attractions in the Historic Triangle. Unwind after a day of exploring with a glass of wine on the balcony or enjoy the firepit and the view. This is an upstairs apartment with stairs.

The exterior of the house is illuminated by warm string lights, showcasing a spacious two-story structure. Adirondack chairs surround a central fire pit on a gravel patio, providing a cozy gathering area against a backdrop of tree line.

4.99 out of 5 average rating, 160 reviews

Cheerful 3-bedroom house with parking on premises

Have fun with the whole family at this cozy place. Conveniently located 2 minutes from the Great Wolf Lodge and 10 minutes from Busch Gardens, Colonial Williamsburg, the College of William and Mary, and several parks, this three-bedroom, three baths, big-basement stand alone house lets you explore “the Burg” hassle-free and recharge in a restful space on the back of the Waller Mill reservoir woods. The yard features beautiful landscaping, a large fire pit with solo stove & cozy backyard lights.

4.94 out of 5 average rating, 126 reviews

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

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!

4.86 out of 5 average rating, 323 reviews

Bamboo Bungalo Duplex Near Busch Gardens

Find your home away from home when visiting historic Williamsburg. It feels very private here nestled amongst the bamboo and trees. This is a great location for families with children! We are within 5 minutes of Bush Gardens and Water Country for great family fun outings! For history buffs, we are 7 minutes from Colonial Williamsburg, 15 minutes from Jamestown Settlement and 20 minutes from Yorktown Battlefields. Enhance your stay with a relaxing herbal massage at the on site massage studio!

Farm stay in Charles City

The exterior of a large black barn is shown under a clear blue sky. Two wooden doors are open, revealing a welcoming entrance. Flower pots are arranged along the path, while two wooden chairs are positioned in front, inviting relaxation amidst a tranquil rural setting.

4.99 out of 5 average rating, 151 reviews

Lovely space above barn on a working farm!

Getaway to the country!! Suitable for a 4 adults or families of 5. Wake up to beautiful sunrises. Spend a peaceful day surrounded by farm and wild animals. Enjoy the dark night sky lit with millions of stars after watching the sunset. Above our barn is a two bedroom, one bath living space with a living area open to a kitchen fit for every cook!! Located near Williamsburg, Jamestown and Yorktown, Busch Gardens and Water Country, the Virginia Capitol Trail and 5,217 acre wildlife refuge.

4.97 out of 5 average rating, 156 reviews

A red kayak rests at the edge of the serene reservoir, surrounded by trees that frame the waterway. The calm surface reflects the clear blue sky and soft ripples created by a gentle breeze, ensuring a tranquil outdoor experience.

Cottage in Lanexa

TooFine Lakehouse, pet friendly waterfront cottage

Cute & cozy (tiny) waterfront cottage nestled in a pine forest. Situated on an almost 3 acre point on the Diascund Reservoir this is THE perfect spot to get away from it all & still be in the middle of everything! Options abound - fishing from the dock, bird watching, canoeing, roasting marshmallows around the fire pit, swinging in the hammocks, napping on the screened in porch, grilling on the patio, reading in the loft, playing games (inside & out), or just chill & feel the vibe.

4.95 out of 5 average rating, 222 reviews

The interior of the tiny cabin showcases a unique staircase leading to a lofted sleeping area. Natural wood elements are highlighted throughout, with a clear roof allowing natural light to fill the space. A doorway opens to the outdoors, enhancing the cabin's connection to nature.

Tiny home in Diggs

Stargazer Tiny Cabin

(Winter: Stargazer has a diesel heater and a woodstove but is not insulated. The cabin can be kept quite warm into the low 30's if these heaters are running. Below freezing may freeze pipes, message for info) Rustic off grid tiny cabin tucked in the trees on the back side of a large field. The cabin has solar, kitchenette, shower, composting bathroom, heat, and Wifi! Enjoy being immersed in nature while staying comfortable in a quirky cabin built from local and reclaimed materials.

Superhost

The exterior of a cozy apartment is depicted, featuring a white facade with green shutters. A small porch is visible, accompanied by a sign indicating the apartment's name. Lush greenery and floral plants frame the entrance, while a gravel pathway leads to the door.

4.83 out of 5 average rating, 503 reviews

The Nook

Enjoy a getaway in this cozy 1 bedroom apartment attached to a classic 1940s Cape Cod home minutes from Colonial Williamsburg and Jamestown. You'll be within biking distance to many local attractions such as Williamsburg Winery, Jamestown Island, Jamestown Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The Nook was completely refinished in 2020. Need more space or traveling with a group? Inquire about our other units.

