Family-friendly holiday rentals in Culpeper

Downtown Suite with Outdoor Terrace

Transport yourself to your very own Italian Villa Terrace, located directly in the heart of Culpeper on Davis Street. Featuring a beautiful King bed, large soaking tub, ornate fireplace and stunning outdoor terrace for you to enjoy all to yourself, this space is one of a kind. Walk down the stairs and around the corner to all of the restaurants, shopping and breweries within a one minute walk. The suite has a shared entryway with one other suite (also available on Airbnb) but is very private.

3 Bed Tiny House in Culpeper w/ Kitchen & Firepit!

Welcome to our cozy tiny house in Culpeper, VA! This is the perfect retreat for couples/small groups looking for a unique & memorable experience. W/ open 2 lofts & a pull out couch this home sleeps up to 6 guests. The fully equipped kitchen allows for easy cooking. The composting toilet is an eco-friendly alternative w/o giving up convenience. Enjoy the outdoor fire pit & lounge area or visit some of the nearby attractions like Shenandoah National Park, shops downtown, & Death Ridge Brewery!

Aron’s Place (on the edge of Sugar Bottom)

Fully outfitted, completely separate apartment on the lower level of a private home in Culpeper VA with own entrance. Tempurpedic Queen Mattress. Bidet. Walk to historic downtown, restaurants, breweries, indoor climb, movie theater & retail. Close to wine trail, Commonwealth Park & Blue Ridge Mtns. Fenced yard with grill. LGBT Friendly. Well behaved pets, FLEA & TICK free, healthy, are welcome to stay but not be left alone for long. Property is 100% smoke/drug free. No parties. NO EXCEPTIONS.

Stylish & Cozy Getaway in Historic Culpeper

Welcome to your own private Culpeper retreat! This brand new house is the perfect place to unwind and soak in the experience of southern hospitality along with photo worthy moments. The outdoor space provides the perfect place to relax and take in the stunning sunset. You’ll love spending time outside, whether you’re grilling up a delicious meal or just lounging with a good book. Thoughtfully designed to provide a comfortable modern stay. Have fun with the whole family at this stylish place.

Bison Farm - Cabin "Brisa"

Bison Farm cabin in a very secluded section toward the back side of a 300 acre working bison farm. This is a tiny home Park Model with 400 sq. ft. and a nice spacious covered deck providing an outdoor living room. The kitchen has a 2-burner induction cook-top, a convection oven that is also a microwave and a small refrigerator and freezer two drawer unit that has decent space but is not a full sized appliance. Note: bison rotate pastures daily. Please don't expect them in your cabin view.

Red Fox Retreat

Easily walkable to Downtown Culpeper! This restored and newly renovated historic property allows easy access to Downtown Culpeper. It features a large outdoor fire pit and expansive grounds to spread out and relax. This 1000 sqft unit is located in the upper level with views of the surrounding grounds and trees. Brightly decorated and designed in partnership with Lets Go and Stay properties; the Red Fox retreat is a great place to stay while visiting Culpeper and the surrounding area.

Spacious Shenandoah Home on 35 Private Acres

Sitting on 35 acres of private land to be explored, this classic countryside vacation rental ticks all the boxes for a relaxing outdoors-geared getaway! You can practically picture yourself enjoying a glass of wine after a long day of exploring the natural beauty of Virginia from this perched hillside home, sporting a long private drive, and an expansive furnished deck. This 2-bed, 2.5-bath outdoors oasis is sure to have everyone unplugged, outside and enjoying living in the moment.

Comfortable and unique 1790's log cabin

Recently restored 1790's log cabin with modern amenities on a 30 acre 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.

Stanley’s Cabin- Beautiful farm with private pond

Located at the foothills of the Blue Ridge Mountains in rural Culpeper County, Stanley’s Cabin sits on a private 7 acre pond surrounded by trees, open land, and grazing cattle. Ideal for couples, families, or small groups! Play a game of corn hole, fish for large mouth bass, take the kayak or canoe on the water, or just enjoy a peaceful walk. Many tourist attractions and activities are within proximity. Stanley’s Cabin awaits your next adventure or trip for rest and relaxation!

Charming Restored Farmhouse Minutes from Culpeper

STRICT NO PETS POLICY! This spacious farmhouse, built in 1898, has been tastefully restored to accommodate modern living without sacrificing the charm of history. It is bright and airy, with open, spacious rooms and some smaller rooms for fun or quiet times. The house has a calming feel, with all the comforts of home. The farmhouse is a celebration of the richness of all things Virginia; its history, its vineyards, its fox hunts and the alluring charm of Old Virginia.

Mountain Cabin Getaway w/WiFi, TV, Fire Pit, Patio

This unique, modern A Frame cabin is located at the foothills of The Shenandoah Mountains only minutes from Old Rag Mountain, White Oak Canyon, trout fishing, horseback riding, wineries, breweries, and more! This 400 sq ft. tiny home has all the modern amenities you need to feel right at home. Step outside, enjoy the mountain air, and relax on your private patio with a cozy,private fire. Are your desired dates already booked? Check out our other listing, Black Bear Cabin!

Botanical Oasis in Downtown Culpeper

Botanical Oasis is a luxurious escape into a unique downtown property. Featuring calming neutral aesthetics, plant life, and two comfortable king beds; it's the perfect couples retreat or family getaway. This comfortable home sits in the center of downtown Culpeper in a hidden historic building just a few blocks from shops, dining, and drinks. Botanical Oasis is local to indoor rock climbing, vineyards, breweries, skyline drive, and hiking.