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*Cottage @ Firefly Cellars* VA Wine Country escape

The Cottage at Firefly Cellars is a private, tranquil escape on the tasting room property. Come enjoy the private pool (in summer months), walk the property with a glass of wine, enjoy views of the neighboring horses, hop to local wineries, or just sit back and enjoy all the cottage has to offer. The cottage is meticulously maintained, beautifully designed, and you will feel at home the moment you walk through the doors. Perfect for a couple, or an individual looking to escape from busy life!

Walk to Downtown, Relax by Fire

Escape to our beautifully updated 3-bed, 3-bath home in Historic Downtown Leesburg, perfect for 5 guests. Enjoy a private backyard with a smokeless fire pit, a fully equipped kitchen, and a dedicated workspace. Just a short walk to downtown's best restaurants, shops, and breweries. Ideal for wedding weekends, family trips, and getaways. One of several homes in the Historic Leesburg Stays collection — locally hosted, thoughtfully restored rentals across historic Leesburg and Loudoun wine country.

Oatlands Creek cabin

Welcome to Oatlands Creek, the ideal getaway for relaxing and exploring Old Town Leesburg, Aldie, and Middleburg. Set on 22 private acres, driving up you’ll be greeted by horses in the neighborhood. This beautifully renovated cabin blends rustic charm with modern comforts, featuring 4 spacious bedrooms, an open dining and living space, theater room, game room, and hot tub. Whether you’re here for wine country, family visits, bachelorette parties, or work, this cabin is the perfect spot for you.

Hummingbirds Hideaway Treehouse

Do not book on airbnb and ask for early arrival. experience the magic of being among the treetops at our newly built treehouse. Whether you are seeking a romantic getaway, peaceful retreat, or family fun this slice of heaven will offer you an unforgettable stay. Features large windows for stunning views of the surrounding woods and very detailed woodwork. 2 bedrooms with king beds, open living space with full kitchen and bathroom will be sure to impress. Please message us prior to booking

‘Waterfront’ Farm Escape for Hikers & Wine Lovers

Feel refreshed when you stay in this rustic gem! The Springhouse is nestled in the rolling hills of Northern Virginia’s Wine Country! Originally constructed in the early 1800's, the structure was built over a natural spring that was used for refrigeration. Water from the spring maintains a constant cool temperature throughout the year while also filling a pond. The original stone well, channel and stone flooring are all intact for guests to explore and experience how our ancestors lived.

The Villa on Lakeside

The Villa is a stunning single-level residence with a half-acre fenced yard. Your entire family, including your beloved furr babies, is warmly welcomed here. The villa features 3 bedrooms and two newly renovated bathrooms, each boasting heated bidet toilet seats. For remote workers, the office is equipped with a wireless printer and a phone. The kitchen is designed with high-end appliances, including a built-in coffee maker. Additionally, a full laundry room is available for your convenience.

Hope Flower Farm Winery Cottage

Welcome to Hope Flower Farm & Winery! This charming 3-bedroom, 1-bath cottage is the perfect retreat for those seeking a peaceful getaway in the heart of Loudoun County wine country. The cottage features a kitchen, cozy living room, and a screened-in porch perfect for enjoying your morning coffee or an evening glass of wine. The cowboy cauldron is the perfect spot for roasting marshmallows or enjoying a cozy fire. Come experience the beauty and tranquility of Hope Flower Farm & Winery.

The Forge on Sunnyside Farm

Sunnyside Farm offers a luxurious stay in a beautifully restored historic forge. You’ll be greeted by the farm’s delightful hosts, Jimmy and Dean, two friendly Potbelly pigs. Beautiful cows forage right outside your door. The Forge features exposed wooden beams, brick walls, and cozy furnishings. The interior is designed with plush bedding, a fully equipped kitchen, and spacious living reminiscent of yesteryear. Breweries, wineries and famous antique stores nearby offer entertainment.

The Weaver’s Cottage c. 1815

Welcome to The Weaver’s Cottage c. 1815! This unique and peaceful historic property has been lovingly restored to maintain its original period character while providing modern convenience. Located in historic Waterford, VA, a National Historic Landmark, and close to many farmer’s markets, wineries, breweries, distilleries, restaurants, antiquing, endless outdoor activities, and more, you won’t lack for fun local things to do! The history of the village itself deserves to be explored.

The Cottage at Forest Hills Farm

Beautiful one bedroom, one bath cottage on a picturesque 14 acre farm just outside of downtown Leesburg. Nestled in close to local vineyards, this charming, free-standing cottage is yours and perfect for a weekend getaway or alternative to a hotel. Enjoy the fresh air, beautiful views, and peace and quiet on our little farm. Wander the property and say hello to our donkey, mule, Long Horn cows, goats, chickens, and 3 barn cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

Restored 1820 Waterford Village Farmhouse

We restored this 1820 village farmhouse in 2016. It is situated in the heart of the historic village of Waterford. It has 2 1/2 acres behind, with two barns, a herd of very friendly goats, chickens, and vegetable, herb and flower gardens. The house backs up to The Phillips Farm, 150 acres of preserved land and public walking trails. Beautiful sunset views from the back porch. The house, a work in progress, was featured in both Country Living and Preservation Magazines.

Trailside Chalet (A storybook chalet with hot tub)

The Trailside Chalet is situated on the W and OD Trail, halfway between Leesburg and Purcellville, Va - an ideal base location for visiting wineries, breweries, and the pastoral countryside of Loudoun County. The chalet will put you just steps from the trail for walking/cycling/horseback riding. Relax and enjoy the amenities of one-of-a-kind interior including wood burning fireplace and peaceful surroundings with hot tub. A perfect getaway for a couple or family.