Holiday houses in Wylliesburg

5.0 out of 5 average rating, 10 reviews

Dockside Dreamz #1 w/beach & dock

The downstairs unit of this lakefront duplex offers stunning main lake views, a private dock, fire pit and sandy beach (normal pool), all just minutes from downtown Clarksville. Whether you’re fishing Buggs Island/Kerr Lake, vacationing with family, relaxing on the patio, or checking out the local wineries and brewery, Dockside Dreamz #1 is the perfect escape with all the comforts of home. Sleeps six, Wi-Fi, grill, and a large patio. Discounts available for those also renting Dockside Dreamz #2.

LocationFamilyView

4.95 out of 5 average rating, 110 reviews

The kitchen and dining area features wooden walls and ceiling, complemented by natural light from a window. A spacious kitchen island with bar stools is visible, alongside a dining table surrounded by black chairs. Decor includes mounted deer heads, enhancing the rustic ambiance.

Cabin in Clarksville

Spacious Woodland Cabin - Kerr Lake

Calling all nature lovers, outdoors men, women, & families looking for adventure! Take a hike or enjoy the hot tub. Wooden Cabin close to Clarksville & Bluestone Landing. Take a walk or a golf cart ride to reach the property’s dock or sit on the porch & unwind. Close to everything, yet far away. Enjoy a beautiful cabin w/ modern amenities such as Starlink Internet & smart TVs throughout. Best Wi-Fi you can get -2 bedrooms, 2 full baths, rec room & loft w/4 beds. The perfect place to disconnect.

LocationFamilyAmenities

A wooden dock extends over calm water, featuring a picnic table shaded by a large umbrella. A gentle slope leads to the dock, surrounded by a serene lake landscape and distant tree-covered hills under a partly cloudy sky.

4.92 out of 5 average rating, 141 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.

FamilyValueBathroom

4.91 out of 5 average rating, 240 reviews

A circular firepit made of natural stones is surrounded by a gravel and mulch base, with a crackling fire at its center. The rustic cabin with a metal roof and large windows can be seen in the background, framed by lush greenery.

Home in Farmville

The Inn at Hampden-Sydney

A peaceful, quiet, and cozy home on 36 acres of beautiful land that rests just 5 minutes from Hampden-Sydney College and 10 minutes from Longwood University. We want your stay to be comfortable and relaxing, which is why each bed is comfortable and topped with luxurious linens. The house is equipped with 3 big screen tv's. You can also watch the deer from the enclosed front porch or open back deck. Enjoying sitting around the firepit or walking along one of the many paths on the property.

LocationValueIndoor spaces

4.94 out of 5 average rating, 211 reviews

A charming sunlit cottage nestled on a green lawn, framed by trees. The structure features large windows, maximizing natural light. A patio with a gazebo is visible in the foreground, providing a relaxing outdoor space. The backdrop includes serene surroundings and hints of Kerr Lake.

Cottage in Clarksville

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+).

FamilyLocationRiver

4.96 out of 5 average rating, 282 reviews

Cabin in Blackstone

Rustic Forest Cabin at Whetstone Creek Farm

Unwind in a private mini retreat- enjoy waking up in the king size bed to forest views, birdsong, and a front porch made for sitting! Listen to rain on the tin roof or enjoy a bonfire in the fire pit after taking a stroll down our private wooded trails or wading in the creek. Stay connected with WiFi, or just cozy up with a book or a game. Wildlife abounds on this woodland plant farm. Approximately 15 minutes from downtown Blackstone and Ft. Pickett, this is the perfect place to get away!

FamilyLocationSolo travel

5.0 out of 5 average rating, 10 reviews

A cozy living room features a brown leather sofa adorned with decorative pillows. A green accent chair sits beside a rectangular coffee table, which holds a checkerboard. Large windows allow natural light to fill the space, offering views of the outdoor greenery.

Home in Scottsburg

Cousin Carol's Fishing Adventure! Scottsburg, VA

Welcome to this cozy and fun fishing-themed home at the Little Tin Can Campground! Come rest, relax and enjoy the charming little town of Scottsburg, VA! This retro-inspired home has been comfortably updated and is just minutes away from fishing, hiking and outdoor activities at Staunton River State park; situated closely to South Boston and the Speedway; and about 20-30 min away from several wineries. What's more: inquire about our neighboring property and book a stay full of family fun!

FamilyLocationAccuracy

4.85 out of 5 average rating, 20 reviews

Guesthouse in Keysville

The Cottage at Kentwood

Escape the city life and immerse yourself in the peacefulness of our country retreat. Located at historic “Kentwood”, circa 1837, our cottage offers the perfect blend of charm and comfort. With spacious rooms, a fully equipped kitchen, and cozy living areas, you’ll feel right at home. Unwind on the porch watching the sunset or take a stroll around the property. Centrally located between Raleigh, Richmond, & Lynchburg. Convenient to Farmville, Longwood University, & Hampton Sydney College.

FamilyLocationHospitality

A wooden dock stretches over calm waters, leading into a scenic view of a lake surrounded by green trees. The horizon shows a clear sky with a blend of soft blues and whites, contributing to a peaceful lakeside atmosphere.

5.0 out of 5 average rating, 24 reviews

Red, White & Bluestone - Lake Front, Private Dock

We still have water at our dock! And an XL beach! Make wonderful memories at this thoughtfully outfitted and decorated family-friendly lake front home. Stay in Red, White & Bluestone, located in a charming cove on Buggs Island lake, close to the town of Clarksville (Virginia’s only lakeside town), shops, a brewery, restaurants, and more! The private dock has boat cleats and fishing rod holders and is just steps away, so bring your boat! Bluestone boat landing is just a mile away.

ValueLocationKitchen

Home in Charlotte Court House

A charming two-story farmhouse is set amidst greenery, featuring a metal roof and classic white siding. A covered front porch is showcased, adorned with red chairs, while seasonal foliage adds color to the serene landscape. The spacious yard is littered with fallen leaves.

4.99 out of 5 average rating, 120 reviews

Couples retreat, family getaway, spacious, private

The farmhouse is a wonderful destination for those looking for a quiet place to stay in a farm setting. Surrounded by hayfields, cow pastures, and mature hardwood trees, this third generation home, dating back to 1919, provides ample space for guests to relax and enjoy themselves. Recently renovated using wood cut from the property and farmhouse style decor (Joanna Gaines inspired), this home is the perfect place to get away from the hustle and bustle of everyday life.

FamilyLocationLong stay

4.94 out of 5 average rating, 104 reviews

A spacious porch area is highlighted by three blue rocking chairs, each adding a pop of color against the natural wood decking. A decorative cushion with a paisley pattern sits on one chair, complementing the inviting outdoor space near large windows adorned with soft curtains.

Home in South Boston

Papa's Place at Foy's Farm

Relax with the family, friends, or solo... Welcome to Papa's Place! Our completely renovated 1959 two bedroom one bath home in South Boston VA where rustic meets modern. We invite you to enjoy the large front yard, let the butterflies greet you, watch the deer graze, cherish sunsets from the front porch or late nights by the firepit. Only 26 miles from VIR and 30 from the NEW CEASARS VIRGINIA CASINO!! Come visit Papa's Place... where you will ALWAYS be at home!

ValueLocationAmenities

A private dock is visible extending over the water, featuring two red Adirondack chairs positioned around a small table. Calm lake water can be seen, surrounded by trees and a distant shoreline. A clear sky with scattered clouds completes the serene scene.