Vacation rentals with outdoor seating 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.

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.

10-Acre Dog-Friendly House w Grill & Near Wineries

Welcome to the Reva Retreat! This country house sits on 10 acres, nestled between Shenandoah Nat'l Park & the Blue Ridge Mtns, with wineries and breweries nearby. Approx 1.5 hours from DC and 45 mins from Charlottesville makes this the perfect getaway destination to escape the city & unplug. Stocked with amenities: BBQ grill, dine al fresco, stargaze by the firepit, cook a feast in the new kitchen, play board games in the basement, or connect your laptop to a 32" monitor to work remotely.

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.

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

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.

CloudPointe Retreat

Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is recommended.

The Skyhouse- simple & serene w/mountain views

Enjoy the solace and beauty of the Blue Ridge Mountains with modern and local comforts. Retreat and explore on this old 100acre farm- via foot- or float on the tiny pond in a kayak or SUP. Or venture out to Shenandoah National Park, the local coffee shops, eateries, wineries, and breweries. Whatever you choose the skyhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

The Sparrow Luxury A-Frame w/Hot Tub in Shenandoah

Escape to The Sparrow, a newly built luxury A-Frame nestled in Virginia’s Shenandoah Valley, just a scenic drive from DC. This modern retreat features an African-inspired design, two bedrooms, a full kitchen, a fireplace, a private hot tub, a deck, a workspace, 4K TVs, and a PlayStation 5. Minutes from Luray Caverns, Skyline Drive, and Shenandoah National Park, it’s the perfect base for unforgettable adventure and relaxation.

Charming, Private 1 Bedroom Suite in Downtown

Come stay at the Whistle Stop Cottage in downtown Culpeper! Walk to this private guest house from the train station or pull right into the private driveway. The cottage is located along the train tracks and is a detached part of a larger residence. The suite is one bedroom with a king sized bed, and one full (newly renovated) bathroom. Walking distance to shops and restaurants and overlooks beautiful gardens.