Family-friendly holiday rentals in Loudoun County

50-Acre Farmhouse Getaway Oasis in VA Wine Country

Just 1 hour from Washington DC, the spacious and tranquil Farmhouse at Dogwood Pond resides on 50 acres of land, and includes a large pond equipped for fishing. Our guests enjoy the nearby Purcellville Historic District for quality restaurants and cafes, vintage shopping, and the W&OD trail entrance at the old Purcellville train station. The property is also a swift 20 minute drive to historic downtown Leesburg, Waterford, Harper's Ferry, and endless wineries, breweries, hiking and bike trails.

The Hunt Box @ Tally Yo Farm

Residence above 5-stall horse barn. Two bedroom house with 2 bath, Juliette balcony, vaulted ceilings, fully appointed kitchen, laundry. Traditional English equestrian decor, with horse shows & fox hunts close by. Pool open 5/15-10/15. Extra guests $55/night. Pet fee $35 each. Please advise through Airbnb. Lovely antiques, equestrian art & decor, warm rugs. On site also~AirBnb: www.airbnb.com/rooms/826639006057875355?guests=1&adults=1&s=67&unique_share_id=4cdf4b76-3173-498a-9287-5ab54a38b4ee

Luxury Private Estate with 6 Bedrooms in Leesburg

luxury Private Estate in Leesburg. Perfect for family fun near wineries & breweries! with 6Bedrooms, huge owners suite & lux bath w/heated floors, soaking tub. The primary suite has a private living room that leads to a balcony. Huge open kitchen with high-end appliances, double wall-oven, oversized island, granite counters, skylights, heated floors, new sunroom, Bluetooth ceiling speakers. Covered Porch with Brand New Hot Tub. Beautiful outdoors with firepit under the stars. Welcome to Harmony.

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.

COZY3500sf Private-10acres Pool-PickleBall-Hot Tub

Immerse yourself in tranquility and laid-back luxury in our expansive home adorned with 6 cozy furnished bedrooms. Hemingway Retreat is nestled with 10 acres of spectacular farmland, with awe-inspiring vistas of horses grazing peacefully a picture-perfect escape from your routine life. With amenities such as fire pits, enjoyable hot tub, & tennis courts, indulge in a variety of recreational activities. Experience the fusion of comfort & exciting adventures at every corner of our property.

Private 24-Acre Countryside Retreat - No Fees!

Luxurious & cozy cottage, nestled in Virginia's wine country. With a gas fireplace, amazing beds & linens, gourmet kitchen with EVERYTHING and the great hospitality of owners Jennifer and Eric, you will have a premier visit! Self check in anytime and we are on the 26 acre property for 24/7 service. Beautiful vistas, wineries, and activities, over 250 five-star reviews (Airbnb& VRBO) max privacy and convenience. Relax in our tranquil setting while enjoying all the delights of the region!

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.

Whole House -Seven Elms Farm B&B

Come and enjoy peaceful setting of our 1870 farmhouse situated close to historical Town of Purcellville, great for shopping and enjoying a good meal, W&OD trail is nearby for a walk or a jog. Or you can just sit on either one of the two covered porches with a good book and take in natural open spaces and a view of a serene pond. And of course we are located in heart of Loudoun County's wine country, great spots for picnic and tasting of great selection of wines.

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.

Downtown Leesburg Cottage. Walk to everything!

Beautiful cottage in Downtown Leesburg! Walkable to all that Downtown has to offer! Across the street from the iconic Mom's Apple Pie and a short walk to restaurants, shopping, breweries and W&OD trail. Just a short drive to many local wineries, wedding venues, hiking and only 20 minutes from the Dulles Airport. Escape for the weekend or week and enjoy this beautiful 2 bedroom/1 bath home. Equipped with the essentials you need for a more than enjoyable stay!

The Studio

🐞1 mile from the center of Middleburg, this gem allows you to enjoy the beauty of a gorgeous Middleburg Farm when you stay in this unique tractor barn turned high end luxury studio apartment! This is for the customer who wants to experience country living but does not want to give up any luxury 🎶 We host travelers and dreamers, not DJs and dance floors—no weddings or events, please. 🚭 Smoking is strictly prohibited anywhere on the property.