Holiday rentals in Skipwith

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.

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.

Red, White & Bluestone - Lake Front, Private Dock

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. Boating is the perfect way to spend your time on the lake!

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!

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!

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!

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.

Poppey's Family Lake Home

Relax with the whole family at this peaceful place to stay. We are right on the water in a small cove right off of the main lake. Relax on the dock or catch a variety of fish. We would love to share our home away from home with you. We also have a double air fryer, pots and pans, and a washer and dryer. We also have a dish washer. Towels and Linens will be provided if requested. Guests must wash and return linens.

★ Boutique Guest Stay in Downtown Clarksville ★

Built in the late 1800s, this charming apartment is newly renovated and centrally located in downtown Clarksville (Virginia's only lakefront town!). Styled in a modern cottage inspired design, this home is cozy and functional. Featuring a spacious kitchen, primary bedroom with en-suite, workspaces, and porch overlooking Virginia Avenue, this space is the perfect option for a weekend away or an extended stay.

Perfect Getaway - Waterfront w/ Private Dock

Perfect getaway in this lakefront 2BR/2BA home! Private dock available for your use to enjoy year-round fishing and boating. Explore the quaint town of Clarksville, just 10 minutes away by water or road. Pet friendly. Canoe available for your use! This lakefront house is the perfect retreat for couples, small families, and fishermen! If you like to cook, please help yourself to our herb garden!