Guesthouse in Williamsburg

4.98 out of 5 average rating, 428 reviews

Freedom Cottage /King Bed-Jamestown/ Busch Gardens

The Freedom Cottage is a charming little cottage comfortable for four, can fit 5 with the sofa bed. You're minutes away from Freedom Park, The Premium Outlets, Jamestown Settlement and 15 minutes from Colonial Williamsburg, Busch Gardens and Water Country. The Williamsburg Winery is also well within reach of our home! Our place offers maximum utility and privacy! We ensure to sanitize every surface, wash every towel and replace every sheet after each guest.

Farm stay in Williamsburg

A lush field is filled with blooming yellow flowers under a clear blue sky. In the background, a red barn is situated near a fence, surrounded by trees that provide a natural border to the landscape.

4.97 out of 5 average rating, 402 reviews

3 BR Cottage on Mallardee Farm in Williamsburg

Enjoy all the comforts of home during your Williamsburg vacation at Mallardee Farm! Allow us to make our home, your home while you explore all of Williamsburg’s attractions-just a 15 minute drive away! You’ll find that Mallardee Farm will serve as its own attraction with our friendly, rescued farm pets, walking trails through the 57 acre property, complimentary fishing poles, canoe, row boat & kayaks to use on our 7 acre pond. Covid-19 precautions followed.

A single-story home is positioned on a grassy lot, surrounded by trees and bushes. A wooden staircase leads to the front porch, which is flanked by red shutters on the windows. The roof is gently pitched, and a clear blue sky with scattered clouds is visible above.

4.97 out of 5 average rating, 264 reviews

Casita on the Corner

The Casita is a cozy 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. The area is rich with historical sites. Be sure to visit Colonial Williamsburg, Jamestown and Yorktown. There is a shopping center with a Grocery store and restaurants within walking distance from the property.

Popular amenities for Williamsburg family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

Superhost

An aerial view of the property reveals a spacious backyard featuring a swimming pool surrounded by lounge chairs and inflatable pool toys. Lush greenery encircles the area, enhancing the sense of privacy, and the house is seen with its inviting deck and patio area.

Home in Portsmouth

4.92 out of 5 average rating, 161 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

A cozy bedroom features a king-size bed with crisp white linens and decorative pillows. A large window offers a view of a green space beyond, with a sitting area including a chair and small table. A 50" TV and coffee station are positioned on a wooden dresser.

4.94 out of 5 average rating, 201 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

4.99 out of 5 average rating, 211 reviews

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

A resort pool area is depicted, featuring a vibrant blue swimming pool surrounded by lounge chairs. The brick building in the background is characterized by rows of windows and a variety of green umbrellas, set against a clear blue sky.

4.87 out of 5 average rating, 215 reviews

Westgate Historic Williamsburg One Bedroom

Superhost

Camper/RV in White Stone

4.88 out of 5 average rating, 141 reviews

“Old Smokey”A cozy, single bedroom, unique getaway

4.96 out of 5 average rating, 399 reviews

An aerial view of a two-story home with a red roof, surrounded by lush green lawns. A sparkling pool is situated in the backyard, accompanied by lounge chairs, a patio area, and a gazebo. The property features a well-maintained outdoor space with nearby landscaping.

Apartment in Hampton

"Shangri-La", of Hampton, Virginia

4.96 out of 5 average rating, 291 reviews

A cozy cottage stands amidst lush green trees, showcasing a welcoming front porch with a circular doormat. Large windows allow natural light to filter in, complemented by the inviting wooden door, creating a harmonious blend with the surrounding forest.

Tiny home in West Point

The Cozy Cottage At Grateful Meadows

4.92 out of 5 average rating, 142 reviews

Colonial Williamsburg Spacious 4 Bedroom Suite!

Family-friendly home rentals with a hot tub

The historic manor house features elegant red brick construction with multiple windows and a central entrance. Lush greenery surrounds the building, including manicured lawns and vibrant shrubs, creating a serene outdoor environment. Two prominent chimneys rise from the rooftop, complementing the classic architecture.

4.91 out of 5 average rating, 45 reviews

2 Bedroom@Historic Powhatan Resort *Indoor Pool!*

A row of well-maintained two-story condos is set against a bright blue sky. Neatly trimmed hedges and vibrant flowering shrubs enhance the front landscaping, providing a welcoming appearance. The buildings feature light-colored siding and gabled roofs, creating a charming residential atmosphere.

