Family-friendly holiday rentals in Leesburg

Private 2 BR, 1 Bath Carriage House Near Wineries!

Fox Farm Carriage Apartment is a private country retreat, located on 10 acres, on a quiet, private road. It has 2 bedrooms, one bath, with incredible views (the sunsets are amazing) and filled with natural light. It has a private entrance w/ staircase to 2nd floor. The bath has a luxury shower and dual vanities. It has a full kitchen stocked with cookware, Direct TV, and large family room. Very close to Leesburg and local wineries and breweries. Linens and towels, soaps, shampoos are included.

The Crown Cottage @ Historic Leesburg

Come stay at your home away from home. You will be in the heart of Historic Leesburg within walking distance to everything Leesburg has to offer. Fios Internet - Gigabit Speeds 2 - 65" Flat Screens - free Hulu (live), Netflix & Amazon Fire pit with Firewood (6 Adirondack chairs) Barbecue for Fire pit Fenced Backyard w/Patio and Dining Area Nespresso coffee machine (coffee included decaf/regular), kettle & tea selections) Phone charging stations in every room Washer & Dryer Parking in Driveway

Leesburg Hideaway w/ King Bed + Private Backyard

Escape to this light-filled two bedroom, one bathroom bungalow located minutes from the heart of Leesburg's historic district. Just a short drive from unique shops, restaurants, and outdoor activities. This is the perfect home base whether you're in town for a weekend getaway or an extended stay. Located near the W&OD Bike Trail, Birkby House, Morven Park, breweries, wineries,and Rust Manor. We're excited to host you in our little slice of Leesburg charm! Bikes included: 1 mtn. & 1 cruiser

Romantic Barn Loft near Downtown Leesburg!

How about a Summer Escape to the Country? Welcome to Windy Hill Loft! This is a completely unique stay experience in the Loft built inside our Big Red Barn! Imagine relaxing in this charming space all while overlooking our horses, our adorable mini cows AND the mountains in the heart of Virginia Wine Country. Within 2 miles of some of the best wineries in the area and only a 15 min. drive into downtown Leesburg, Windy Hill is the perfect place to relax after a fun day in the Country!

The Loft at Lakeside

Welcome to the The loft at Lakeside! The loft is a completely separate space that comes with its own entrance and parking space. The loft consists of a spacious bedroom with a walk-in closet. There is a full bathroom in the bedroom and a half bath near the kitchen. The main space consists of spacious Kitchen that sits right next to the cozy family room, with a large couch. It also has a full laundry room for anyone looking to take home clean clothes after an amazing stay at The Loft.

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.

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!

Historic Farmhouse in Beautiful Western Loudoun

Historic beautifully restored stone house located on beautiful farm property just outside of Leesburg VA. The house is a perfect spot to unwind, relax, and come explore Loudoun County which is filled with wineries, breweries, farm to table restaurants, hiking trails and more! Beautifully decorated space, king size bed, large comfy couch, dining room and kitchen are a few highlights of the space. This is the entire house. Looking forward to your stay!

Suite GG ~ Relax & Enjoy

Let this cozy above-garage apartment be your home away from home. Located in Lucketts, VA we are within a short distance to the small artsy town of Leesburg, local wineries, breweries, antique stores, shopping outlets, hiking, biking and canoeing/kayaking on the Potomac River. Our spacious, fully-furnished apartment with private entrance sits above a detached garage and features a lovely raised deck overlooking the back gardens.