Vacation rentals in Middleburg

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Top-rated vacation rentals in Middleburg

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Guest favorite
The game room features a blue felt pool table at its center, surrounded by wooden shuffleboard and dartboard areas. Two tall bistro-style tables with chairs are positioned against the walls. Natural light enters through multiple windows, while decorative elements provide a rustic touch.
Home in Franklinton
4.94 out of 5 average rating, 129 reviews

Nature Lover's Getaway!

Want to get away from the hustle and bustle of life? This is the place for you! Kick back and relax in this stylish home, far enough out of the city to get away, but close enough to enjoy the benefits of city life. Be aware - the house sits on a .5 mile bumpy dirt road, worth it if you are looking for peace and quiet. Due to the location, the best we can do is a data-limited hotspot for WIFI. So, we added a game room. Pets are welcome. The cost is $30 a night per pet that is paid separately.

Top guest favorite
A wooden dock extends over the calm water, featuring two light-colored chairs and a shaded umbrella. Surrounding trees and distant structures create a natural border along the lake, highlighted by a clear sky with gentle clouds.
Cottage in Henderson
4.96 out of 5 average rating, 54 reviews

Kerr Lake sunsets at Cypress Cove Cottage

Built in 1958, updated in 2019, Cypress Cove Cottage on Kerr Lake is a place to relax, have a refreshing swim, and view stunning sunsets. Originally a summer home, called Sunnyside, the cottage was winterized for a year-round retreat. Bald cypress trees bookend the lakeshore of this unique property. The cottage is on a grassy lot sloping gently to the lake. There is a small dock to fish, swim and watch sunsets. Great spot for lake lifers, fisherfolk, couples, small families, business travelers.

Guest favorite
Cottage in Warren County
4.86 out of 5 average rating, 166 reviews

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.

Top guest favorite
A wooden dock extends into calm waters, reflecting the soft colors of dusk. Lush greenery surrounds the lake, with trees visible along the shoreline. A gentle rise in the landscape creates a serene backdrop, while the moonlight begins to peek through the evening sky.
Home in Clarksville
4.93 out of 5 average rating, 136 reviews

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.

Top guest favorite
Barn in Warrenton
4.97 out of 5 average rating, 196 reviews

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.

Top guest favorite
Cottage in Warrenton
5 out of 5 average rating, 108 reviews

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.

Top guest favorite
The outdoor swimming pool features a curved design with blue tiles along the edges. A lounge chair and two umbrellas provide shaded seating. Colorful pool floats are positioned nearby, and a spacious grassy area surrounds the pool, enhancing the outdoor setting.
Cabin in Warrenton
5 out of 5 average rating, 165 reviews

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!

Guest favorite
Home in Henderson
5 out of 5 average rating, 16 reviews

Lovely Stay By Kerr Lake

Welcome to your home away from home! This spacious 3-bedroom, 2-bathroom house is perfect for families and groups looking for comfort and convenience. With plenty of room for everyone to relax, the home features a fully equipped kitchen, cozy living areas, and all the essentials you need for a stress-free stay. Whether you’re gathering for a family getaway, celebrating a special occasion, or just enjoying time together, this home offers the space and amenities to make your trip memorable.

Top guest favorite
Farm stay in Franklinton
5 out of 5 average rating, 169 reviews

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.

Top guest favorite
A welcoming cabin entrance features a spacious porch with multiple steps leading up. The rustic wooden exterior is complemented by large windows. Lush greenery and colorful plants surround a stone pathway, enhancing the natural setting among the surrounding trees.
Cabin in Youngsville
4.97 out of 5 average rating, 115 reviews

Cabin Retreat Near Town

Relax with the whole family in this warm and spacious cabin nestled on 11 wooded acres. A long gravel driveway leads you beside two beautiful horse farms with your private retreat tucked away in the woods. You will enjoy all of the benefits of a private, wooded retreat while conveniently located just minutes from all that Wake Forest, Youngsville, and Franklinton have to offer. Screened porches, a spacious open concept living room/kitchen area, with two adorable bedrooms.

Guest favorite
A wooden dock extends over the shimmering surface of Lake Gaston, framed by lush trees along the shoreline. A lounge chair and a small round table provide a space for relaxation, while a decorative statue resides nearby, adding character to the inviting setting.
Home in Boydton
4.9 out of 5 average rating, 146 reviews

Lovely Lake Gaston

Lovely 3 bedroom, 3 bath home on Lake Gaston. The waterfront property also has a boat dock and place to dock and tie up your own boat. There is a neighborhood boat ramp.. There are 2 single kayaks, and firepit.. The gourmet kitchen is well equipped with whatever you need. In season, there is an herb garden for guest use. The home is set in a quiet neighborhood that allows privacy. There is extra sleeping space with a queen size air mattress and 2 sofas (not sofa beds)..

Guest favorite
Home in Warrenton
4.95 out of 5 average rating, 304 reviews

The Peete House and Garden- Entire House

Welcome to the Peete House, a 1911, 4700 sq. ft. neoclassical home in downtown Warrenton. Two blocks from restaurants, bars, the library, antique stores and more. Architectural and gardening interests flourish here. Come explore the large koi pond, two acre garden, and the additional two antebellum houses that reside on property. This home is unique in that it can host a family with 5 bedrooms; 3 are King Suites. Small parties are possible for an additional fee.

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