Family-friendly holiday rentals in Williamsburg

A bright living area features a light-colored couch with decorative pillows, complemented by a rustic trunk coffee table. A blue front door can be seen, inviting natural light into the space. Framed botanical prints are displayed on the walls, enhancing the cozy atmosphere.

4.98 out of 5 average rating, 218 reviews

Eclectic Bungalow 5 mins from Busch & Colonial Wbg

This cozy vintage home is centrally located, just 5 minutes from Colonial Williamsburg & 5 minutes from Busch Gardens. A beautiful blend of classic & modern, your home away from home boasts a large kitchen, full sized laundry, a bathroom with tub, a bedroom with queen bed and desk, a bedroom with two twin beds, & a flex living/bed room that can be closed off featuring a high-end memory foam queen sleeper sofa. Large fenced yard for outdoor fun, it’s the perfect place for your Williamsburg stay!

KitchenIndoor spacesHospitality

A charming Cape Cod home with a spacious front porch is surrounded by lush greenery and colorful flowers. The sloping roof features three dormer windows, while the well-maintained lawn provides an inviting entryway. The porch is equipped with seating and decorative accents.

4.83 out of 5 average rating, 294 reviews

Colonial Retreat

Enjoy a getaway in our 1940 Cape Cod home minutes from Colonial Williamsburg & Jamestown. Within biking distance to many attractions such as Williamsburg Winery, Jamestown Island & Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The house was refinished in 2021; you'll find an updated kitchen, smart TVs, large back patio & front porch. Please read the house rules before booking. No smoking. Need more space? Inquire about our other units

KitchenFamilyHeating

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, 171 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.

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4.99 out of 5 average rating, 223 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

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.

FamilyKitchenBathroom

A historic house is set amidst gentle greenery, featuring a white exterior with multiple chimneys and a welcoming porch. A white picket fence encircles the lush yard, enriched by tall trees and seasonal foliage, creating a serene and inviting environment.

5.0 out of 5 average rating, 144 reviews

History Art and Nature-110 Acres of Ancient Forest

WILLIAMSBURG AREA, SURRY, VA. CELEBRATE AMERICA'S 250TH by living in the historic family home of a Revolutionary War soldier! Lightwood Forest is a beautiful historic house nestled in 110 acres of private woodland preserve. Surround yourself with history, antiques, art and nature, and over two miles of private hiking trails. Lightwood Forest is in rural Surry County, on the south side of the James River, a short, free car ferry ride from Williamsburg and Jamestown, which runs 24/7, all year.

KitchenFamilyCleanliness

A spacious colonial-style home is set on manicured grounds, surrounded by trees. The exterior features a welcoming covered porch, large front windows, and well-maintained landscaping, creating an inviting first impression for guests.

4.94 out of 5 average rating, 222 reviews

The Williamsburg Retreat- Gorgeous Private Acreage

Stunningly manicured and spacious custom built colonial on 6 private acres. - Specializing in large multigenerational family vacations, business and church retreats, and discerning private getaways. Perfect for those desiring comfort, style and space. - Massive covered deck with fire table and outside dinning. Start your day here with coffee and finish it with your favorite wine. -Collect fresh eggs and let the kids run!!! -17 min. to top Williamsburg attractions. -10 min. to outlet mall ;)

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5.0 out of 5 average rating, 110 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

Important: NO 3RD PARTY RES. Tiny Red Barn is a labor of love built by us for you on the Diascund Reservoir with water views, wooded trails and sunsets. We feel like we're on vacation every day of the year and look forward to sharing our 26 acres with you. Heavily wooded land with rolling trails, birds, deer, squirrels, turtles, chickens, mini donkeys and bees. A large amount of our property sits on the Diascund Reservoir which provides a whole other side of nature. Opened April 1, 2021.

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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, 160 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.

Indoor spacesFamilyHospitality

4.97 out of 5 average rating, 119 reviews

The interior of the RV features a vibrant green kitchen with a countertop, oven, and microwave. A cozy dining area with a table and benches is visible. Colorful artwork and decorative elements adorn the walls, while warm lighting from unique fixtures adds ambiance.

Campervan/RV in Toano

Boho Glam Farm Stay-Right Outside Williamsburg

Step into the best of both worlds—our 1999 RV may look vintage outside, but inside it’s cozy, bohemian magic. Nestled on our little homestead, this is glamping with fresh air, feathered friends, and all the comforts of home (yes, we're talking hot showers & AC). Sip coffee while the occasional rogue chicken wanders by, stargaze under wide-open skies, and meet our crazy goats and obnoxious geese. Peaceful farm charm meets modern comfort, just 15 minutes from Williamsburg.

KitchenIndoor spacesQuiet

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, 417 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.

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Cottage in Gloucester Point

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.

4.99 out of 5 average rating, 172 reviews

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.

FamilyIndoor spacesOutdoor spaces

4.86 out of 5 average rating, 348 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.

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Popular amenities for Williamsburg family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.86 out of 5 average rating, 231 reviews

Westgate Historic Williamsburg One Bedroom

KitchenIndoor spacesBackyard

4.98 out of 5 average rating, 175 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

FamilyIndoor spacesRiver

The image showcases a row of two-story condos with light-colored exteriors set against a vibrant green lawn. Neatly trimmed bushes and small trees add to the landscape, which is touched by sunshine and soft clouds, creating an inviting environment.

