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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.

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.

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.

Moon Hold Cottage - Retreat, Refresh, Recharge

Unplug from city life and venture out to our small organic farm. Spend a night or two in the private guest cottage while enjoying nearby vineyards and restaurants. Spend the day browsing in the local antique shops or relax on the farm and watch nature's display (butterflies, birds, an occasional critter.) We may be working in the garden or putting up hay. We're always glad to share a bit of the harvest when the vegetables are ripe, so you can take some home to enjoy. All are welcome here!

Adorable Cottage in Town&Parking

This sweet cottage is small, but cozy. It's within walking distance to Culpeper's many cute shops and delicious restaurants, and only a few blocks from the train for an easy weekend getaway. With the convenience does come a little noise with being in town - live music, traffic, the train, and maybe a friendly bark from my Goldendoodle Ruby. If you like to hike, there's many options for close by trails and of course within Shenandoah National Park. Come enjoy the cute town of Culpeper!

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.

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!

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!

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.

Sunny Cottage, POOL, Game Room, stocked pond

Full eat-in kitchen. Enjoy the local wineries and breweries! One bedroom cottage, queen bed, full kitchen on 12 acres 12 minutes from Warrenton! Adjacent to a 200+ acre state game preserve with walking trails. Enjoy our game room! This separate building hosts darts, an arcade machine (PAC-MAN, Galaga…) and a slate pool table. NOTE: Use the pool / fire pit, pond at your own risk! Pool is closed for the season.

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.

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.