Holiday houses in South Boston

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Top-rated holiday rentals in South Boston

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Apartment in Danville
4.96 out of 5 average rating, 208 reviews

The Historic Blessing House in Danville on Main

Located on historic Main Street, the home has central HVAC, is workspace friendly, w/ tv and walking distance to coffee shop/wine bar/restaurant/museum/ hospital. Averette Univ is 6 blocks. Casino 1 mi Queen bed, ceiling fan, window blinds, drapes, full floor mirror & walk-in closet. Full kitchen w/ ceiling fan, coffee, tea, Keurig, bottled water, disinfectant, sanitizer, and cooking essentials. Private Bath with shower, soap, shampoo, conditioner, hair dryer. Linens incl. W/D available.

Guest favourite
A white-sided mobile home is shown with a welcoming front porch. A concrete walkway leads to the entry door. Windows are visible, allowing natural light. Green grass surrounds the home, enhancing its connection to the rural landscape.
Home in Semora
4.85 out of 5 average rating, 169 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.

Top Guest favourite
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+).

Top Guest favourite
Cabin in Vinton
4.99 out of 5 average rating, 146 reviews

Forest Cabin Retreat | Hot Tub & Creekside

Welcome to The Cabin! •15 min to the Blue Ridge Parkway •20 min to Smith Mountain Lake •25 min to Downtown Roanoke •40 min to Peaks of Otter Follow our IG @rambleonpines for cabin tours and photos Awaiting guests deep in the poplars that over took this holler years ago after all the green beans and potato crops were pulled from this fertile soil, is a modern chic cabin over looking a babbling creek with all the luxuries one would need for a weekend away from the grind of life.

Guest favourite
Home in Halifax
4.9 out of 5 average rating, 135 reviews

Spencer Hill

Home Away from Home! Spencer Hill features 3 bedrooms, 1 bath, large fully equipped kitchen, family room, and screened in patio. We are centrally located between Historic Downtown Halifax and South Boston minutes to shopping, fine dining and entertainment, Molasses Grill, Berry Hill Plantation, Factory Street Brewing, Springfield Distillery, Tunnel Creek Vineyards, short track racing at South Boston Speedway, 20 mins west is VIR race track, and Clarksville lake is 20 mins east.

Guest favourite
The interior space features a warm wooden ceiling and a large Smart TV mounted on the wall. A glass sliding door offers views of the lush greenery outside and the lake beyond, leading to a deck with outdoor seating.
Home in Leasburg
4.93 out of 5 average rating, 156 reviews

Mountain cabin feel on Hyco Lake.

Unwind at this hidden jewel tucked in the woods on Hyco Lake. Forget tiny houses, this “Skinny House” boasts two bedrooms, two baths, a spacious open floor plan, cedar ceilings, fully equipped kitchen, gas grill, solo stove, laundry room. Indoor and outdoor living that is large enough for six adults. Floating dock invites you to spend your days on the lake - swimming, fishing, boating, or just soaking in the views. Canoe, Kayaks, Paddle-boards & life vests provided!

Top Guest favourite
A rustic log cabin is nestled among lush greenery, surrounded by trees. A grassy yard extends in front, with a vehicle parked nearby. The structure features multiple windows, showcasing its charming facade and creating a sense of tranquility in the natural setting.
Cabin in Keysville
4.98 out of 5 average rating, 148 reviews

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.

Superhost
A spacious bedroom features a king bed with a neatly arranged white quilt. A bedside lamp illuminates the room beside a dark wooden nightstand. Natural light enters through a large window, complemented by soft carpeting underfoot.
Apartment in South Boston
5 out of 5 average rating, 15 reviews

Quiet Downtown Apartment

Quiet upstairs apartment, perfect for long term stays. Spacious rooms are above professional offices below, so your privacy and personal quiet space is ensured. King bed, two large dressers, additional seating and work area make this a terrific space for an individual or couple. Bathroom and dressing area is spacious, with dresser and large closet to make your long term stay feel more like home. Kitchenette includes under counter refrigerator, microwave and Keurig.

Guest favourite
A spacious porch area is highlighted by three blue rocking chairs, each adding a pop of color against the natural wood decking. A decorative cushion with a paisley pattern sits on one chair, complementing the inviting outdoor space near large windows adorned with soft curtains.
Home in South Boston
4.96 out of 5 average rating, 89 reviews

Papa's Place at Foy's Farm

Relax with the family, friends, or solo... Welcome to Papa's Place! Our completely renovated 1959 two bedroom one bath home in South Boston VA where rustic meets modern. We invite you to enjoy the large front yard, let the butterflies greet you, watch the deer graze, cherish sunsets from the front porch or late nights by the firepit. Only 26 miles from VIR and 30 from the NEW CEASARS VIRGINIA CASINO!! Come visit Papa's Place... where you will ALWAYS be at home!

Top Guest favourite
The exterior of a spacious house is shown, featuring a front porch with white railings and a distinct red door. Grass surrounds the gravel driveway leading to the entryway. Large windows are visible on either side of the door, enhancing the facade's symmetry.
Apartment in Concord
4.99 out of 5 average rating, 153 reviews

Hill of Beans

One bedroom, basement apartment in well kept house. The apartment is furnished with antiques and set on the corner of a farm with good views. The apartment has a private entrance and parking just outside the door. We are a retired but active couple who live upstairs. The kitchen has a Keurig coffee maker and is stocked with coffee, tea, coffee fixings, snacks, and light breakfast items. We are 25 minutes to downtown Lynchburg and 20 minutes to Appomattox.

Top Guest favourite
The charming white house with a steep black shingle roof features symmetrical gabled dormers and black shutters on the windows. A wide pathway leads to a welcoming front door, surrounded by a spacious lawn and trees, providing a relaxing outdoor setting.
Home in Halifax
4.98 out of 5 average rating, 55 reviews

"The Guest House of Halifax"

Comfortable 1940s home adjacent to Halifax County Club. Rest, relax and enjoy the local sights or take in 18 holes. Full kitchen. 1st-floor master bedroom/bath [2 steps down]. Basement laundry available. Close to restaurants, outdoor activities and groceries. Enjoy antique shops, farmer's markets, historical sites, sports, waterways & walking paths. Plenty of space for families or out-of-town short-term employees. We look forward to hosting you!

Guest favourite
A cozy living area features a light-colored sofa adorned with decorative pillows, positioned near large windows that invite natural light. A small side table rests beside an accent chair, and a bookshelf filled with books adds a touch of warmth. Soft curtains frame the windows.
Home in South Boston
4.91 out of 5 average rating, 22 reviews

Farm Life, Close to Town

Relax in this beautiful rural setting while remaining super close to town. Fully remodeled, this home has all up to date amenities, stylish furniture and fixtures, cleanliness and tranquility, all within minutes of the most popular attractions in South Boston and Clarksville. Perfect for work or travel, or just to explore a new area for a bit, we welcome you to come and relax on our deck at sunset and see why we love it so much here.

Popular amenities for South Boston holiday rentals

Frequently Asked Questions

  • Do house rentals in South Boston have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in South Boston. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in South Boston?

    Experience the best of South Boston with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for House Rentals in South Boston?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in South Boston have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in South Boston. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in South Boston

  • Total holiday rentals

    Explore 20 holiday rentals in South Boston

  • Nightly prices starting at

    South Boston holiday rentals start at $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 260 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of South Boston holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across South Boston rentals

  • 4.9 Average rating

    South Boston stays are highly rated by guests—averaging 4.9 out of 5!

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