4.91 out of 5 average rating, 316 reviews

Historic Powhatan Resort- 2 bedroom condo!

Indoor spacesFamilyParking

Guesthouse in Gloucester County

A winding gravel pathway is illuminated by soft lighting, bordered by lush greenery. String lights are hung above, casting a warm glow over the area, which is surrounded by trees and plantings. A staircase leads to an elevated area in the background.

4.98 out of 5 average rating, 241 reviews

Stylish Creekside Cabin w/ HotTub, Parklike views.

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The exterior of a historic brick building is shown, featuring a classic symmetrical design with multiple windows and a central entrance. A winding pathway leads through a landscaped yard, framed by trees and flower beds, suggesting a serene outdoor environment.

4.86 out of 5 average rating, 124 reviews

Best Resort/$$$ for Colonial Wburg & Busch Gardens

Indoor spacesKitchenSleep quality

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.

4.89 out of 5 average rating, 215 reviews

Fun Space close to Busch and Colonial w/ Hot Tub

KitchenFamilyValue

4.96 out of 5 average rating, 162 reviews

An aerial view captures the spacious backyard featuring a rectangular swimming pool surrounded by a concrete deck. Lounge chairs are placed by the poolside, with a well-maintained lawn and shrubs in the background. The two-story cottage is shown with a screened porch and a shaded area nearby.

Cottage in Chesapeake

The Cottage @ Captain Genes - Secluded Waterfront

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Two figures in historical military uniforms with distinctive red coats are shown standing together. The background features a building with a bright sky, while a British flag is visible nearby, suggesting a reenactment or historical event.

4.72 out of 5 average rating, 147 reviews

Great family vacation resort condo. Sleeps 12.

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Family- and pet-friendly home rentals

A tranquil lakeside scene captures two individuals on paddleboards gliding across calm water. Sandy shores are lined with chairs, offering a peaceful spot to relax. In the background, a spacious building features a wraparound deck, providing views of the serene landscape.

4.97 out of 5 average rating, 119 reviews

Walk to beach lovely 2/2 in "Kingsmill on James"

Indoor spacesKitchenCleanliness

4.98 out of 5 average rating, 167 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

Indoor spacesFamilyTV

4.95 out of 5 average rating, 144 reviews

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

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4.88 out of 5 average rating, 104 reviews

Williamsburg Retreat

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Townhouse in Williamsburg

A cozy living area is framed by an arched entryway, featuring a mix of seating options including a dark armchair and a spacious sofa. A coffee table made of natural wood occupies the center, while a television is mounted above a fireplace. Soft light filters through the windows.

4.89 out of 5 average rating, 122 reviews

Cheerful 2 bedroom townhouse with fireplace

FamilyKitchenSleep quality

4.86 out of 5 average rating, 138 reviews

A wooden dock extends into calm waters, reflecting a soft sunset with pastel hues. A covered boat slip is positioned at the end of the dock, framed by the serene landscape of trees on the horizon.

Home in Charles City

Chickahominy Riverside Guest Home By Williamsburg!

KitchenIndoor spacesLocation

Cottage in Gloucester Courthouse

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.

4.98 out of 5 average rating, 234 reviews

Historic Ware River Cottage at Glebefield

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4.83 out of 5 average rating, 618 reviews

A shaded porch area is featured, supported by white columns with a wooden ceiling above. A round table surrounded by four white chairs is visible on the deck. A blue potted plant adds a touch of greenery, enhancing the inviting outdoor space.

Cottage in Williamsburg

The Colonial Cottage

KitchenIndoor spacesHiking

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 201 reviews

Guesthouse in Gloucester

Cozy Fall Retreat - Creek Views & Fire Pits

FamilyIndoor spacesLaundry

4.91 out of 5 average rating, 138 reviews

Home in Hampton

4BD home w/ game room & pool near Langley & PTC!

FamilyKitchenTV

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, 85 reviews

Cozy 2BR Condo in Williamsburg

Indoor spacesKitchenSleep quality

A sweeping view of a lush green golf course is presented, featuring gently curving pathways and sand traps. Tall trees provide shade along the course, and a few golfers are visible in the distance, contributing to the serene landscape.

4.93 out of 5 average rating, 92 reviews

Lovely 2 Bedroom Condo in 4Diamond Historic Resort

Indoor spacesKitchenAir conditioning

4.93 out of 5 average rating, 28 reviews

WaterVue at Kingsmill

KitchenIndoor spacesWalkability

4.98 out of 5 average rating, 41 reviews

3 Bed, 3 Bath Sleeps 8 in Kingsmill

KitchenFamilyNearby

4.93 out of 5 average rating, 60 reviews

Home in Lanexa

America's 250 Getaway | Pool | Busch Gdns | Wmbg

KitchenFamilyBarbecue

A spacious sleeping area features a large wooden headboard and crisp white bedding, complemented by a dark green bed skirt. Light filters through a nearby window, adorned with decorative curtains, while a bedside lamp provides additional illumination.