Family-friendly holiday rentals in Augusta County

"Country Star"- Suite at Cross Keys

Welcome to our private, cozy suite, Country Star. A sunny walkout basement apartment with patio and easy parking next to entrance makes coming and going a breeze. Country Star features a kitchenette, with table and chairs, one bedroom with queen bed and closet, and a full bath/shower. It provides comfortable space for two, with extra space for a pack-n-play or fold out lounge chair/bed for a third person. (See note in 'other'). Our space offers convenience and comfort, with self check-in.

The LoriAnn, A Boutique Stay New Sleep Number Bed

This beautifully restored 1940’s home in the City of Waynesboro is just a short drive from the Blue Ridge Parkway. Modern amenities, light complimentary breakfast items and assurance of comfort awaits! Enjoy one of a kind Autographed Movie and TV Memorabilia. The spacious front porch is yours to enjoy including a 100 yr old porch swing that belonged to my Great Grandmother. Along with the Parkway & Skyline Drive, enjoy Restaurants, Breweries, Vineyards, movie theaters and exploring Route 151.

Bee & Key—Staunton downtown

Staunton (pronounced “Stanton”) is one of the most vibrant, charming small towns you’ll find anywhere, and Bee & Key is in the center of it. This bright and stylish apartment is on the second floor of a grand 1885 home on East Beverley St. You will be half a block from the restaurants and shops of our bustling downtown, including Blackfriar’s Playhouse, the Woodrow Wilson Museum, The Shack restaurant, and Mary Baldwin University. We’re an easy walk from Staunton’s historic Amtrak station.

The Firefly Cottage

This century old cottage, updated with modern comforts, is perfect for a long or short stay and is located on our family farm. Minutes from downtown Staunton or Interstates 81/64. Relax, stretch out in four rooms, get some laundry done. Enjoy the peace of the rural setting. Queen size bed, large shower, fully equipped kitchen with dishes, cooking utensils, range/stove, microwave, refrigerator, and dishwasher. Washer and dryer. Private parking. All varieties of people are welcome here.

1 bedroom condo, walk to the slopes !

Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and close access to the village for après-ski.

Mountain Views, Hot Tub, Treehouse & Game Room

Escape to Serenity Ridge, your secluded Shenandoah Valley oasis in the country. With ample outdoor spaces for relaxation, reflection, and unwinding. Surrounded by mountain veiws and abundant wildlife, enjoy hot tub relaxation," "treehouse adventures," and "game room fun. Whether you're a couple seeking a private getaway or multiple families looking for a perfect meeting place, Serenity Ridge has everything you need. Top Attractions: Shenandoah National Park Staunton JMU Buc-ee's

The Laurel Hill Treehouse

Tucked away in the woods, this Scandinavian-inspired treehouse is a quiet, peaceful spot designed for a relaxed couples getaway. Surrounded by trees and overlooking beautiful woodland views, it’s an easy place to slow down and unwind. Spend your time on the wraparound porch, soak in the hot tub, cool off in the creek, or settle in by the fire at night. This is a serene, comfortable retreat where you can reset, enjoy all that nature has to offer, and simply be present.

Little Cabin in the Woods is quiet and secluded!

Enjoy our rustic, cozy, historic log cabin in the woods on 21 acres with two streams and a little meadow. The logs, from the 1800's, were reconfigured 17 years ago combining a rich history with high speed internet and modern amenities. Sink into the luscious bed with totally organic sheets, mattress topper, and pillows. Take a walk on the original wagon train road down to a stream or bath your senses in the majestic view of Jump Mountain from the meadow.

Mountaintop Overlook – Updated 2BR w/ Deck & Views

Breathe in the crisp mountain air, cozy up by the fireplace, and soak in sweeping views of the Blue Ridge Mountains. This clean, comfortable 2-bedroom condo at Wintergreen Resort features two king beds, two full bathrooms, and a sleeper sofa—perfect for up to 6 guests. Enjoy panoramic windows overlooking the mountains,, a fully stocked kitchen, in-unit washer/dryer, central heat/AC, and free parking. The shuttle to the ski lodge is just steps away!

Travelers Nook - close to downtown

The TRAVELERS NOOK is a cute, cozy, one bedroom apartment close to downtown Staunton! It’s located on the second floor, with a private entrance. It has all the charm that you would expect to find in a cute studio apartment! Built by a local architect Tj Collins in the 1920’s. This quaint space has everything you need to enjoy your stay here in Staunton! We do accept small pets on approval with a pet cleaning charge.

Wintergreen Escape | King Bed + Porch Views

Escape to our four-season Wintergreen condo! Enjoy crisp mountain air, scenic hikes, fall foliage, and nearby wineries and breweries. Walk to Discovery Ridge, the spa, and activities! Relax at the seasonal heated pool, play a round of golf, or explore the Blue Ridge Parkway and Shenandoah National Park. Perfect for couples or families, cook a cozy meal or unwind by the fire after a day outdoors!

Walker's dream. Close to downtown.

Centrally located near the library, Gypsy Hill Park, and downtown Staunton, our private, walkout basement apartment has individually controlled heating and air conditioning. It includes a brick patio, private rear entrance and historic details from the late 1800's. It is generally quiet, but you may sometimes hear the two adults upstairs. Come enjoy this peaceful and centrally-located space.