Holiday rentals with outdoor seating in Montgomery Village

Spacious Private Lower Level Suite w/ Fast WiFi

✨ Private, bright lower-level suite (basement-level) with separate entrance in a single-family home near DC. Ideal for families or business trips 🛏️ Queen bed + large sofa bed (up to 3 guests) 🚿 Private full bathroom ☕ Coffee bar, dining area, smart TVs 📶 Fast Wi-Fi for work & streaming 🌿 Access to a nice backyard 🚗 Free driveway parking 🔑 Private entrance 🚶 ~20-min walk to Metro Quiet Rockville location near shops, dining & parks. Easy access to DC. Great value, comfort & convenience

Luna the Destination Camper

Just outside the buzz of D.C., Chesapeake Hideaway offers a peaceful, romantic retreat in the heart of Lanham. Surrounded by the natural beauty of Prince George’s County, this cozy RV features a queen+full bed, soft lighting, and panoramic windows for golden sunset views. Enjoy intimate meals in the charming kitchenette, then unwind on your private deck. Whether you're stargazing or exploring nearby Lake Artemisia and Greenbelt Park, this is the perfect spot to relax and make lasting memories.

‘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.

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.

Exclusive Home in Upscale Chevy Chase

You will love the secluded garden, near woods with deer and wildlife, the sunny kitchen with skylights, garden room, and large brick patio. Enjoy the 10-minute walk to Amazon Fresh, Starbucks and Einstein Bagels. One mile to Bethesda Metro; 1.5 miles to NIH, and Washington DC. Just1.8 miles to acclaimed restaurants in Bethesda and Kensington. 5G Wi-Fi, large workspaces. Centuries old trees. Self-check-in. Plentiful street parking. Only service dogs allowed / charged at $10 per day.

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!

Charming Cottage On Horse Farm Middleburg Area

The cottage is set on a beautiful private farm in the center of historic Aldie, Va. and 5 minutes to historic Middleburg. The cottage is surrounded by 11.11 privately fenced acres and is in a very cute setting with a shower and bathroom downstairs along with a kitchen and bedroom upstairs with one queen bed. The apartment accommodates 2 easily with table and chairs inside and on the porch for your comfort. Great opportunity to experience and relax on a small farm in hunt country.

Wooded Retreat in Great Falls

Escape to this wooded retreat in Great Falls, perfect for nature lovers and adventure seekers. This basement apartment boasts a dining area with sunlit windows showcasing vibrant forest views, a spacious living room, and a cozy bedroom. Enjoy easy access to hiking, biking, and outdoor fun in the parks just minutes away. Relax in the great outdoors experience the shops and dining in the nearby village. A perfect blend of nature and adventure awaits at this charming getaway.

Romantic Secluded Treehouse Stay in the Sky

Enjoy sounds of nature and view from our amazing treehouse nestled in the Poplar Trees surrounded by woods. Climb steep spiral staircase to a comfortable modern living area with kitchenette and another spiral staircase to a lovely bedroom with king size bed, bathroom and shower. Enjoy your morning coffee on side deck. During winter months you can see Sugarloaf Mountain in the distance. (Make sure to read the other details to note)booking a treehouse in a treehouse

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, and fully equipped kitchen. 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.

Historic Hillside Cottage

Experience the charm of an 1800s home styled with modern amenities. This historic cottage is steps away from all that Historic Ellicott City has to offer. Spend the day exploring Main Street lined with restaurants and small businesses or go for a walk, hike, bike ride or swim in nearby Patapsco State Park. Perfect for guests in town for weddings, concerts or those that love history and nature. Centrally located with easy access to Columbia, Baltimore & Washington D.C.