Vacation rentals with outdoor seating in Montgomery Village

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.

Cozy, Private Garden Apt in Derwood-La Belle Vie

Spacious one bedroom basement apartment. Private entrance, full bathroom and kitchenette all newly done. Freshly landscaped slate patio with garden and pond. The sound of running water provides a relaxing environment. Secluded back yard backs up to beautiful woods. 5 min away from bike trails. Large, open living space with sectional couch, and attached eating area with a table that can double as a work station. Centrally located in Montgomery County-approx 40 minutes from DC/Baltimore/Frederick.

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.

Private Garden Suite Near Metro to DC + Parking

Private, serene 1-bedroom garden suite with its own entrance, designed specifically for work-friendly longer stays and comfortable living near Washington, DC. Fully equipped with a dedicated workspace/chair, high-speed Wi-Fi, kitchenette and in-unit laundry for routine and convenience. Free parking included. Easy Metro access to DC, major hospitals, sports venues, and family neighborhoods—offering a comfortable, pet-friendly, well-located home base for work, rest, and visiting loved ones.

Cozy, clean 2 Bedrooms apartment!

The space is located on the lower level of a townhouse, with a private entrance from the street. 1 assigned parking & visitors spots. It is solely dedicated to hosting guests, small families on vacation, solo travelers for work, tourist. Another rental listing is located upstairs. Motion act camera outside the front door, please refrain of bringing more people than you booked. NO PARTIES ALLOWED, NO SOCIAL REUNIONS ALL GUEST MUST BE REGISTERED INTO THE AIRBNB SYSTEM BEFORE CHECKING IN

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 Crooked Cottage: a Cozy, Curated Escape

You will instantly relax in this stylish, pet-friendly home only 8 mins from I-70, exit 42. Under a canopy of trees find a beautifully landscaped yard with decks and two fire pit areas. Enjoy the well-apportioned kitchen with organic, fair trade coffee. Relax with 2 Roku TVs, games and puzzles, bathe with soaking salts and Turkish towels. For outdoor enthusiasts, pitch your tents. Sit by the wood-stove in the winter, or lay in a hammock when it’s warm. Welcome to The Crooked Cottage!

Urban Cottage, MD minutes from DC/National Harbor

Come and enjoy our spacious detached cottage,lounge on your private back deck overlooking private parkland forests. A real urban escape in an excellent location! Just a few blocks away from the MGM Resort / Casino, National Harbor, and shopping. Across the river from historic Alexandria and 10-minutes from Washington,DC. Great for a solo adventure,couples,and friends (up to 4 guests). Enjoy the seasonal steam house and personal wood-burning stove if you book in the cold months.

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.