Holiday houses in Middleburg

TDF Retreat on Kerr Lake

Come enjoy your own space at your own pace, directly on Kerr Lake. Quaint two bdrm/1 bath house on the Lake. 90 minutes from Raleigh or Richmond. This charming home, sleeps five, and is just steps to the dock which you can tie your boat up to. Longwood State Park is the closest boat ramp, and a mere 10 minute boat ride from there. Spend nights watching the sun set and sitting around the firepit making smores. Nonsmoking property. No vehicles on the back lawn. Please review cancellation policy

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.

Kerr Lake Amazing Views, Private Dock, Quiet

Peaceful lakefront retreat: Private dock, table, and new solar-lit umbrella (7/28/25). Amenities include a new gas grill (7/28/25), paddleboard, canoe, kayak, cornhole, hammock, firepit, puzzles, books, and games. Enjoy a large deck with two tables and a screened porch with couch—perfect for morning coffee. The home features 3 bedrooms, a loft, 3 full baths, and a dedicated workspace. Ideal for families, friends, or fishing trips. Driveway fits 5 trucks with trailers; boat launch 2 miles away.

Doc's Place - Newly Renovated - $0 Cleaning Fee

Forget your worries in this spacious and serene space where everyone is WELCOMED! Less than 4 minutes and you are in historic downtown Warrenton. Well kept and professionally cleaned. Newly renovated Doc's Place offers 4 bedrooms, 3 full bathrooms. Smart TV'S livingroom and loft. Brand new kitchen appliances. Comfortable patio with charcoal grill. Enjoy sitting on the front porch with the cool breeze from the fans and a nice cool drink. Private parking on premises. High speed internet.

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.

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.

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+).

Two Dachshund Farm (Lavender & Fiber Farm), LLC

Stay on a working fiber/lavender farm convenient to the Raleigh/Durham area - 20 min. from Interstate 85 & 50 min. from 95. Interact with our alpacas, sheep, llamas, Angora goats, donkeys, & more. Shop our farm store, stroll the property. Tours are free for registered guests. Friends may join the tour for a fee. Use of the pool is for registered guests only. Twenty stairs lead up to the 700 sq ft over-the-garage apartment with private entrance. Includes a king bed & pullout couch.

Charming Cabin at Seven Springs Farm and Vineyard

Kick back and relax in this calm, charming cabin on Seven Springs Farm and Vineyard. You'll experience tranquility the moment you step into the space with a breathtaking view overlooking the vines during the day and awe inspiring sunsets at night. Put your feet up and enjoy the scenery while lounging on the porch, or explore and walk with a glass of Seven Springs Farm and Vineyard wine. Either way, you're sure to have a memorable first-class adventure. Wifi available.

Quiet Kerr Lake Waterfront Home w/ Private Dock

Waterfront cottage on Kerr Lake (Buggs Island) in a quiet deep-water cove with private dock access via short golf cart ride. Screened back deck for morning coffee or evening cocktails with lake views. Garage hangout space, outdoor shower, and kayaks included. Four bedrooms split on either side of the living/kitchen area for privacy. Fast Wi-Fi and fully stocked kitchen for easy stays. Calm, swim-ready water and protected cove ideal for families, boating, and fishing.