Holiday rentals in Midland

Winters Retreat Farm Cottage - Entire house

Need a change of view? Unplug, and relax in this independent private cottage on the homestead. Watch for deer, turkeys and birds in the field from the sunroom or take a hike around the farm. Centered in wine country, an ideal weekend escape, or day trips to the mountains, DC or points south. Also, a perfect solution for accommodating xtra family at get-to-gathers, wedding guest, or your "Halfway overnight stay" traveler North/ South or to the beach. Price increases due to new service fees.

Value · Family · Cleanliness

Lodge on the Lake

A quiet 17 acre, ONE room cabin set on a private small lake, fishing, swimming, and kayaking. Equipped with a full kitchen, a grill, 4 OUT DOOR showers, no showers in cabin. Sleeps 4, 1 QUEEN SIZE BED AND 1 PULL OUT HIDE-ABED. There is a $25/PP per day for extra guests , with prior approval by host. Pet friendly. Cameras are on site. 1 at the parking lot, 1 on the side deck, back deck, covered porch, up stairs open covered card/chest room, 2 on the main dock & water, 1 outside stone patio

Location · Value · Walkability

Garden Oasis outdoor entertainment at FrogPointe.

Nestled in between The Plains and Middleburg, this charming cottage is ready to help you relax. Perfect for family and friends during horse events nearby, like Gold Cup, Middleburg Film Festival, Christmas in Middleburg, Twighlight Polo, and much more. Fully functional kitchen with all you could need to cook a meal, fully furnished, indoor and outdoor dining, two large modern bathrooms, and internet / movies for a calm night in. Please be mindful this property is near a train track, charming!

Family · Location · Heating

Stylish & Cozy Getaway in Historic Culpeper

Welcome to your own private Culpeper retreat! This brand new house is the perfect place to unwind and soak in the experience of southern hospitality along with photo worthy moments. The outdoor space provides the perfect place to relax and take in the stunning sunset. You’ll love spending time outside, whether you’re grilling up a delicious meal or just lounging with a good book. Thoughtfully designed to provide a comfortable modern stay. Have fun with the whole family at this stylish place.

Value · Location · Walkability

Bison Farm - Cabin "Brisa"

Bison Farm cabin in a very secluded section toward the back side of a 300 acre working bison farm. This is a tiny home Park Model with 400 sq. ft. and a nice spacious covered deck providing an outdoor living room. The kitchen has a 2-burner induction cook-top, a convection oven that is also a microwave and a small refrigerator and freezer two drawer unit that has decent space but is not a full sized appliance. Note: bison rotate pastures daily. Please don't expect them in your cabin view.

Value · Location · EV charging

Luxury Private Basement w/ Theater+Arcade+Games

Unwind at this luxury private space that comes with this grand home. The space includes a state of the art theater room, Retro arcade machines, Billiard table, Dart board, Foosball, PlayStation video games and Ping pong table. Enjoy time with your family by hosting barbecues on the massive 10 acre lot along with a patio and deck that looks over the country side. The house is located in Nokesville, the area is often described as warm and friendly with local restaurants a 10 min drive away.

Value · Location · Cleanliness

Ruffner's Ridge

Relax with the whole family or bring a gathering to our peaceful place in Warrenton, VA. The home has just been renovated with high end finishes and maintains a cabin-type feel with vaulted ceilings and custom woodwork. Our beautiful home sits on 20 acres of open and wooded areas and has a small creek. There is ample room for parking and a large open field for activities. Near by you will find two fantastic wineries, a brewery, golf, and we are a short drive to downtown Warrenton, VA.

Value · Family · Hospitality

The Hayloft

🐞1 mile from the town of Middleburg, this one-of-a-kind bank barn has been newly renovated into a traveler's dream! Come with a group of your best friends to explore the local wineries or bring your family to enjoy the quaint town of Middleburg. 🎶 We host travelers and dreamers, not DJs and dance floors—no weddings or events, please. 🚭 Smoking is strictly prohibited anywhere on the property. 👙Get access to the Middleburg Community Center Pool for just $5 per person

Location · Family · Outdoor spaces

The Soper House-A Quaint & Lovely Country Getaway

The Soper House is a 1,000 sq.ft. ranch-style home with 3 bedrooms & 1 bath perfectly situated on a 5 acre farmette. Located in Fauquier County, VA. also known as Hunt, Horse & Wine country, each of the bedrooms uniquely displaying these historical themes. This charming cottage has a fully functional eat-in kitchen, a living room & a mudroom with W/D for your use. There are a few neighbors that are visible & we live in the adjacent property & can be easily available.

Value · Family · Access

Skyline Yurt: Hot Tub~Wood Stove~WiFi~Pet Friendly

Escape to Blue Ridge views at Skyline Yurt, a design-forward mountain retreat near Washington, DC. Watch the valley from the elevated deck, soak in the private year-round hot tub, and gather around the propane fire table as the sun sets. Inside, enjoy the soaring dome, wood stove, pool table, PS5 and fully stocked kitchen. Pet friendly and 20 minutes from Skyline Drive.

Location · Family · Access

Elda Gardens Cottage

Located on 30 acres 1 hour south of DC, surround yourself in nature at our farm cottage. Views of the vineyard and sheep will greet you at the front door. Quiet area in the heart of the Civil War history, let our cottage be your escape to the countryside. Enjoy all the seasonal delights the farm has to offer!

Family · Location · Indoor spaces

Lakeview Cabin

secluded nature paradise. Bird sanctuary. Bring your hiking boots, binoculars. This property is away from city lights, quiet, peaceful as the deer, wild turkey, native ducks and native birds of all kinds like it here. Cozy cabin in the middle of over 100 acres of pristine Virginia heritage land.

Value · Family · Wifi