Holiday houses in Skipwith

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.

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.

The Tiny House at Wishing Creek

Escape to our charming tiny house nestled in the heart of nature! Perfect for any peaceful retreat, this beautifully designed space offers all the essentials for a comfortable stay, including a cozy bed, fully equipped kitchenette, and modern bathroom. Relax on the outdoor deck and enjoy the serene surroundings. Whether you're seeking a romantic getaway or a solo adventure, our tiny house provides the perfect blend of simplicity and comfort. Close to hiking trails, local attractions, and more!

Dockside Dreamz #2 w/beach & dock

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

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+).

Lakefront Retreat | Private Dock + Sunset Views

Experience the beauty of Buggs Island Lake at this beautiful lakefront retreat! This stunning cottage boasts a private dock and spacious deck, perfect for enjoying sunsets over the lake. Tandem kayaks are included for your water adventures, and a campfire on the beach is the perfect way to end your day with family and friends. With high-speed internet, you can stay connected during your stay. Don't miss out on the expansive views of the lake offered at this property, book your stay today!

Hunter's Haven

Hunter’s Haven is a lovely 800 square foot hide-out property on Kerr Lake in Henderson, North Carolina. Hidden in a wooded cove with access to hunting. There's even a deer stand on the property! Enough room for 4 - 6 adults. There is ample parking. If you want to bring more guests, check out Hunter's Hideaway on AirBNB! It sleeps an additional 4 people and is adjacent to Hunter's Haven. The property is 3 miles from Henderson Point Recreation. Relax at this peaceful place to stay.

The Lucky Leah - Charming Home in Downtown Halifax

Welcome to the Lucky Leah! Enjoy this newly renovated home built in 1900 located in the heart of Historic Downtown Halifax. The flow and function of this home will work for families of all sizes. This home sleeps 6 guests and features spacious 2 Bedrooms 2 Bathrooms including a queen size sleeper sofa . Only footsteps away from Molasses Grill and a short drive to Tunnel Creek Vineyards, Factory Street Brewing, and Springfield Distillery, and located only 20 miles from VIR.

Rooted In Love

Kerr Lake: cozy, super-cute cabin, w/private lake access in neighborhood less than half mile away. Upstairs bedroom, open LR/kitchenette, one bath, in rural VA. Two-burner cooktop & tiny oven (no dishwasher), plus w&d. King bed, plus a daybed w/pop-up trundle in loft; queen foldout sofa downstairs. Strong wi-fi. Boat parking/fish cleaning station. Fenced in dog-run for well-behaved dog. Hammock, firepit & picnic table lakeside! Front porch for sunset and star viewing!

The Silo at Lake Front Winery

The design of our silo embraces the cylinder shape using it for multilevel living. There is an open kitchen that flows into the dining area with modern appliances and fixtures. Fully furnished. One bathroom that is fully functional, stylish and elements that complement the silo character. The silo sits on a winery and overlooks a farm on one side and the vineyard on the next. Located about 5-10 minutes to Clarksville, VA and 15-20 minutes from South Boston, VA.

Kerr Lake Escape | Dock + Beach Access

One of the few Kerr Lake rentals located right in Clarksville. Party in Slow Motion is a beautifully decorated 3BR/2BA lake cottage near Clarksville with views of Buggs Island/Kerr Lake. Located just one row back from the water, it’s an easy ~100 yard walk to our private slip dock and quiet beach access in a calm cove. Two kayaks are included for exploring the lake. Ideal for families, fishermen, and small groups, with high-speed Wi-Fi and air conditioning.

Charming Cove Hideaway

Make some wonderful memories at this unique, fully renovated and family-friendly home! Welcome to the Charming Cove Hideaway in Clarksville, where you are close to the lake, cute shops, the brewery and much more! Longwood Park Lake Access is less than a 2 min drive! Here you can launch your boat and spend the day on the lake; or if you want to splash around, Longwood Park is the perfect place for everyone offering a playground and beach area for swimming!