Family-friendly vacation rentals in Orange County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Orange County

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

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Guest favorite

The entryway is adorned with a festive wreath hanging on the door. A decorated sign reading 'Christmas' is positioned next to the door, accompanied by a potted plant and two decorative planters featuring seasonal foliage.

Home in Orange

4.84 out of 5 average rating, 285 reviews

Atlast-The Farmhouse

Don't let the exterior fool you, this brick home is decorated in Farmhouse Style, 1 mile from Historic Montpelier, 3 miles from Grelan Nursery, Orange, Willow Grove Inn and Woodberry Forest School. Across from a 30 acre farm. Gaze out the window at the horses and cattle, take a hike on a nearby trail or visit the many wineries in the area. Close to Charlottesville( 30 miles) Culpeper (20 miles) 1 and a half hours to DC. 20 minutes to HITS Horse show, Culpeper. Woodbrook Winery around the corner

The farm-style house features a modern design with light-coloured siding and large windows, allowing natural light to permeate the space. A cylindrical silo adjoins the structure, creating unique architectural interest. The grassy expanse surrounding the home offers a serene, open landscape.

Farm stay in Rapidan

4.85 out of 5 average rating, 131 reviews

Iconic Virginia Farmhouse with Furnished Silo

This beautiful house is the culmination of eight friends’ vision for an ecological and architectural experience. Set on a picturesque 33-acre grassfed cattle farm, this 4 bedroom, 3 loft, 2.5 bath dwelling is ideal for family get-togethers and intimate reunions with old friends. Many Blue Ridge Mountain sunsets have been celebrated from the open air balcony. Due to the number of staircases and separated rooms, the property is not ideal for folks with toddlers or those with mobility limitations.

Superhost

The image captures a serene outdoor setting with lush greenery surrounding a quaint blue cottage. Flowering plants border a neatly maintained lawn that leads to the distant tree line, creating a tranquil atmosphere. The cottage features a small deck with a railing, enhancing the natural landscape.

Guesthouse in Orange

4.84 out of 5 average rating, 80 reviews

Romantic Cottage Tiny House for 2!

Quaint studio Getaway suite set on the historical grounds of Greenock Manor. This Tiny House is only 5minutes drive from MontPelier in the heart of the wine country. Perfect for a couple or single person, the bedroom has an open plan kitchenette for self catering. Fridge, microwave, coffee machine, toaster and dishes are available. Ideal for hikers wanting to visit Shenandoah. Staff parking is behind the Tiny House but the front has views of the farmlands and forest. Enjoy our giant chess game

Superhost

A spacious wooden dock extends over the calm lake waters, featuring two lounge chairs positioned for relaxation. A small slide is visible, with fishing rods set up in the background. The surrounding greenery and clear blue sky create a serene waterfront setting.

Chalet in Mineral

4.72 out of 5 average rating, 280 reviews

Private Lake Anna Waterfront Chalet w/dock/beach!

Your cozy lakefront chalet is steps away from deep water and fun adventure. With sandy beach, fire pit, fabulous dock area, hammock, canoe, kayaks, and SUP, you will enjoy your lake vacation. Room to bring a boat and/or jet skis w/ community boat launch. High speed Internet, swingset, on a large private lot with woods between neighbors. Large deck overlooking lake with gas grill. The property has 250' of prime main lake frontage with fishing, dining, and sunbathing on dock. Pet friendly!

Top guest favorite

The entrance features double wooden doors that open to a welcoming interior. A 'hello' mat is placed on the threshold, and two stylish chairs are positioned on the balcony above, inviting guests to enjoy the view. Lush plants accentuate both sides of the entrance.

Apartment in Somerset

4.98 out of 5 average rating, 178 reviews

Cozy Farm Apt near Cville•wineries, mt. views

Come experience a relaxing getaway on our family’s dairy farm! Set in beautiful Orange County, We are close enough to Charlottesville (25 min) to fulfill all your shopping and eating needs, but have the privacy, calm and tranquility of the country, with beautiful majestic mountain views! This is a wonderful location for exploring all of wine country, unwinding from the hustle of busy life, and then taking in the sunset in this quiet country setting with rolling hills as your backdrop!

Superhost

A charming guest cottage is nestled among lush green landscaping. The structure features a metal roof and a porch with simple white railings. Tall trees provide shade, contributing to the serene atmosphere of the surrounding countryside.

