Holiday rentals in Skipwith

The Rustic Retreat

Rest and relax here! Beautiful, cozy little cabin in a rustic, country setting. Watch the sun set over tranquil fields and enjoy deer and other wildlife. Charmingly built and waiting for you! This cabin features: -Fully furnished kitchen -Spacious bedroom with queen bed -1 bathroom (small)(shower) -Beautiful wood throughout, with lots of live-edge charm -Clean and cozy -Wake up to homemade cinnamon rolls and coffee, or choose from a variety of restaurants within 25 minutes or less

Cozy Getaway Efficiency on Buggs Island/Kerr Lake

Fully stocked efficiency on Bluestone Creek, Clarksville, VA. Will sleep 4 (queen bed and sofa sleeper). Best suited for a couple or will accommodate family up to 4. Covered deck overlooking lake. Quiet and secluded, surrounded by 28 acres of woods. Perfect for fishermen and recreation. Parking for boat/ trailer. Dock has electric. A canoe is provided. 15-minute boat ride to Clarksville. Launch is 4 miles from property. Private entrance, 2nd floor. No meals served. Over 10 yrs is an extra guest.

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

Eco Friendly - Tiny Home

The ten year old you will love the queen sized loft. Awesome 170 square foot tiny home nestled in the middle of 20 acres on Matthews Creek Farm. By staying here you help us live more sustainably as we try to repurpose, reduce, reuse and recycle. Our 7 kilowatt grid tie solar system provides almost all of the tiny home’s power. Eco friendly Natures Head compost toilet saves hundreds of gallons of fresh water a year. Experience staying with chickens, goats, cows, geese and a donkey on the farm.

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.

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.

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+).

Cheerful 3-bedroom Cottage in lakeside community

Enjoy family time at the lake and relax in this peaceful cottage that is walking distance to the community beach with a sand volleyball court, basketball court, picnic and playground area. If you have a boat bring it. You will have access to the beach boat ramp. The home has 3 Bedrooms and 2 bathrooms. If you love golf , no problem..the property is part of a country club with a 9 hole golf course (daily fees apply). If you like tennis, tennis courts are also available for a daily fee.

Peaceful Log Cabin in the country (no extra fees)

Hand-Hewn Log Home on 1.5 acres with a newly added outdoor area in Sept 2025. 20 minutes to Pineview, Waverly and Pavilion @Mimosa wedding venues. 5 Minutes from town, 35/40 minutes to Longwood U and Hampden Sydney College. Zero traffic! Plenty of room - 2 bedrooms, fully stocked kitchen, Coffee & Tea Bars. Clean and cozy. The perfect place to unwind, unplug and reset your clock We strive to go beyond expectations designing our cabin the way Airbnb vacations once were.

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.

Country Living near Buggs Island/Kerr Lake

RUSTIC COUNTRY CHARM just minutes away from Buggs Island/Kerr Lake. This 2 bedroom, 1 bath home is perfect for the person/family looking to disconnect and relax for a few days. Surrounded by farmland, you are welcome to take a nature hike around the farm and soak up the beauty. Located 5 minutes from Staunton View Boat Landing and 15 minutes from the Town of Clarksville. During deer hunting season, arrangements can be made to use deer stand on the farm.