4.9 out of 5 average rating, 157 reviews

Historic Powhatan Resort- 2 bedroom condo!

4.98 out of 5 average rating, 168 reviews

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

The image depicts a Colonial-style resort building featuring two sections with light blue and gray siding. Lush greenery surrounds the property, with well-maintained landscaping visible. A pathway leads to the entrance, enhancing accessibility to the inviting façade.

5 out of 5 average rating, 20 reviews

Kingsgate 2BR w/ Kitchen

A spacious condo building is shown, featuring multiple balconies and a mix of large windows. The exterior is painted in neutral tones, complemented by maroon shutters. A paved walkway meanders through a snow-dusted lawn, leading to the entrance of the building.

5 out of 5 average rating, 6 reviews

Wyndham Governor's Green (3 BD Deluxe)

An aerial view showcases the resort's well-planned amenities, including swimming pools, tennis courts, and a miniature golf course. Lounge chairs line the pool area, and landscaped green spaces surround the facilities, providing a welcoming environment for relaxation and recreation.

4.95 out of 5 average rating, 22 reviews

Family-friendly 2BR/2BA condo w/balcony-Kingsgate

A large outdoor swimming pool is surrounded by lounge areas and wooden picnic tables. Sun umbrellas in vibrant colors are positioned along the poolside. Clear blue skies create a bright backdrop, enhancing the inviting atmosphere of the resort area.

5 out of 5 average rating, 11 reviews

Wyndham Kingsgate (3 BD LO)

Guest suite in Williamsburg

A spacious recreational area is highlighted by a large pool table at the center. A bar area with high stools complements the setup. The walls are decorated with framed photographs, and soft lighting enhances the inviting ambiance. A coffee station is visible in the background.

4.9 out of 5 average rating, 209 reviews

Fun Space close to Busch and Colonial w/ Hot Tub

Family-friendly home rentals with air conditioning

5 out of 5 average rating, 101 reviews

The image displays The Tiny Red Barn, featuring white rocking chairs on a welcoming porch. Lush green grass surrounds the entrance, while trees create a serene woodland backdrop. To the right, a wooden dock extends into the calm waters of the Diascund Reservoir, with an American flag gently waving.

Farm stay in Lanexa

Tiny Red Barn on The Reservoir-Near Williamsburg

4.95 out of 5 average rating, 309 reviews

The kitchen features modern granite countertops and stainless steel appliances, including a cooktop and oven. An island with seating is complemented by pendant lighting. A decorative sign that reads 'EAT' and a warm color scheme enhance the inviting atmosphere, with an open layout connecting to the dining area.

Home in Yorktown

Modern-farmhouse Retreat

4.99 out of 5 average rating, 184 reviews

An open-concept living area features a spacious sectional sofa and a large TV mounted on the wall. The kitchen island, with seating for four, is equipped with modern appliances and stylish finishes, providing a clean and functional space for cooking and gathering.

Home in Gloucester Point

Pointe Haven near Historic Yorktown

A charming exterior view of the home is presented, showcasing a well-maintained yard surrounded by a picket fence. A welcoming screened-in front porch is visible, complemented by lush greenery and landscaping. An American flag adorns the entrance, indicating a family-friendly atmosphere.

4.88 out of 5 average rating, 112 reviews

Charming 2/1 home close to everything!

A serene landscape captures a sunset over the James River, with vibrant hues of orange and pink reflecting on the water. Silhouettes of trees frame the view, and a gently sloping green lawn leads toward the riverbank, enhancing the tranquil atmosphere.

4.94 out of 5 average rating, 145 reviews

Luxury Riverfront Condo w/ sunrise & sunset views

5 out of 5 average rating, 175 reviews

A serene cottage, surrounded by lush greenery, features a welcoming front porch with chairs and warm lighting. A gravel pathway leads to the entrance, highlighting the harmony between the home and its natural surroundings.

Farm stay in Smithfield

Cozy Farm Cottage with Horses, Fire Pit, & Trails

A spacious living area is showcased, featuring comfortable seating arrangements including a dark sofa and accent chairs. Natural light is welcomed through large glass doors leading to a balcony, with views of the lush surroundings. A fireplace and modern decor enhance the warm ambience.

4.92 out of 5 average rating, 75 reviews

Cozy 2BR Condo in Williamsburg