Family-friendly holiday rentals in Lake Anna

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Lake Anna

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

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Superhost

Villa in Orange

5 out of 5 average rating, 53 reviews

Luxurious Stay for 2 at Historic Estate

Nestled on 13.6 acres of exquisitely landscaped gardens & grounds, Boxwood Villa (circa 1891) is a hidden gem for a couple’s retreat. Named for its stunning boxwood bushes encircling the property, this historic home was thoughtfully renovated by Leslie Gregg, the founder of The Market at Grelen. Her keen eye for contemporary comfort & preservation of historic design breathes new life into this historic manor. *Please note we only accept bookings for couples 30 days out from the requested dates.*

Guest favourite

Home in Orange

4.84 out of 5 average rating, 290 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

Superhost

Home in Bumpass

4.92 out of 5 average rating, 100 reviews

Lake Anna relaxation!

Lakefront on the private (warm) side of Lake Anna, guests are sure to enjoy a memorable vacation in this fully furnished, 4 bedroom/2.5 bath home. There is 1 king, 3 queen, bunks, and twin beds, comfortable for sleeping 11. The open living room has a 55" HD tv and a beautiful view of the lake. The kitchen is fully equipped for all your cooking needs. Situated lakefront, guests can enjoy sun and water fun, bonfires, and sunsets. A 7.3% transient occupancy tax will be included on all bookings

Superhost

Guest house 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

Chalet in Mineral

4.72 out of 5 average rating, 286 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!

Guest favourite

Home in Mineral

5 out of 5 average rating, 69 reviews

Honeysuckle Hideout: Waterfront Haven on Lake Anna

Less than 2 hours from D.C. but a world away, this newly renovated laid-back spot is great for groups, kids, and welcomes pets, too! Gorgeous lake views & sunsets from giant deck; a big lawn (good for Bocce, frisbee, soccer) slopes down to a secluded cove with recently expanded dock for sunbathing or floating the day away. Dogs are welcome! We also have a 1 BR guest house with kitchenette and bathroom that sleeps 4 that bigger groups can add for an extra fee. http://Airbnb.com/h/honeyguest1

Top guest favourite

Cabin in Spotsylvania Courthouse

4.97 out of 5 average rating, 434 reviews

The Tobacco Barn

A high-peaked ceiling and exposed-log crossbeams reveal the Tobacco Barn’s past life as a place for hanging tobacco leaves to dry. Now converted to a one-room guest house, it features a front porch swing, cozy fireplace, soapstone floors, a homey sitting area, and a tall, high-post bed. The pressed-tin ceiling and whiskey-barrel sink in the bathroom add to its charm. Pets are allowed and are charged a fee of $25 (first night) and $15 (per ea. add'l night). Maximum two-person occupancy.

Guest favourite

Cabin in Culpeper

4.97 out of 5 average rating, 189 reviews

Comfortable and unique 1790's log cabin

Recently restored 1790's log cabin with modern amenities on a 30 acre horse farm. Secluded wooded setting with pond view, less than 1,000 feet from main house and only 5 miles from downtown Culpeper with it's fine dining and quaint shops. Take a short drive to scenic Shenandoah hiking & biking trails, local vineyards and distilleries, Civil War sites, Commonwealth Equestrian Park, stroll around the farm or just unwind on the front porch or in front of the wood stove with a good book.

Superhost

Home in Culpeper

4.95 out of 5 average rating, 435 reviews

Cute Home in Downtown Culpeper with many extras!

Enjoy our recently updated home in downtown Culpeper. Our small home sits in a prime location within 1-3 blocks of amazing restaurants, breweries, and interesting shops.The house is located in a safe and quiet part of town. Convenient distance from Blue Ridge Mountain hiking. This property is professionally cleaned and sanitized after each reservation. Perfect for a family getaway! We are now accepting longer-term reservations. Top-rated accommodation in Culpeper for 2018-2022

Superhost

Home in Mineral

4.84 out of 5 average rating, 123 reviews

6BR 225' Lakefront Hot Tub Dock Private Boat Ramp

This spacious house has lots of decks and plenty of light, with beautiful mature trees providing plenty of shade and sun. The back yard leads to a nice 220-foot waterfront, private dock, and PRIVATE BOAT RAMP ON THE PROPERTY. A sandbox play area provides endless fun for children. A HOT TUB has been recently added that offers AMAZING views of the Lake. A stone fire pit next to the shoreline invites everyone to enjoy s'mores, campfire stories and unforgettable family memories

Superhost

Home in Spotsylvania Courthouse

4.85 out of 5 average rating, 187 reviews

Heavenly Quarters: Waterfront home for Family Fun!

A taste of Heaven awaits you. Our home has a private dock. We are located on a quiet cove off Pigeon Run near Lake Anna State Park and Lake Anna Winery. Only 2 hour drive to Washington DC. You’ll love my place because of the view, and you can relax in peace and quiet. Pet Free -No Animals of any kind permitted! Great for families. Check out our FB page to see more pictures - Heavenly Quarters - Lake Anna, VA When booking please list all guest with names.

Guest favourite

Home in Orange

4.98 out of 5 average rating, 124 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.