Vacation rentals in Skipwith

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Top-rated vacation rentals in Skipwith

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Guest favorite
A cozy living area is presented with wooden walls and ceiling, featuring a comfortable sofa and a coffee table. A dining table with checkered tablecloth is visible beside the sofa. Wall art depicting a serene landscape is hung, accompanied by a clock and welcoming text.
Cabin in Kenbridge
4.96 out of 5 average rating, 123 reviews

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

Guest favorite
The living area features a large window with sliding glass doors, allowing natural light to fill the space. A comfortable sofa and coffee table are positioned beside a dining area with chairs. A ceiling fan and subtle grey walls complement the wooden floor, enhancing the atmosphere.
Apartment in Clarksville
4.98 out of 5 average rating, 124 reviews

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.

Guest favorite
A serene view of Kerr Lake is displayed, with sunlight glimmering on the gentle waves. Bare trees outline the shoreline, while a distant dock is visible against the clear sky, contributing to the tranquil lakeside scenery.
Home in Clarksville
4.91 out of 5 average rating, 161 reviews

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

Guest favorite
A tiny home is visible amidst a snow-covered landscape, featuring red-framed windows that contrast with the surrounding white. Snow-dusted trees frame the structure, while a set of wooden steps leads to the entrance. The peaceful scene showcases the quiet beauty of winter.
Tiny home in Norlina
4.95 out of 5 average rating, 187 reviews

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.

Guest favorite
The exterior of a modern A-Frame cabin is framed by trees, featuring a striking triangular window that reflects warm light. A welcoming entrance is highlighted by a wooden door, while two outdoor chairs are positioned on a gravel patio, inviting relaxation.
Cottage in Warren County
4.85 out of 5 average rating, 158 reviews

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.

Top guest favorite
The exterior of the lakefront home is shown, featuring a large wooden deck with a central umbrella and a sloped entryway. Tall windows allow natural light to fill the interior. Surrounding trees provide a sense of seclusion and tranquility.
Home in Clarksville
4.94 out of 5 average rating, 127 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.

Top guest favorite
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.
Home in Clarksville
5 out of 5 average rating, 14 reviews

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!

Top guest favorite
A newly built guest house is nestled among greenery, featuring wood plank siding and a covered front porch. Tall grass sways gently in the foreground, while trees frame the background, enhancing the house's secluded atmosphere.
Cabin in Warrenton
5 out of 5 average rating, 148 reviews

Historic Warrenton Small Cabin

Beautiful guest house, located steps from the main house, hidden from public. The cabin is tucked away in our manicure backyard. Spacious fenced in yard where your fur babies can run free. Enjoy the large pergola with comfy seating for nighttime relaxation or dining. The house offers a living room, kitchenette (NO STOVE) and spacious bathroom. The second floor is a large LOFT with a dividing wall separating the two sleeping areas. There are 13 steps to the second floor. ABSOLUTELY NO PARTY!

Top guest favorite
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
4.93 out of 5 average rating, 192 reviews

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+).

Guest favorite
The outdoor patio features a spacious area with a circular seating arrangement and a dining table surrounded by comfortable chairs. A cozy sofa set is arranged on one side, and string lights are strung overhead, enhancing the natural setting of trees in the background.
Cottage in Bracey
4.93 out of 5 average rating, 138 reviews

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.

Top guest favorite
The exterior of the silo is showcased, featuring a cylindrical shape with silver metal siding. A wooden awning covers the entrance, and a concrete path leads to the door. Surrounding gravel adds to the rustic setting, with trees visible in the background under a clear blue sky.
Cycladic home in Buffalo Junction
4.94 out of 5 average rating, 31 reviews

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.

Top guest favorite
A red brick house is set amidst a grassy yard, featuring green shrubs and small trees. The structure has white window trim and black awnings over the windows. A covered porch is seen on one side, enhancing the outdoor space with shade.
Home in Clarksville
4.97 out of 5 average rating, 71 reviews

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.

Popular amenities for Skipwith vacation rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Mecklenburg County
  5. Skipwith