Holiday rentals in South Boston

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Top-rated holiday rentals in South Boston

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Guest favourite

Cottage in South Boston

5.0 out of 5 average rating, 113 reviews

Lady in Red

Enjoy this cozy cottage located just minutes from Clarksville/Kerr Lake or downtown South Boston, VA. Nearby attractions include South Boston Speedway, VIR, Fit Club, Heritage Trail, downtown shopping, Busy Bean coffee shop and deli, fine dining at Molasses Grill, or lakeside at the Bridgewater Bar and Grill, Cooper’s Landing, Tunnel Creek Winery, Clarksville Brewery Company, Springfield Distillery, Factory Street Brewery, Blue Creek Cove Donuts, and Dairy Dell old fashioned hotdogs & ice cream!

Guest favourite

Farm stay in Greensboro

4.96 out of 5 average rating, 223 reviews

Arya’s cottage with a loft & jacuzzi

Adults only, 18&older. No smoking or vaping allowed inside or on premises. Up to 2 dogs welcome for an additional fee. Peaceful and centrally-located place. From your loft bedroom overlook beautiful rolling pastures. Take a stroll on our walking trails or through the woods on the 41 acres, read a book, sit around your fire pit, soak in the private jacuzzi, or head 6 miles to downtown for some nightlife. We do offer a tour and interaction with the animals for an additional fee and scheduled time.

Guest favourite

Flat in Rougemont

4.96 out of 5 average rating, 167 reviews

Cozy Rougemont Studio w/Walking Trails - Farm Time

Welcome! Our newly renovated Farm Time studio, with full kitchen, is perfect for a quiet get away. Nestled among a lush treeline and picturesque pond, this 1-bathroom apartment with queen bed and full sleeper sofa, is the perfect place to relax. Spend crisp mornings strolling through the green fields or enjoy a fire overlooking the pond at night. There’s also plenty to do in nearby Hillsborough (10 miles) and Durham (18 miles) - museums, parks, markets, and restaurants. RDU Airport (34 miles).

Guest favourite

Apartment in Moneta

4.98 out of 5 average rating, 194 reviews

Fun Lake Getaway with Breathtaking Views

Fantastic getaway on beautiful Smith Mountain Lake! Enjoy stunning views on two sides of this top-floor, corner condo with a wrap-around deck and natural shade. It is perfect for a relaxing break or an adventure! Activities include boating (with guest docks), swimming (indoor and outdoor), pickle ball, working out, and relaxing in the hot tub, steam room or sauna! If you are working remotely, this quiet space includes a desk and high-speed wireless. The individual HVAC unit also has a UV light.

Guest favourite

Home in Bedford

5.0 out of 5 average rating, 236 reviews

Gateway Cottage. Historic Homeplace+Mountain Views

We have some surprises for you at Gateway Cottage! We hope you'll come share them. It's the historic homeplace for a family of seven who lived here for 100 years. It's now a blend of farmhouse and contemporary. This cottage is also a blend of country and town, with plenty of space to spread out, relax, walk our 3 acres, view mountains, and watch the deer. Need something you might have at home? I bet we've thought of it! You'll be surprised to find how well-equipped Gateway Cottage is.

Guest favourite

Home in Semora

4.99 out of 5 average rating, 101 reviews

Panoramic Lakefront Oasis at Hyco Pointe

Come enjoy everything that lake life has to offer at our oasis, Hyco Pointe! Built in 2004 with 3 bedrooms (master on main floor, two on second floor), our home is located on a pointe that has spectacular views with a secluded feel. Two living spaces with french doors leading to outdoor seating, including screened porch on upper level, large fire pit and grill on bottom hardscape. Gently sloping walkway to spacious dock with access to kayaks and paddle boards. Two smart TV's and WiFi.

Guest favourite

Cottage in Clarksville

4.91 out of 5 average rating, 144 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 favourite

Place to stay in Roxboro

4.99 out of 5 average rating, 321 reviews

Original Midcentury Modern "Glass House on Hyco"

Very unique architecture on Hyco Lake! The glass walls on the main level provide excellent natural lighting! Wood exposed beams, huge glass windows, harwood floors, concrete wood burning fireplace, updated kitchen, huge screened in porch opened to the main living area all add to the beauty of this midcentury modern property. The boat dock provides lake access where the paddle boards and kayaks are available to guests! Miles from VIR raceway and convenient to the Triangle & Triad areas!

Guest favourite

Cabin in Roxboro

4.87 out of 5 average rating, 149 reviews

Water Front Lake House!

Waterfront home on MAYO LAKE. 2 Bd, 1.5 bath fully furnished . Wi-fi, Smart TVs, Direct TV, Alexa, frig, stove washer/dryer, microwave. Queen-size bed, sleeper sofa and bunk bed. Wrap around porch w/ rocking chairs, swing and 2 picnic tables. Large yard for playing, just feet away from the water and dock, hammock and fire pit. Lots of fishing, single kayak, 2 person kayak, canoe and paddle boat available. PERFECT FOR ANY SEASON LONG OR SHORT STAY. Located on Mayo Lake in Roxboro, NC

Guest favourite

Cabin in Brookneal

4.9 out of 5 average rating, 167 reviews

Rustic Cabin on a 350+ acre Camp

This charming rustic cabin is located at Hat Creek Camp, a 350+ acre camp with over 7 miles of hiking trails and two lakes. The cabin has three rooms, a bedroom, bathroom, and common space/kitchen. The kitchen includes a stove, fridge, blender, coffee maker, and microwave. The bedroom has a Queen bed, and the bathroom has a spacious shower. This cabin is small but very personable, around the camp it is affectionately known as The Pickle. Perfect for quiet getaways in the country.

Guest favourite

Home in Henrico

4.94 out of 5 average rating, 174 reviews

Cozy Quail Shores Lake Gaston

Quaint, cozy lake home nestled on 1.4 acres with a fabulous Main Lake view! Open and bright one level floor plan with living room, dining area, kitchen with granite counter tops and eat-in bar, 2BR/1 Bath. Awesome sun room with furniture for enjoying the sunrise over the main lake with your morning coffee. Walk down the beautiful landscaping to a nice sandy beach and boathouse. Absolutely perfect for kayaking, swimming, and boating at your next summer getaway vacation home!

Guest favourite

Cabin in Hillsborough

5.0 out of 5 average rating, 138 reviews

Spacious Poolside Guesthouse on Private Pond

Our 67-acre property, Split Rock, is located 25 min. from Duke University and UNC-Chapel Hill. We are also 15 min. from Carrboro & Hillsborough, a historic, walkable community. Our guesthouse is a large pool cabana with kitchenette & queen bed overlooking a 4.5-acre pond surrounded by uninterrupted woodland. You are welcome to canoe, fish, walk our trails, play disc golf, or just enjoy the peaceful view. Split Rock is ideal for couples and solo travelers.