South Boston Vacation Rentals

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Our top choices for South Boston vacation rentals

Cozy Country Cabin quiet country retreat

Cozy Country Cabin quiet country retreat
Orleans
10.0 out of 10, Exceptional, (190 reviews)
"We really enjoyed our stay. The cabin is very nice and so is the pond."
United States
Scott H.
The price is CA $153
CA $261 total
includes taxes & fees
Feb 16 - Feb 17
Cozy Country Cabin quiet country retreat

Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg
Scottsburg
9.4 out of 10, Exceptional, (6 reviews)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is CA $117
CA $245 total
includes taxes & fees
Mar 3 - Mar 4
Cozy Tiny House in Scottsburg

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, (14 reviews)
"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 CA $129
CA $215 total
includes taxes & fees
Feb 16 - Feb 17
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

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
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home & I would highly recommend staying there👍👍"
United States
Kenneth
The price is CA $200
CA $428 total
includes taxes & fees
Feb 17 - Feb 18
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

Moonlit Cottage Near Louisville

Moonlit Cottage Near Louisville
Palmyra
6.0 out of 10, (1 review)
"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 CA $79
CA $358 total
includes taxes & fees
Feb 16 - Feb 17
Moonlit Cottage Near Louisville

Sleeps 4, secluded, tiny home

Sleeps 4, secluded, tiny home
Fredericksburg
The price is CA $113
CA $276 total
includes taxes & fees
Feb 16 - Feb 17
Sleeps 4, secluded, tiny home

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
10.0 out of 10, Exceptional, (34 reviews)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
The price is CA $202
CA $342 total
includes taxes & fees
Feb 26 - Feb 27
Country home with beautiful views and access to hiking, biking, and horse trails

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, (14 reviews)
"Excellent place to stay. Everything was absolutely amazing. "
United States
Jimmy
The price is CA $238
CA $408 total
includes taxes & fees
Feb 14 - Feb 15
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

Lakeside Cottage: 1 bed/1 bath

Lakeside Cottage: 1 bed/1 bath
Henryville
The price is CA $175
CA $412 total
includes taxes & fees
Feb 15 - Feb 16
Lakeside Cottage: 1 bed/1 bath

Lakeside Cabin: 4 bed/2.5 bath

Lakeside Cabin: 4 bed/2.5 bath
Henryville
The price is CA $365
CA $835 total
includes taxes & fees
Feb 16 - Feb 17
Lakeside Cabin: 4 bed/2.5 bath

Cozy 1-bedroom apartment in wonderful New Albany with Jacuzzi Hot Tub

Cozy 1-bedroom apartment in wonderful New Albany with Jacuzzi Hot Tub
New Albany
The price is CA $189
CA $285 total
includes taxes & fees
Feb 16 - Feb 17
Cozy 1-bedroom apartment in wonderful New Albany with Jacuzzi Hot Tub

Charming 2-bedroom cottage with WiFi, AC in wonderful New Pekin

Charming 2-bedroom cottage with WiFi, AC in wonderful New Pekin
New Pekin
The price is CA $275
CA $632 total
includes taxes & fees
Feb 15 - Feb 16
Charming 2-bedroom cottage with WiFi, AC in wonderful New Pekin
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

Find out more about South Boston

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with South Boston. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Country home with beautiful views and access to hiking, biking, and horse trails: This vacation home rental near South Boston is located in a rural location and offers a selection of games, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 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.