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South Boston Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for South Boston vacation rentals

A compact kitchen with a refrigerator, microwave, stove, and sink. There is a dining table with chairs and a patterned rug.

1. 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, (31 reviews)
"Great host and a great location!"
United States
P a.
$150 nightly
The price is $170
Nov 11 - Nov 12
Total with taxes and fees
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
A wooden deck with a view of a lake and a sign reading "Lake View."

2. Cozy Country Cabin quiet country retreat

Cozy Country Cabin quiet country retreat
Orleans
10.0 out of 10, Exceptional, (217 reviews)
"Great place!"
United States
Joe C.
$178 nightly
The price is $198
Nov 8 - Nov 9
Total with taxes and fees
Cozy Country Cabin quiet country retreat
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
9.8 out of 10, Exceptional, (11 reviews)
"We loved our stay here. It was the perfect location. The house was clean and I would stay here again."
United States
Nina L.
$271 nightly
The price is $304
Nov 10 - Nov 11
Total with taxes and fees
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
A room with a bed, two armchairs, a small table, and a microwave.

4. Tiny Lakeside Cottage I 50 Acres of Gardens

Tiny Lakeside Cottage I 50 Acres of Gardens
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.
$259 nightly
The price is $302
Nov 6 - Nov 7
Total with taxes and fees
Tiny Lakeside Cottage I 50 Acres of Gardens
A modern kitchen with white cabinets, a large island with bar stools, a built-in oven, and a stainless steel refrigerator.

5. 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, (44 reviews)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
$245 nightly
The price is $274
Nov 11 - Nov 12
Total with taxes and fees
Country home with beautiful views and access to hiking, biking, and horse trails
A rustic cabin interior with a stone fireplace, wooden beams, a green sofa, and a television.

6. 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, (10 reviews)
"Great spot for a guys weekend."
United States
Fr. Jay H.
$172 nightly
The price is $194
Nov 6 - Nov 7
Total with taxes and fees
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs
A rustic cabin with a porch, stone walls, and an American flag.

7. 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, (176 reviews)
"Great host, clean house in a great location. We really enjoyed our stay."
United States
Michael S.
$425 nightly
The price is $480
Nov 11 - Nov 12
Total with taxes and fees
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.

8. Quiet Forest Hideaway Near Fredericksburg

Quiet Forest Hideaway Near Fredericksburg
Fredericksburg
9.0 out of 10, Wonderful, (2 reviews)
$335 nightly
The price is $338
Nov 19 - Nov 20
Total with taxes and fees
Quiet Forest Hideaway Near Fredericksburg
A large, multi-story wooden house with a dock extending over a body of water, surrounded by trees.

9. Enchanting Lakeside Cabin I 50 Acres of Gardens

Enchanting Lakeside Cabin I 50 Acres of Gardens
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.
$566 nightly
The price is $661
Nov 16 - Nov 17
Total with taxes and fees
Enchanting Lakeside Cabin I 50 Acres of Gardens
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, (20 reviews)
"Outstanding place to stay. Plenty of peace and quiet but still not too far from groceries and gas."
United States
James
$290 nightly
The price is $325
Dec 1 - Dec 2
Total with taxes and fees
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
A spacious living area with a stone fireplace, leather furniture, and a wooden staircase.

11. The Secluded Woodland Retreat | Cabin + Cottage

The Secluded Woodland Retreat | Cabin + Cottage
Henryville
$933 nightly
The price is $1,089
Dec 1 - Dec 2
Total with taxes and fees
The Secluded Woodland Retreat | Cabin + Cottage
A large house with a covered patio area featuring outdoor seating and a fire pit.

12. 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.
$1,629 nightly
The price is $1,763
Nov 9 - Nov 10
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.
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Top South Boston Hotel Reviews

Knights Inn and Suites Salem

Knights Inn and Suites Salem

10/10 Excellent
"My go-to place to stay when I'm in Salem. The owners are very nice; the rooms are clean and recently remodeled. The bed was super comfortable and I got a great nights sleep!"
James 1-night trip
Posted 1 hour ago
Knights Inn and Suites Salem

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 $170 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.