South Boston Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Vacation Rentals in South Boston

Property grounds
Cozy Country Cabin quiet country retreat

Cabin in Orleans

10.0 out of 10, Exceptional, (187)
"We really enjoyed our stay. The cabin is very nice and so is the pond."
United States
Scott H.
The price is ￥17,475
￥29,743 total
includes taxes & fees
Dec 9 - Dec 10
Cozy Country Cabin quiet country retreat
Smart TV, fireplace, video games, DVD player
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Cabin in Henryville

10.0 out of 10, Exceptional, (153)
"This is beautiful property and thoughtful amenities. The host is super responsive. We cannot wait to plan our next stay. "
United States
Katie A.
The price is ￥34,949
￥74,246 total
includes taxes & fees
Dec 11 - Dec 12
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Fridge, microwave, oven, stovetop
Large Group Rental Near Louisville with Mountain Views

Vacation Home in Wood Township

10.0 out of 10, Exceptional, (6)
"Great location and stunning views!!"
United States
Jeff R.
Large Group Rental Near Louisville with Mountain Views
Property grounds
Cozy Cabin Escape in Borden, IN – Minutes from Louisville & Outdoor Trails

Cabin in Borden

2.0 star property
Cozy Cabin Escape in Borden, IN – Minutes from Louisville & Outdoor Trails
Fridge, microwave, oven, stovetop
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

Apartment in Memphis

10.0 out of 10, Exceptional, (13)
"Property was very clean, smelt great, and spacious. Located in a nice neighborhood. Hosts were extremely accommodating and friendly. Would definitely stay here again if I'm back in the area for an overnight trip. "
United States
Mandy M.
The price is ￥14,756
￥24,573 total
includes taxes & fees
Dec 9 - Dec 10
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
Exterior
Cozy Tiny House in Scottsburg

Vacation Home in Scottsburg

9.4 out of 10, Exceptional, (3)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is ￥12,271
￥26,791 total
includes taxes & fees
Dec 29 - Dec 30
Cozy Tiny House in Scottsburg
Fridge, microwave, oven, stovetop
Country home with beautiful views and access to hiking, biking, and horse trails

Vacation Home in Henryville

10.0 out of 10, Exceptional, (28)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
The price is ￥23,067
￥38,536 total
includes taxes & fees
Dec 10 - Dec 11
Country home with beautiful views and access to hiking, biking, and horse trails
Fridge, microwave, oven, stovetop
Emerald Lake Retreat Charlestown

Vacation Home in Charlestown

10.0 out of 10, Exceptional, (3)
"This a great place for families to gather. It's very spacious and clean and comfortable. And though it's in a quiet and peaceful area with a small lake at the base of the property, places to eat and get groceries are just a short drive away. There's a wonderful seating area around a firepit, too!"
United States
Kelly P.
The price is ￥18,640
￥71,087 total
includes taxes & fees
Dec 12 - Dec 13
Emerald Lake Retreat Charlestown
Pool
5 BR, 4 baths, Pool, HotTub, Family Friendly, near Louisville KY, Private

Vacation Home in Fredericksburg

10.0 out of 10, Exceptional, (118)
"Beautiful place inside and out. Totally loved the stay. "
United States
Tonda A.
5 BR, 4 baths, Pool, HotTub, Family Friendly, near Louisville KY, Private
Fridge, microwave, oven, stovetop
2600 SF home 15 Minutes from Downtown Louisville in New Albany. Full basement.

Vacation Home in New Albany

9.4 out of 10, Exceptional, (10)
"It was a fast stay but super nice and accommodating!"
United States
Rachel P.
2600 SF home 15 Minutes from Downtown Louisville in New Albany. Full basement.
Interior
35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.

