Guesthouse vacation rentals in Fauquier County

Three Meadows Farm, outdoor views, great location

As you approach the driveway on the private lane, you'll be welcomed by beautiful meadows and rolling hills. Set on 10 acres in a shaded, forest of mature trees it's comfortable year round. There are beautiful mountain views from several locations on the property. It's peaceful and quiet here most of the time. We're conveniently located just minutes from Flint Hill, not much farther to Washington VA, Sperryville and Front Royal. It's a two bedroom/one bathroom apartment above a detached garage.

Family · Location · Laundry

18th Century Middleburg Cottage

This recently renovated 2-story 18th Century stone cottage is the perfect blend of rustic and luxury, featuring stone walls, exposed beams, wood floors, a stone patio and outdoor fireplace, as well as Mountain views. Property includes kitchen, bathroom, and a living space with wood stove and dining table. Upper floor features bedroom and additional reading room. Cottage is just minutes from historic Middleburg in the heart of horse and wine country, perfect for relaxing or recharging getaways.

Value · Location · Long stay

Romantic Carriage House - 1 Bedroom Loft Apt

Welcome to Gracecliffe Loft - A very private, exceptionally clean and bright, detached carriage house loft apartment in the heart of Virginia horse and wine country. You will find peace and beauty everywhere you look. Set upon 10 acres of rolling hills, woods, a beautiful stream, and a private fire pit for chilly nights and a swimming pool during the warm months. Only 4 miles from downtown Middleburg, 5 miles from Salamander Resort surrounded by many wineries and horses everywhere you turn.

Location · Family · Backyard

Tranquil Country Gem

This is a light-filled, very private and extremely tranquil guest cottage set on an estate property in Middleburg. Enjoy gorgeous paddock and river views from the wrap-around decks. Spend time watching the plentiful deer, fox, turkey, hawks, woodpeckers, and more from the decks or sunroom. Owners are on property, but you are separated by a thick parcel of woods. Three miles to the charming village of Middleburg and one mile to multiple wineries. This is a working farm with cattle and horses.

Family · Location · Check-in

The Winehouse at Mount Airy

Welcome to The Winehouse, our charming, and rustic cottage on the grounds of Mount Airy, a historic Civil War era home in Culpeper County, Virginia. Steeped in history and surrounded by tranquility, this idyllic retreat offers modern comfort and convenient access to wineries, downtown shops and restaurants, and the beautiful Shenandoah National Park. The location is also ideal for cycling enthusiasts who want to enjoy riding on less traveled country roads that offer spectacular scenery.

Family · Location · Sleep quality

Fox Hill Barn Guest Cottage Retreat

Enjoy the lovely setting of this romantic spot in nature, just minutes from the historic charm of Middleburg. Set on a tranquil horse property, this cottage offers a serene retreat amidst rolling pastures and breathtaking views. Whether you're a nature enthusiast, equestrian, remote worker, or seeking a romantic getaway, this is your ideal destination. Enjoy nearby wineries, breweries, scenic trails, and the delightful town of Middleburg—only 3 minutes away. Life is too short. Enjoy!

Value · Location · Access

Watson Hidden Gem Guesthouse Apartment

This newly built apartment features a bright, open-concept layout with polished concrete floors, clean lines, and thoughtfully curated furnishings. The living area is designed for relaxation, with a comfortable sofa, cozy seating, and a large TV. The fully equipped kitchen includes everything you need. What truly sets this space apart is its setting — surrounded by open land and natural beauty, you’ll enjoy a level of privacy and tranquility that’s hard to find.

Rare Mountain Views in Culpeper ~ Hot tub ~ Arcade

Mountain Views ~ Hot tub ~ Large 4k TVs ~ 1 King, 1 bunk bed ~ Board games ~ Fully stocked kitchen ~ Nearby wineries/breweries, Minutes from downtown Culpeper ~ Shenandoah National Park, Luray Caverns ~ High speed internet ~ Cell service Welcome to Culpeper Meadows! Our newly refinished home with breathtaking mountain views. Nestled on a old farm field in a peaceful neighborhood of 10 acre lots, it's the perfect retreat for relaxation and adventure!

Value · Family · Hospitality

Peace of the Country! Guesthouse in Fredericksburg

Forget your worries in this spacious and serene space. Country living! Private Entry, Ample Parking Spaces, Full Kitchen, Private Full Bathroom with full-size washer and dryer. 55inch TV in sitting area with cable. 55 inch TV in bedroom with Roku Stick. Wifi if your working remotely. Smoke Free and Clean Home. 1 bedroom, Queen Size Bed. Security System and wonderful host! *this is a separate space in our home* we work remote and are home also *

Summer kitchen guesthouse at Caledonia Farm 1812

Summer kitchen guesthouse built of stone in 1812 and located on a 115 acre free-range cattle farm on the National Register of Historic Places. The first floor is a living room with the original cooking fireplace and a kitchenette. Upstairs is a loft bedroom and bath. Housekeeping is provided on Monday and Friday mornings. Enjoy the peace and quiet, dark skies, scenic views, adventure, and culinary excellence of Rappahannock County.

Value · Location · Backyard

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.

Family · Location · Getting around

A lovely cottage in The Plains, Virginia

The Cottage in The Plains recently underwent a full renovation. It is short walk to restaurants and shops in The Plains and a short driving distance to many attractions (e.g., vineyards, Middleburg, Upperville, and Gold Cup). This one bedroom, 1 bath cottage with full kitchen, living & dining area, work space, and washer and dryer has everything you need for a fabulous weekend getaway or extended stay.

Location · Family · Outdoor spaces