Family-friendly holiday rentals in Williamsburg

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, 218 reviews

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

This beautiful 1 bed-1 bath unit is a cozy 400 sq.ft. and is located in the exclusive Kingsmill neighborhood. This first floor unit offers a king-size bed with a private patio that walks out onto the 9th Fairway of the River Course at Kingsmill. You'll enjoy the luxurious full bathroom with shower/tub combination and upgraded finishes. In the bedroom, you'll also find a computer desk, an over-sized sitting chair, a mini-fridge, a microwave, a Keurig coffee maker, and 50" Roku Smart TV w cable!

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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.

4.97 out of 5 average rating, 238 reviews

Stylish Creekside Cabin w/ HotTub, Parklike views.

Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

FamilyIndoor spacesView

4.94 out of 5 average rating, 154 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.

FamilyIndoor spacesTV

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, 170 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.

FamilyIndoor spacesCheck-in

4.96 out of 5 average rating, 114 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 on the outside, but inside it’s cozy, bohemian magic. Nestled on our little homestead, this is glamping at its finest: fresh air, feathered friends, and all the comforts of home (yes, we’re talking hot showers and AC). You can sip coffee with chickens, stargaze under wide-open skies, and maybe make friends with our crazy goats and obnoxious geese. Peaceful rural charm meets modern comfort, all just 15 minutes from Williamsburg.

FamilyIndoor spacesAir conditioning

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, 159 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.

FamilyKitchenAmenities

4.98 out of 5 average rating, 163 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.

Indoor spacesFamilyLaundry

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, 517 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.

KitchenIndoor spacesAmenities

5 out of 5 average rating, 196 reviews

Guesthouse in Gloucester

Summer Escape - Dock, Pool, Firepits, & Kayaks

A waterfront summer retreat tucked into 10 secluded wooded acres above Bland Creek, perfect for long days and relaxed evenings - Screened porch with water views and cool creek breezes - A Pool is available for rent for private use (open Memorial Day–Labor Day) - Dock, kayaks, fishing, firepits, and direct water access -Outdooring dining options and family-friendly - Immaculately clean and thoughtfully stocked for a seamless stay - Just 15 minutes from downtown Gloucester

FamilyIndoor spacesHeating

Guesthouse in Williamsburg

4.98 out of 5 average rating, 443 reviews

Freedom Cottage /King Bed-Jamestown/ Busch Gardens

The Freedom Cottage is a charming little 2 bedroom 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.

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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, 414 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.

KitchenIndoor spacesBathroom

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, 275 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.

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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

4.97 out of 5 average rating, 178 reviews

An aerial view depicts the guest suite, nestled among lush greenery, with a spacious swimming pool nearby. The main house, along with various outdoor amenities, is visible, showcasing well-maintained landscaping and open fields surrounding the property.

Guesthouse in Suffolk

Country Living Guest House (Upstairs/Downstairs)

KitchenIndoor spacesParks

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, 315 reviews

Historic Powhatan Resort- 2 bedroom condo!

Indoor spacesKitchenOutdoor spaces

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

KitchenFamilyPets

4.96 out of 5 average rating, 158 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

KitchenIndoor spacesTV

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.

FamilyIndoor spacesLaundry

4.95 out of 5 average rating, 111 reviews

A grand deck is viewed, featuring two white rocking chairs overlooking a vibrant sunset over the water. The sky is filled with shades of pink and orange, reflecting on the calm ocean surface. A dark wicker seating area is visible to the right.

Home in Buckroe Beach

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

Indoor spacesKitchenValue

4.98 out of 5 average rating, 174 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

FamilyKitchenDecor

4.81 out of 5 average rating, 27 reviews

1br Colonial in Williamsburg -Fun by Busch Gardens

KitchenIndoor spacesLocation

Family- and pet-friendly home rentals

5 out of 5 average rating, 106 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

FamilyIndoor spacesDecor

4.88 out of 5 average rating, 103 reviews

Williamsburg Retreat

FamilyIndoor spacesPets

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"

FamilyKitchenParking

4.86 out of 5 average rating, 345 reviews

Bamboo Bungalo Duplex Near Busch Gardens

FamilyIndoor spacesPets

4.8 out of 5 average rating, 109 reviews

A wooden cabin constructed from rich timber is showcased amidst a natural setting. The structure features large windows that allow for natural light and a welcoming porch with sturdy steps leading to the entryway.

Cabin in Williamsburg

Log Cabin - Williamsburg Pet-Friendly, Heated Pool

FamilyIndoor spacesSolo travel

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

FamilyIndoor spacesBathroom

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.

4.91 out of 5 average rating, 118 reviews

Cheerful 2 bedroom townhouse with fireplace

FamilyKitchenLong stay

4.83 out of 5 average rating, 617 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

Indoor spacesFamilyPets

Family-friendly home rentals with a pool

5 out of 5 average rating, 7 reviews

Look Here! Great value 2BDR at Powhatan Resort.

KitchenFamilyHot tub

4.99 out of 5 average rating, 220 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

Indoor spacesKitchenCheck-in

4.99 out of 5 average rating, 132 reviews

Home in Irvington

The Rosé Retreat: Pool-Screened Porch-RELAX

Indoor spacesKitchenView

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, 90 reviews

Lovely 2 Bedroom Condo in 4Diamond Historic Resort

FamilyIndoor spacesQuiet

5 out of 5 average rating, 128 reviews

A clear blue pool is framed by wooden decking and lush greenery. The inviting water reflects the sky, and the pool features a set of steps for easy access. Surrounding the pool are wooden railings, adding to the private feel of the outdoor space.

Apartment in Irvington

Pelican Place, Cozy Retreat | Pool | Walk to Tides

Indoor spacesFamilyPets

4.96 out of 5 average rating, 296 reviews

Tiny home in West Point

The Cozy Cottage At Grateful Meadows

KitchenIndoor spacesAir conditioning

4.95 out of 5 average rating, 141 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

KitchenFamilyQuiet

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.