A winding road through a dense forest with mountains in the background.

South Boston Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for South Boston vacation rentals

A living room with a sofa, a coffee table, and a potted plant.

1. Insta-worthy 2Bd/1Ba Apt | Minutes from Downtown!

Insta-worthy 2Bd/1Ba Apt | Minutes from Downtown!
Danville
10.0 out of 10, Exceptional, (10 reviews)
"Great unit, thoroughly enjoyed staying here."
United States
Joseph M.
The price is CA $141
CA $401 total
includes taxes & fees
Oct 19 - Oct 20
Insta-worthy 2Bd/1Ba Apt | Minutes from Downtown!
A race track with multiple cars, a Coca-Cola advertisement, and a row of houses in the background.

2. Chic Haven: 2b/1bath in the Heart of Danville

Chic Haven: 2b/1bath in the Heart of Danville
Danville
10.0 out of 10, Exceptional, (2 reviews)
"This is a beautiful apartment, it has everything you need to enjoy your business trip. I will definitely stay here again, great location!"
United States
Justin L.
The price is CA $126
CA $386 total
includes taxes & fees
Sep 23 - Sep 24
Chic Haven: 2b/1bath in the Heart of Danville
A modern kitchen with a central island, bar stools, and a dining area with a bench.

3. Charming 4-bedroom 3-bath house on beautiful Hyco Lake with boat dock.

Charming 4-bedroom 3-bath house on beautiful Hyco Lake with boat dock.
Semora
10.0 out of 10, Exceptional, (27 reviews)
"Well furnished and favorite place to stay for time at VIR"
United States
Larry R.
The price is CA $344
CA $612 total
includes taxes & fees
Sep 27 - Sep 28
Charming 4-bedroom 3-bath house on beautiful Hyco Lake with boat dock.
A kitchen with a stainless steel refrigerator, wooden cabinets, a sink, and a door with a 'blessed' sign.

4. The Country Estate #1 Tranquil 1BR estate perfect for a relaxing getaway.

The Country Estate #1 Tranquil 1BR estate perfect for a relaxing getaway.
Danville
The price is CA $180
CA $214 total
includes taxes & fees
Oct 20 - Oct 21
The Country Estate #1 Tranquil 1BR estate perfect for a relaxing getaway.
A dining area with a wooden table, chairs, a chandelier, and a cabinet with decorative items.

5. Located in Historic Old West End. Minutes from the River District and Casino.

Located in Historic Old West End. Minutes from the River District and Casino.
Danville
10.0 out of 10, Exceptional, (54 reviews)
"Nice place ! "
United States
Pattie C.
The price is CA $227
CA $481 total
includes taxes & fees
Sep 30 - Oct 1
Located in Historic Old West End. Minutes from the River District and Casino.
A dining area with a dark wooden table, a chair, a wall clock, a framed picture, and a wall-mounted light fixture.

6. Walking Distance to Casino

Walking Distance to Casino
Danvilel
10.0 out of 10, Exceptional, (28 reviews)
"Room where great, loved the mattress. Definitely had a great night sleep here!"
United States
Brenda
The price is CA $227
CA $710 total
includes taxes & fees
Sep 23 - Sep 24
Walking Distance to Casino
A house by a lake with a snowy landscape and trees in the background.

7. 10 minutes from VIR. Great bass fishing! Rustic cottage on large private pond.

10 minutes from VIR. Great bass fishing! Rustic cottage on large private pond.
Alton
10.0 out of 10, Exceptional, (1 review)
"We came down for an event at VIR. The hosts were fantastic and the home was lovely. Will be back!"
United States
Chris N.
10 minutes from VIR. Great bass fishing! Rustic cottage on large private pond.
A spacious living room with a large TV, a red sofa, and a patterned rug.

8. Iconic Church Turned Unique Stay (Casino/VIR)

Iconic Church Turned Unique Stay (Casino/VIR)
Danville
10.0 out of 10, Exceptional, (13 reviews)
"We really enjoyed our stay!"
United States
Connie R.
The price is CA $457
CA $918 total
includes taxes & fees
Sep 23 - Sep 24
Iconic Church Turned Unique Stay (Casino/VIR)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Boston Hotel Reviews

The Holbrook Hotel

The Holbrook Hotel

8/10 Good
"My room was cute and super clean. The property isn't your ordinary lay-out, and the entrance to the front desk is confusing. I recommend you call ahead a few minutes before arrival if you are arriving after dark. But I really liked my room. I would stay there again."
Vivian 1-night trip
Posted 11 hours ago
The Holbrook Hotel

Find out more about South Boston

Everything you need to know about South Boston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Boston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Boston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Boston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Boston. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Boston vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Boston vacation rentals we have selected for you start as low as CA $401 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Boston rentals

At Expedia, we put the best South Boston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top South Boston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Boston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Boston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find vacation rentals in South Boston?

Yes, we give you a choice of vacation rentals in South Boston near Vaughan St. Park, or you can select a more remote option if you want a relaxing stay. Our travelers say South Boston has a good selection of restaurants. Make sure you have time to check out the local tours and entertainment choices during your trip.

What are some of the best vacation rentals that South Boston has to offer?

H2O-FRONT Chef’s_Kitchen Gig-WiFi DogsOK EV-Charger Alexa: This vacation home rental near South Boston is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in South Boston?

Choose from 3 Expedia vacation rentals in South Boston for a memorable vacation.

What can I see and do in South Boston?

Family-friendly attractions include Vaughan St. Park and North Main Street Park, whereas Hudson Heritage Farms and Constitution Square are a couple of great spots to enjoy the outdoors. South Boston Speedway and South Boston Town Hall are other places to visit while you're in town.

What are vacation rentals like in South Boston?

Vacation rentals are privately owned properties you can reserve for a short or long stay in South Boston. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for small groups.