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

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.

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.

Barndominium oasis on 22 acres

Get away from it all when you stay under the stars. Enjoy this little one bedroom one bathroom apartment just a short distance from Kerr Lake & Clarkesville. Open the barn doors, grab a beer and enjoy the night fire under the star Happy to host events on the property, just let me know what kind and how many people! Bring your own tents, chairs, tables and have a blast :) Ps. There is no internet available at this time. We do have a lifetime supply of DVDs :) Boats are welcome in the garage!

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+).

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.

Bracey Historic Train Depot

Want to step back in time to the late 1800s? A stay at the historic Bracey Train Depot offers exactly that—plus modern comfort. The Depot is one of the few surviving historic buildings on Bracey Drive, alongside the old post office across the street, the general store next door, and other local landmarks. This stretch of Bracey Drive feels quietly tucked away, just around the “cut,” yet it’s conveniently located less than half a mile from I-85.

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!