Default HTG hotel image

South Boston Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for South Boston vacation rentals

Property grounds

1. 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 absolutely loved this property. We found it to be even better than the description and look forward to staying here again!!!"
United States
Van C.
$286 nightly
The price is $320
Sep 28 - Sep 29
Total with taxes and fees
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
Coffee/tea maker, fridge, microwave, oven

2. 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, (42 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.
$244 nightly
The price is $273
Sep 22 - Sep 23
Total with taxes and fees
Country home with beautiful views and access to hiking, biking, and horse trails
Terrace/patio

3. 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.
$162 nightly
The price is $182
Sep 21 - Sep 22
Total with taxes and fees
Cozy Tiny House in Scottsburg
Property grounds

4. Cozy Country Cabin quiet country retreat

Cozy Country Cabin quiet country retreat
Orleans
10.0 out of 10, Exceptional, (212 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
Cozy Country Cabin quiet country retreat
Smart TV, books

5. 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
9.6 out of 10, Exceptional, (5 reviews)
$181 nightly
The price is $204
Sep 24 - Sep 25
Total with taxes and fees
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs
1 bedroom, WiFi (free), bed sheets

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.
$264 nightly
The price is $308
Oct 4 - Oct 5
Total with taxes and fees
Lakeside Cottage: 1 bed/1 bath
Coffee/tea maker, fridge, microwave, oven

7. 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.
$140 nightly
The price is $158
Oct 5 - Oct 6
Total with taxes and fees
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
Living area

8. Quiet Forest Hideaway Near Fredericksburg

Quiet Forest Hideaway Near Fredericksburg
Fredericksburg
9.0 out of 10, Wonderful, (2 reviews)
$321 nightly
The price is $325
Sep 21 - Sep 22
Total with taxes and fees
Quiet Forest Hideaway Near Fredericksburg
Smart TV

9. Cozy motor home in Adorable English IN with all amenities inside and out!

Cozy motor home in Adorable English IN with all amenities inside and out!
Fredericksburg
10.0 out of 10, Exceptional, (1 review)
"Served its purpose for us! cozy, quiet & comfy! If I ever decide to revisit Indiana, I will stay here again!"
United States
Jeremy R.
$191 nightly
The price is $213
Sep 22 - Sep 23
Total with taxes and fees
Cozy motor home in Adorable English IN with all amenities inside and out!
Exterior

10. Lakeside Cabin: 4 bed/2.5 bath

Lakeside Cabin: 4 bed/2.5 bath
Henryville
8.0 out of 10, Very good, (3 reviews)
"The most beautiful and peaceful place we have ever stayed!! It was neat to find out the history and if you have the chance to stay here, DO NOT MISS IT!! if I could have stayed forever I would have. I was sad to leave! Just a very special place!! I’ve stayed in a LOT of different places and none compares!! It was an honor & our dogs absolutely loved the place!! Never seen them so happy and comfortable in a place!!"
United States
Melanie G.
$618 nightly
The price is $721
Sep 21 - Sep 22
Total with taxes and fees
Lakeside Cabin: 4 bed/2.5 bath
Coffee/tea maker, fridge, microwave, oven

11. 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
$286 nightly
The price is $320
Sep 22 - Sep 23
Total with taxes and fees
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
5 bedrooms, desk, WiFi, bed sheets

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

Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden
Henryville
$959 nightly
The price is $1,119
Sep 30 - Oct 1
Total with taxes and fees
Secluded 51-Acre Retreat | 2 Cabins, Pond & Garden
Terrace/patio

13. 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.
$1,497 nightly
The price is $1,614
Sep 28 - Sep 29
Total with taxes and fees
Star Ridge | Private Estate | Sleeps 20 | Hot Tub
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Boston Hotel Reviews

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

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

10/10 Excellent
"Great place! Would love to rent again."
Tyler A. 2-night trip
Posted 13 hours ago
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit South Boston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $158 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.