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South Boston Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for South Boston vacation rentals

A covered patio with a door, two wicker chairs, and string lights.

1. Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.6 out of 10, Exceptional, (8 reviews)
"Great location nice place comfortable "
United States
Hipolito C.
The price is CA $149
CA $287 total
includes taxes & fees
Oct 24 - Oct 25
Cozy Tiny House in Scottsburg
A compact kitchen with a refrigerator, microwave, stove, and sink. There is a dining table with chairs and a patterned rug.

2. Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
Memphis
10.0 out of 10, Exceptional, (27 reviews)
"Great host and a great location!"
United States
P a.
The price is CA $135
CA $225 total
includes taxes & fees
Oct 30 - Oct 31
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
A brick building with a central entrance, a small porch, and a pathway leading to the entrance.

3. The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
Salem
9.6 out of 10, Exceptional, (9 reviews)
"We really enjoyed our stay at the Lanning house. It was a very clean and comfortable place to stay. We enjoyed the history of the home as well."
United States
Andrew H.
The price is CA $214
CA $454 total
includes taxes & fees
Oct 6 - Oct 7
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
A modern kitchen with white cabinets, a large island with bar stools, a built-in oven, and a stainless steel refrigerator.

4. Country home with beautiful views and access to hiking, biking, and horse trails

Country home with beautiful views and access to hiking, biking, and horse trails
Henryville
9.8 out of 10, Exceptional, (43 reviews)
"Loved the dog-friendly house that even had a nice small fenced in area. Super quiet and close to the Knobstone trail for some exploring. The house was easy to find and access and the host was friendly. Thanks for the great place to stay!"
United States
Forrest K.
The price is CA $235
CA $406 total
includes taxes & fees
Oct 4 - Oct 5
Country home with beautiful views and access to hiking, biking, and horse trails
A rustic cabin by a pond with a grassy area and trees in the background.

5. Cozy Country Cabin quiet country retreat

Cozy Country Cabin quiet country retreat
Orleans
10.0 out of 10, Exceptional, (215 reviews)
"Great quiet get away in the country Watch deer hummingbirds chipmunk from the porch Feed fish Bloomington not far for a steak dinner Spring mill park for hiking"
United States
Pamela
The price is CA $178
CA $294 total
includes taxes & fees
Oct 22 - Oct 23
Cozy Country Cabin quiet country retreat
A room with a bed, two armchairs, a small table, and a microwave.

6. Lakeside Cottage: 1 bed/1 bath

Lakeside Cottage: 1 bed/1 bath
Henryville
10.0 out of 10, Exceptional, (1 review)
"Awesome place in a gated property. The tiny home is exactly as pictured. Will 100% stay here again for future Henryville visits to see family."
United States
Jonathan B.
The price is CA $191
CA $441 total
includes taxes & fees
Oct 5 - Oct 6
Lakeside Cottage: 1 bed/1 bath
A rustic cabin interior with a stone fireplace, wooden beams, a green sofa, and a television.

7. Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs

Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs
Floyd knobs
9.0 out of 10, Wonderful, (8 reviews)
"Stairs were steep and not for the faint of heart. Cobwebs everywhere. Kitchen did not have basics - e.g., baking sheet, salt, pepper, etc. Sheets frayed and all linens needed replaced."
United States
David
The price is CA $224
CA $285 total
includes taxes & fees
Oct 10 - Oct 11
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs
A rustic cabin with a porch, stone walls, and an American flag.

8. Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Henryville
10.0 out of 10, Exceptional, (173 reviews)
"Great host, clean house in a great location. We really enjoyed our stay."
United States
Michael S.
The price is CA $292
CA $687 total
includes taxes & fees
Oct 5 - Oct 6
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
A cozy living room with a brown sofa, a small side table with a lamp, a potted plant, and a patterned rug.

9. Quiet Forest Hideaway Near Fredericksburg

Quiet Forest Hideaway Near Fredericksburg
Fredericksburg
9.0 out of 10, Wonderful, (2 reviews)
The price is CA $291
CA $466 total
includes taxes & fees
Oct 5 - Oct 6
Quiet Forest Hideaway Near Fredericksburg
A modern kitchen with a central island, black cabinets, a microwave, and a stove.

10. Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
Vallonia
10.0 out of 10, Exceptional, (18 reviews)
"Outstanding place to stay. Plenty of peace and quiet but still not too far from groceries and gas."
United States
James
The price is CA $294
CA $484 total
includes taxes & fees
Oct 5 - Oct 6
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
A large house with a covered patio area featuring outdoor seating and a fire pit.

11. Star Ridge | Private Estate | Sleeps 20 | Hot Tub

Star Ridge | Private Estate | Sleeps 20 | Hot Tub
Wood Township
10.0 out of 10, Exceptional, (8 reviews)
"Really great to have our annual family reunion here for the second time! Such a great place for multigenerational fun! John is a wonderful host!"
United States
martha u.
The price is CA $1,262
CA $2,617 total
includes taxes & fees
Oct 4 - Oct 5
Star Ridge | Private Estate | Sleeps 20 | Hot Tub
A white bedroom with a large bed, a wooden nightstand, and a wall-mounted lamp.

12. Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden

Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden
Henryville
The price is CA $699
CA $1,593 total
includes taxes & fees
Nov 2 - Nov 3
Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden
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

HavenPointe Inn & Suites

HavenPointe Inn & Suites

10/10 Excellent
"The shower could use handrails as the floor seemed slick. We put a towel down on the shower floor and everything was fine."
John 1-night trip
Posted 17 hours ago
HavenPointe Inn & Suites

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 $225 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 a vacation rental in South Boston?

Yes, we give you a choice of vacation rentals close to well known sights in South Boston, or you can choose a more remote option if you're looking for a relaxing stay.

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

Star Ridge | Private Estate | Sleeps 20 | Hot Tub: This vacation home rental near South Boston is located in the mountains and has a balcony, a pool table, and air-conditioning to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in South Boston?

Explore the area and family-friendly sights such as Kentuckiana Trading, or get out into nature at a spot like Deam Lake State Recreation Area. Champions Pointe Golf Club and Huber’s Orchard, Winery & Vineyards are a couple of places you'll find in the larger area.

What are vacation rentals like in South Boston?

Vacation rentals are private properties you can book for several days or more in South Boston. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.