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Vacation rentals in South Boston

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for South Boston vacation rentals

Other great vacation rentals in South Boston

Top guest favorite
Farm stay in Long Island
5 out of 5 average rating, 47 reviews

Farm Glamping 1 room cabin sleeps 4

RobertRating, 5 stars2 months ago
The farm is a great place to visit, especially for kids. It's a quiet and beautiful area with an absolutely wonderful family running the farm. Sheila and James were extremely hospitable and welcoming. The animals, from dogs to goats to sheep are numerous and fun to watch and be around. I can't wait to go back!
Top guest favorite
Home in Clarksville
4.97 out of 5 average rating, 67 reviews

Country Living near Buggs Island/Kerr Lake

WendyRating, 5 stars3 weeks ago
We love it here. We have stayed twice before and is always our first choice when coming into town.
Guest favorite
Home in Leasburg
5 out of 5 average rating, 19 reviews

New Listing! - Lakefront Cottage

RyanRating, 5 stars3 weeks ago
We had an amazing stay by the lake! The location was absolutely perfect—peaceful, scenic, and relaxing. The house was clean, cozy, and had everything we needed for a comfortable stay. Our host was responsive, accommodating, and made check-in seamless. We highly recommend this spot and can't wait to return!
Top guest favorite
Home in Buffalo Junction
5 out of 5 average rating, 16 reviews

Beautiful LakeHome, Private Dock

TraceyRating, 5 stars3 weeks ago
House was beautiful and we enjoyed our stay!
Superhost
Home in Halifax
4.67 out of 5 average rating, 24 reviews

Bannister Farm

JoshRating, 5 stars2 months ago
This house is amazing! I recently had a long term stay here and the house is beautiful! It has everything needed to serve as a home away from home. The heat works very well in the winter despite the house’s age, and in the warmer months the AC units do a good job of keeping the living areas cool. The surrounding area is quiet, peaceful, and very safe. Teel was an awesome host who went out of her way to make sure my stay was comfortable. She even gave me her personal number to make sure I could keep in contact with her with any potential issues I had. I would definitely stay here again if given the opportunity!
Superhost
Tiny home in Rougemont
4.8 out of 5 average rating, 20 reviews

Small Castle Cottage

KylieRating, 5 stars2 months ago
I stayed at Anabela’s cottage for a 12 week clinical rotation and it was perfect! Not only was the house itself everything that I needed, Anabela was wonderful. She regularly checked in on me and made sure I had everything that I needed to be comfortable. Given my long-term stay, I had family and friends that wanted to visit me and Anabela offered up her other properties next door for them to stay in — free! She is a wonderful hostess and certainly has the gift of hospitality. It was a blessing to have her as my host for 12 weeks and I’m happy to now call her my friend.
Top guest favorite
Home in Gretna
5 out of 5 average rating, 68 reviews

Little Haven Cottage

EricaRating, 5 stars3 weeks ago
We absolutely loved staying in this secluded beautiful house! The fire pit was amazing, and we loved the decor! It was quiet, and peaceful. Perfect for a getaway from the city with children. We took our 2 year old who loves to be outside and we genuinely felt safe and secure in this home. We already booked again! Absolutely wonderful! The hosts were so nice, and had great communication! They had so much on hand items that so many people don’t think to have. She even had pads and tampons for guests, just in case! I loved that so much. Especially for young children, if you have toddlers it’s a great stay! You don’t even need to bring a pack and play. They have one for you! Thank you so much for letting us stay at your wonderful home! We can’t wait to come back!
Guest favorite
Guest suite in Chatham
4.96 out of 5 average rating, 80 reviews

Mahalo Suite...beach vibes in Virginia foothills

MariaRating, 5 stars2 weeks ago
I stayed here for one night and had a wonderful experience. The place was clean, peaceful, and easy to settle into. Communication with the owners was smooth and hassle-free. I especially loved the beautiful backyard, it was a perfect spot to relax.

Quick stats about vacation rentals in South Boston

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 before taxes and fees

  • Total number of reviews

    200 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Gym, BBQ grill, and Laptop-friendly workspace

Frequently Asked Questions

  • 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.

  • Are there vacation rentals with a dedicated workspace in South Boston?

    Yes! Work meets play with ease at over 10 vacation rentals in South Boston featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Halifax County
  5. South Boston