Vacation rentals in South Boston

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Top-rated vacation rentals in South Boston

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Guest favorite

Cottage in South Boston

5.0 out of 5 average rating, 110 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!

Dec 5 – 12

G$37,984 GYD per night

Guest favorite

Home in Alton

4.92 out of 5 average rating, 116 reviews

7 mi. to VIR! 18 min to Danville, South Boston, Va

A blend of modern and traditional, this home is under 7 miles from VIR; 18 to Danville, South Boston, or Roxboro. Initial entry reveals an open floor plan combining living, dining, and kitchen areas that are comfortable, spacious, and inviting. Bed and bath spaces are clean, furnished, and stocked with linens, etc; waiting for you to settle in and recharge. Satellite WiFi. Oversized paved parking for guests; very accessible for trailers and/or multiple large vehicles. Strict no smoking or pets

Dec 14 – 21

G$48,922 GYD per night

Guest favorite

Apartment in Rougemont

4.96 out of 5 average rating, 163 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).

Jul 24 – 31

G$19,617 GYD per night

Guest favorite

Home in Semora

4.84 out of 5 average rating, 129 reviews

Scenic Semora Home

This older family home is located in Semora on our family's farm. The home is very secluded and private on a beautiful road. VIR (Virginia International Raceway) is only a 12 minute drive away. Hyco Lake is an 11 minute drive. This makes us perfectly situated between two popular vacation spots. We are about 12 minutes from Milton and 20 minutes from Yanceyville and Roxboro where you can find shopping and restaurants. **Please note this is a very rural home. We do not do long term renters.

Oct 7 – 14

G$22,394 GYD per night

Guest favorite

Cottage in Clarksville

4.91 out of 5 average rating, 138 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+).

May 30 – Jun 6

G$33,586 GYD per night

Guest favorite

Home in Halifax

4.97 out of 5 average rating, 33 reviews

Tay's House

Enjoy a beautiful and quiet countryside retreat. The 1920's era farm house is perched perfectly upon 35 acres of rolling hills located in the south central part of Virginia. The property is adorned with established trees, picturesque views, and unbelievable wildlife. Don't let the rustic charm fool you. The house itself is equipped with fiber optic internet, updated kitchen and living spaces, a remote-controlled gas fire place , a designated office space, and a privately fenced backyard.

Oct 23 – 30

G$31,185 GYD per night

Guest favorite

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!

Sep 7 – 14

G$95,918 GYD per night

Guest favorite

Cabin in Roxboro

4.87 out of 5 average rating, 147 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

Jan 28 – Feb 4

G$27,883 GYD per night

Guest favorite

Cabin in Brookneal

4.9 out of 5 average rating, 163 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.

Oct 6 – 13

G$14,120 GYD per night

Guest favorite

Tiny home in Chapel Hill

4.93 out of 5 average rating, 601 reviews

Chic Modern Tiny House Nestled in the Trees

This 240 sq ft tiny house is situated on a serene 5 acre wooded property. Its a short drive to Hillsborough (10 min), Chapel Hill (15) and Durham (15). I wanted to create a space where guests can take time to rest and reset. Stylish decor, art-filled walls, and a full list of amenities make for a unique and cozy experience of home away from home. Take a step outside and you'll be surrounded by old hardwood trees and the soothing sounds of nature that make life here so peaceful

Jun 3 – 10

G$23,479 GYD per night

Guest favorite

Cabin in Roxboro

4.93 out of 5 average rating, 103 reviews

Majestic Lakefront Log Cabin in the NC High Plains

Cozy Log Cabin located on Lake Mayo just above Roxboro, North Carolina on Whispering Wolf Ranch. Easy access to a functional floating dock. Great for fishing, swimming, meditating, or to just enjoy nature. Paddle boards and Kayaks can be rented at nearby Mayo Lake Park. Can be used for a private romantic getaway or family retreat. Less than 5 miles from the events held at Lake Mayo Park. PARTIES OR EVENTS ARE NOT ALLOWED!

Jul 23 – 30

G$44,497 GYD per night

Guest favorite

Guest suite in Roxboro

4.95 out of 5 average rating, 201 reviews

Mayo Lake Front Spilt Unit: Highend,Clean,Updated

Mayo Lake Front Retreat, enjoy the lower unit at this Lake front home. Enjoy swimming, fishing, kayaking, paddle boating, or just starry nights by the fire on your Private patio. Downstairs unit has Private entrance scenic views and everything you need. Launch your boat at nearby Marina and just pull up and leave parked at the dock right outside your door. Satellite tv and WIFI available.

Sep 16 – 23

G$21,418 GYD per night