Holiday rentals with outdoor seating in Culpeper

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!

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

Large Arcade ~ Hot tub ~ Firepit ~ BBQ ~ King Beds

Arcade game room! ~ Hot tub ~ Firepit ~ 48A Universal/Tesla EV Charger ~ Griddle BBQ ~ Large 4k TV in every bedroom ~ 3 King, 1 Queen, 2 full bunk beds ~ Board games ~ Outdoor games ~ Nearby wineries/breweries, Shenandoah National Park, Luray Caverns ~ High speed internet ~ Cell service ~ Dedicated workspace ~ Large dining room and fully stocked kitchen Welcome to Culpeper Manor! Our **newly refinished** spacious and luxurious vacation home, located on a wooded lot in a peaceful neighborhood.

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.

Taj Garage Guesthouse

Above garage guesthouse with private, self check-in entrance, off-street parking, among historic homes, 4 blocks to restaurants, shops, park, etc. in downtown Orange. Includes a fully equipped kitchen, queen bed, full bath, seating area, TV, wifi and balcony. Custom heart pine furniture, EV charger, refrig, stove, microwave, toaster and Keurig. Close to superb wineries, breweries and historic sites. Four blocks from the railroad so you will occasionally hear "that lonesome whistle blow".

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.

Private Fenced Yard for Dogs/Horses - 2BR Cottage

2BR Hen and Hound Cottage is located just outside Orange, VA and has a private fenced yard for pets and walk-in access to adjacent James Madison's Montpelier and its many walking trails. In addition, we are minutes away from all of the popular wedding venues in Orange and a short drive to Shenandoah National Park. Our house on Whistle Stop Farm (so named for the train that passes by) is next to the cottage if you need us. Otherwise, the place is yours. Come enjoy some time in country!

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.

Winters Retreat Farm Cottage - Entire house

Need a change of view? Unplug, and relax in this independent private cottage on the homestead. Watch for deer, turkeys and birds in the field from the sunroom or take a hike around the farm. Centered in Fauquier's wine country it is ideal for the weekend escape, or day trips West to the mountains, East to DC or points south. Also, a perfect solution for accommodating family at get-to-gathers, wedding guest, or your "Halfway overnight stay" traveler North/ South or to the beach.

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.

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.