Vacation Home in Fredericksburg

9.6 out of 10, Exceptional, (20)
"Excellent place very nice "
United States
Donna G.
35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.
Exterior
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

Vacation Home in Vallonia

2.0 star property
10.0 out of 10, Exceptional, (13)
"Excellent place to stay. Everything was absolutely amazing. "
United States
Jimmy
The price is ￥27,260
￥46,190 total
includes taxes & fees
Dec 9 - Dec 10
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
Interior
Relaxing Country Getaway

Vacation Home in Lexington

9.4 out of 10, Exceptional, (43)
"Very nice. We enjoyed ourselves a lot and would come back! "
United States
Stephanie G.
Relaxing Country Getaway
Exterior detail
Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb

Vacation Home in Sellersburg

4.0 star property
9.4 out of 10, Exceptional, (10)
"Very nice house in a nice neighborhood, spacious home environmental, felt more that at home there,"
United States
Tammy
Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb
Exterior
Tell your family to meet you here!<br>No Drinking Parties

Vacation Home in Hardinsburg

10.0 out of 10, Exceptional, (37)
"We love staying here for our annual Kayak trip!"
United States
Joni D.
The price is ￥41,799
￥93,266 total
includes taxes & fees
Dec 9 - Dec 10
Tell your family to meet you here!<br>No Drinking Parties
Terrace/patio
3BR/3BA Peaceful Retreat - Fire pit & Game room

Vacation Home in Vallonia

3BR/3BA Peaceful Retreat - Fire pit & Game room
Outdoor dining
Moonlit Cottage Near Louisville

Cottage in Palmyra

6.0 out of 10, (1)
"Beautiful land and venue with great location! Absolutely loved those aspects and would’ve given it more stars if there were no concerns. The only issues we had were regarding cleanliness (a very strong mold smell resulting from a kitchen sink leak in the cabinet below) and pest infestations in the kitchen. Both were communicated to the property manager who advised they relayed them to the owners. We made it work as we weren’t at the house much at all, but it would have been very nice to receive...
United Kingdom
Stephanie C.
The price is ￥9,786
￥41,380 total
includes taxes & fees
Dec 12 - Dec 13
Moonlit Cottage Near Louisville
Smart TV, fireplace
Anjuna River House - the hidden Scandi cabin on 12 acres in Southern Indiana!

Cabin in New Pekin

10.0 out of 10, Exceptional, (8)
"Property was very unique to Indiana. Only a couple hours from Indy made it perfect for a weekend getaway. The property was awesome, owners were great to work with, and just an overall good experience. Highly recommend!"
United States
Kolten C.
Anjuna River House - the hidden Scandi cabin on 12 acres in Southern Indiana!
Property grounds
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

Vacation Home in Salem

"This is a lovingly restored historical property with many beautiful original features, like the staircase & railings. The little town is so nice, and the people are friendly. We came down from Georgia to help a family member move into the home they just bought and needed a comfortable place to stay after moving stuff all day. We all decided we need to come for a longer time so we can check out all the interesting historical site nearby. We ate out every day & only used the coffee maker but the...
United States
Elizabeth
The price is ￥24,884
￥51,703 total
includes taxes & fees
Dec 9 - Dec 10
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC
Fridge, microwave, oven, stovetop
Stonecrest 722, Modern 2Bd Apt I Parking I Gym

Apartment in New Albany

Stonecrest 722, Modern 2Bd Apt I Parking I Gym
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

Ramada by Wyndham Sellersburg/Louisville North

Ramada by Wyndham Sellersburg/Louisville North

10/10 Excellent
"Clean room, helpful staff, good breakfast "
Jessica 1-night trip
Posted 5 days ago
Ramada by Wyndham Sellersburg/Louisville North

Find out more about South Boston

Search for holiday rentals in South Boston on Expedia! You can easily find your home rentals, villas, holiday apartments in South Boston using one of the methods below:

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Look no further and take a look at our great range of rental properties in South Boston!

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?

Cozy Tiny House in Scottsburg: This vacation home rental near South Boston has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.