Cottage in Madison

4.92 out of 5 average rating, 159 reviews

Charming Guest Cottage at Winery

Early Mountain Vineyards' charming Guest Cottage, nestled next to our front block of grapevines and below our historic hilltop barn, offers breath-taking views of the Blue Ridge Mountains and a serene place to watch the sunset while sipping wine. Only short distance to our Tasting Room - open 5 days a week, Thursday - Monday. We recommend a reservation in advance - this can be made via our website, Early Mountain Vineyards, or by calling our winery directly.

The Ordinary is surrounded by a spacious lawn, framed by trees and greenery. A small outbuilding is visible to the left, while the house features a welcoming porch and a pitched roof. Natural light brightens the exterior, emphasizing its classic Virginia charm.

Home in Barboursville

4.94 out of 5 average rating, 130 reviews

Historic 1790 House Near Charlottesville

Originally a tavern built 1790 in the "Hall and Chamber" style found in Williamsburg, the Ordinary sits 6/10 mile off main road--no other house in sight. Set among 650 acres in conservation easement; solar energy; generator in event of power outage; outdoor fire pit; 2 great fireplaces; wood provided by owner. The house is over 200 years old with narrow, steep steps and may not be suitable for children and persons with mobility issues.

Guest favorite

A restored two-story home features a light gray exterior with blue shutters and a large front porch. Lush foliage surrounds the walkway, which is composed of natural stone. Several windows allow ample light, and hanging plants add a touch of greenery to the entrance.

Home in Orange

4.98 out of 5 average rating, 122 reviews

Monrovia on Main

Monrovia on Main is a beautifully restored gem built in 1904. Guests have use of the entire 3,400 square foot, 5 bedroom home with 3 updated full baths. Enjoy a private backyard or front porch for morning coffee or evening drinks. Walking distance to an array of shops & restaurants in downtown Orange. The home is located near Montpelier, Woodberry Forest as well as Barboursville Vineyards.

Guest favorite

A modern kitchen features white cabinetry and stainless steel appliances. A spacious island with a marble countertop is surrounded by wooden stools. Natural light enters from a window above the sink, while a cozy seating area is visible in the background.

Home in Aroda

4.9 out of 5 average rating, 116 reviews

The Nest on Hawks Ridge

The Nest on Hawks Ridge is in the heart of all you want to do in Central Virginia! Newlyweds to families, everyone will love it here! The peace and quiet of the country, or the excitement of exploring new and different places all await you! Check out our Guidebook for local attractions, restaurants, nightlife and sightseeing. Enjoy the serenity of the country! Follow us: @nestonhawksridge

Guest favorite

The Servants' Cottage, built in 1856, is showcased with a classic white exterior and a metal roof. Surrounded by well-maintained grass and shrubs, it is set against a backdrop of trees and open fields. Natural light casts gentle shadows on the lawn.

Cottage in Gordonsville

4.85 out of 5 average rating, 157 reviews

Quaint Cottage - Wolftrap Farm (Horse neighbors)

From the large covered patio of this little cottage, you can watch the horses, see our largest pond, eat your meals if you choose, and marvel at the beauty of nature. You can also book our hot tub patio, swim in our creek, fish in our ponds, hike our many miles of farm roads and woodland trails, use our Game Barn, and sip wine as you watch the sun set behind the mountains.

A charming two-story guesthouse is presented with a stone chimney and a rustic red roof. The exterior features a mix of light-colored siding and blue accents around the windows. A well-maintained lawn with shrubs enhances the inviting atmosphere.

Guest suite in Madison

4.83 out of 5 average rating, 213 reviews

Farmette in Madison – Madison, VA

The Wolftown Farmette has a cozy fireplace, outdoor fire pit, a big front porch, two large bedrooms with two king size beds, a long bath tub and separate shower, all for you to enjoy after a day of hiking or vineyard tours. Come see us in Madison County! We are 3 minutes from Early Mountain Vineyard and 10 minutes from the Shenandoah National Park Graves Mill entrance.

Guest favorite

A two-story wooden lodge features a triangular gable roof and large front porch. The welcoming entrance is flanked by floor-to-ceiling windows, and vibrant flower beds are visible along the path. A well-maintained lawn offers a scenic backdrop under a partly cloudy sky.

Apartment in Orange

4.94 out of 5 average rating, 401 reviews

Cardinal Cove: Waterfront Kayaks Firepit Boatslip

Lakefront views. Three queen size beds, 2 deluxe air mattresses. 65" 4k SU Samsung tv (240 channels/11 movie channels; plus movies on-site). Quiet hours: 11pm-8am. Kayaks for 6 available upon request must return to storage rack face down or $25 cleaning fee.