Holiday rentals in Middleburg

A-FRAME Lake Cabin. Private Boat Dock, Kayaks, SUP

BRAND NEW (2022) custom lakefront A-Frame Cabin. Mid-Century Modern. You'll love the stylish cottage & all the outdoor living/playing. Close walk to your own private dock (2 boat slips) and boat ramps close by. Located right on Kerr Lake (aka Buggs Island). NEW for 2024; ALL NEW BATHROOM, NEW stable internet, concrete sidewalk, Solostove firepit patio, NEW hot tub, patio lights, gas grill, outdoor shower. Toys left out; wagon for hauling, kids kayak, adult kayak, paddle board, and beach chairs.

No cleaning fee! Flexible check-in & out times!

Slow down at our cozy 3 BR-2 Bath lake home, tucked back in the woods with a quiet view of the cove. Lots of deck space to relax and enjoy nature. If you are feeling more adventurous; Paddle on the lake, play cornhole, or hike on our private trails. And speaking of hiking, we said “take a hike” to cleaning fees (who likes those?), And check-in/checkout times; ours are so flexible they practically do yoga. Stress-free? Absolutely. Deer-approved? 100% They may even pose for a picture with you.

Mary's Place ❤ Bright 3BR with deck/private yard

Mary's Place, a charming cottage renovated in 2022, is nestled in the historic walkable town of Warrenton. With all the comforts of home, this peaceful haven is ideal for any traveler-couples, families, or singles. Complete with extras, like a coffee station, a king sized bed and cozy fireplace in the master suite, and a deck that wraps around to the spacious backyard. The oak tree shaded back deck is perfect for taking in that sweet southern breeze with a cup of coffee or a glass of wine.

The Seed House: Octagonal Barn, Dog-Friendly!

Two blocks from the ❤︎ of charming Main St. Warrenton sits an unusually shaped barn. Octagonal living at its finest; The Seed House is fully renovated and features modern amenities like wifi, coffee, tea, kitchen basics, 100% cotton linens, smart TV, games, and yoga gear. The barn is nestled at the tree line, bordered by a huge lawn + gardens. Your stay will be relaxing and private and leave you with a special sense of place. *Dog-friendly with prior approval. See House Rules for more info.

Historic Warrenton Small Cabin

Beautiful guest house, located steps from the main house, hidden from public. The cabin is tucked away in our manicure backyard. Spacious fenced in yard where your fur babies can run free. Enjoy the large pergola with comfy seating for nighttime relaxation or dining. The house offers a living room, kitchenette (NO STOVE) and spacious bathroom. The second floor is a large LOFT with a dividing wall separating the two sleeping areas. There are 13 steps to the second floor. ABSOLUTELY NO PARTY!

Modern Woodland Retreat

Welcome to Fox Hollow, a stylish and comfortable retreat on two peaceful acres. Convenient to both Raleigh and Durham, but tucked away in a quiet wooded neighborhood, you'll experience the best of both worlds. Guests of all ages will enjoy the rec space with ping pong, foosball, and more. Whether you're planning a long vacation or short getaway, the private spa and built-in fire pit will make your stay memorable and the fully stocked kitchen and comfortable beds will make you feel at home.

Lakefront Cottage w/ great view and use of dock

The sunlit cottage is perfect place to enjoy the largest lake in Virginia, exploring nearby state parks, the quaint town of Clarksville, or nearby breweries/wineries. The cottage offers an open view of the lake and use of a dock (150 yds from house) for fishing, swiming, docking watercraft or watching the sunset. A great retreat for a small family of 4 or 2 couples. Please indicate the number of guests; parties over 4 must be pre-approved. Reservation must be by an adult (age 21+).

Satterwhite Retreat

Located within a short 10 minute drive of Kerr Lake; Satterwhite Retreat offers boaters, fisherman, motocross bikers and the entire family a relaxing getaway. Conveniently located off I-85, Satterwhite Retreat is in the heart of lake country & a short drive to Clarksville, VA, Warrenton, Oxford & Henderson, NC. Boat and RV parking available. A boat charging outlet is conveniently located adjacent to the parking area. TV's in living room and one guest bedroom. Well-lit for night arrivals.

Woodleaf Wayside

An 1850s cottage listed on the National Register of Historic Places was the Plantation Office for the Massenburg Plantation (Woodleaf). It was restored in 1990 and afterwards, became rental property. This two-story, cozy hideaway has a private drive and patio. Native stone and hand hewn beams in basement bedroom provide an unique stay. Full kitchen, modern bathroom, and washer/dryer. Come and go at your leisure. You will receive a keypad combination a day before your scheduled check-in.

New Lake House Sanctuary: Modern Elegance #2

Escape to our luxurious lakeside retreat, where tranquility meets modern comfort. This stunning home is perfect for families, groups of friends, or corporate retreats. Our home features stylish, contemporary decor that blends comfort with sophistication. The spacious open-plan living area includes plush seating and a state-of-the-art kitchen fully equipped for all your culinary needs that includes modern appliances, cookware, and dinnerware for your convenience.

Bracey Historic Train Depot

Want to step back in time to the late 1800's? Staying at the historic Bracey Train Depot will give you that experience and more. The Depot is among one of the surviving buildings with the old post office across the street, the general store next door and landmarks. This section of Bracey Drive is at times secluded, just around the 'cut' and a half mile from I-85.

The Browns house with autumn colors

This is a two bedroom two bathroom house, but only one bedroom is being offered. If you rent you get the entire house to yourself. The other bedroom will be locked at all times. It is a huge house with plenty of space and fully stocked kitchen with dishes, cookware appliancesvery nice dining room queen size bed being offered with walk-in shower in the bathroom.