Family-friendly vacation rentals in Williamsburg

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!

Indoor spacesFamilyLayout

4.99 out of 5 average rating, 221 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.

Indoor spacesKitchenBackyard

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.

Indoor spacesKitchenAccuracy

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 out of 5 average rating, 142 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.

Indoor spacesFamilyCleanliness

4.97 out of 5 average rating, 115 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.

Camper/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 spacesPets

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.

FamilyIndoor spacesValue

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.

KitchenIndoor spacesGrill

4.87 out of 5 average rating, 136 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!

Our river-side guest house has everything you will need to enjoy your getaway! Enjoy the river, dock, two kayaks, paddle board, canoe, large game room, portable fire pit, playground, basketball goal and large outdoor sitting area with a gas grill. Located 5-20 mins from the finest wedding venues, nearby wineries; less than an hour to Richmond & 25 minutes to Colonial Williamsburg. Only steps to numerous historic plantations & a few miles from the Virginia Capital bike & walking trail.

Indoor spacesFamilyValue

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.

Apartment in Williamsburg

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.

FamilyKitchenGetting around

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.

FamilyKitchenComfort

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.

Indoor spacesKitchenAccuracy

4.86 out of 5 average rating, 345 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.

Indoor spacesFamilyCondition

Popular amenities for Williamsburg family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a 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, 218 reviews

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

KitchenFamilyWalkability

Apartment in Williamsburg

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!

FamilyKitchenLong stay

Superhost

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.

Apartment in Williamsburg

4.86 out of 5 average rating, 231 reviews

Westgate Historic Williamsburg One Bedroom

Indoor spacesKitchenPool

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

KitchenFamilyWifi

5 out of 5 average rating, 196 reviews

Guesthouse in Gloucester

Summer Escape - Dock, Pool, Firepits, & Kayaks

Indoor spacesFamilyOutdoor spaces

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

KitchenFamilyOutdoor spaces

4.99 out of 5 average rating, 132 reviews

Home in Irvington

The Rosé Retreat: Pool-Screened Porch-RELAX

Indoor spacesKitchenCleanliness

Superhost

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

4.8 out of 5 average rating, 109 reviews

Log Cabin - Williamsburg Pet-Friendly, Heated Pool

Indoor spacesFamilySolo travel

Family-friendly home rentals with air conditioning

4.94 out of 5 average rating, 154 reviews

Home in Toano

Serenity Over 5 Acres: Historic Triangle Haven

Indoor spacesKitchenHeating

A bright guestroom is furnished with two double beds, each featuring a light-colored quilt. Nightstands with lamps are positioned beside the beds. A large window offers views of greenery, with soft curtains complementing the decor.

4.96 out of 5 average rating, 158 reviews

Comfy 1BR w pond view Kingsmill

FamilyIndoor spacesCondition

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, 169 reviews

Sarah's Creek Starlight

Indoor spacesFamilyAmenities

4.95 out of 5 average rating, 323 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

Indoor spacesKitchenNearby

4.99 out of 5 average rating, 198 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

Indoor spacesFamilyCleanliness

Guest favorite

The living area features a light grey sofa, two teal armchairs, and a wooden coffee table. A woven basket holds a soft throw. In the background, a kitchenette is visible, along with cabinets and appliances, illuminated by natural light from skylights.

4.95 out of 5 average rating, 150 reviews

2 Bedroom Stylish Kingsmill condo

KitchenIndoor spacesLayout

4.92 out of 5 average rating, 131 reviews

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

Indoor spacesKitchenHiking

5 out of 5 average rating, 186 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

FamilyIndoor spacesAccess

Family-friendly home rentals with Wifi

4.94 out of 5 average rating, 583 reviews

A rustic cabin is surrounded by lush trees, with a welcoming porch showcasing seating. The exterior features wooden panels and large windows, allowing natural light to fill the interior while maintaining privacy. A gravel path leads to the entrance, enhancing the natural landscape.

Guesthouse in Saluda

Wooded Cabin retreat on fresh water pond

KitchenFamilyCheckout

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 spacesWalkability

Guest favorite

4.88 out of 5 average rating, 103 reviews

Williamsburg Retreat

FamilyKitchenCondition

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"

FamilyIndoor spacesRiver

4.97 out of 5 average rating, 134 reviews

An open living area is presented, featuring a stone fireplace and a large flat-screen TV mounted on the wall. A dining table with four wooden chairs is set with decorative placemats. Relaxing furniture includes a brown leather sofa and a recliner, offering comfort and style.

Home in Gloucester Point

Amazing Gem! Riverfront, Location, Sunsets, Quite

FamilyKitchenValue

4.99 out of 5 average rating, 201 reviews

A panoramic view showcases the serene Rappahannock River, bordered by lush greenery and gentle coastal grass. The image captures the water's calm surface under a clear blue sky, with subtle clouds adding texture to the scene. A wooden boardwalk extends toward the water, enhancing accessibility.

Cottage in Urbanna

Little Dipper -private beach,Kayaks & paddleboards

FamilyIndoor spacesBeach

Home in Gloucester County

A wooden dock extends into the tranquil waters, bordered by smooth stones along the shore. Bright blue skies with scattered clouds enhance the natural beauty of the scene, inviting leisurely activities by the water.

4.96 out of 5 average rating, 112 reviews

York River | Chesapeake Bay Bliss: Fishing Retreat

Indoor spacesFamilyComfort