Family-friendly holiday rentals in Orange County

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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 favourite

Home in Montpelier Station

4.93 out of 5 average rating, 508 reviews

The Cottage At Liberty Mill. Pets allowed $25

Brand new charming cabin with views of the Blue Ridge Mountains. Two bedrooms, Loft with 2 twin beds, two large bathrooms and a spacious common area. Exposed chestnut beams, working gas fireplace make this cabin a perfect getaway. All the amenities you could want. Located minutes from James Madisons' Montpelier, 5 minutes from Historic Orange, 30 minutes to Charlottesville, 20 minutes to Culpeper and less than 2 hours to Washington, DC. A loft area with 2 twin beds. Great for kids. Beautiful.

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Guest house in Orange

4.84 out of 5 average rating, 79 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

Chalet in Mineral

4.72 out of 5 average rating, 279 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 favourite

Flat in Somerset

4.98 out of 5 average rating, 176 reviews

Newly Renovated•Private Farm Apartment near Cville

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

Cottage in Madison

4.92 out of 5 average rating, 158 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.

Guest favourite

Cottage in Gordonsville

4.85 out of 5 average rating, 101 reviews

'Pond House' on Huge Horse/Cattle Farm

Our Pond House is on the shore of one of the most beautiful ponds you can imagine, in the center of our 600 acre farm. Great for young families. Fishing, swimming hole, trails, horses, cows, wildlife, rope swings, hot tub, Game Barn, peace & quiet. A number of state citation bass have been caught and released from the pond, and the cane-pole fishing is great as well. 35 min. to Monticello, 15 min. to Montpelier; 6 wineries; Great restaurants.

Superhost

Cottage in Gordonsville

4.88 out of 5 average rating, 8 reviews

A Charming Cottage on a Country Estate

Located on an 11-acre farm in the midst of Central Virginia’s wine country, the Cottage at Spotswood Lodge is a sanctuary for all who visit. The Cottage’s rustic charm speaks to its bygone days as the caretaker’s home for the original farmhouse, now known as Spotswood Lodge. Enjoy exclusive private access to this beautiful property by renting the Cottage (sleeps up to 7 guests and is equipped with a kitchenette - fridge/microwave only).

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 favourite

Home in Orange

4.97 out of 5 average rating, 119 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 favourite

Home in Aroda

4.89 out of 5 average rating, 113 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 suite in Madison

4.83 out of 5 average rating, 212 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 favourite

Flat in Orange

4.94 out of 5 average rating, 399 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.