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
In two months
In three months
In four months

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, (201 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
$182 nightly
The price is $201
Jun 21 - Jun 22
Total with taxes and fees
Cozy Country Cabin quiet country retreat

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, (38 reviews)
"Everything was just perfect. Will be staying here again."
United States
Joshua L.
$226 nightly
The price is $253
Jun 17 - Jun 18
Total with taxes and fees
Country home with beautiful views and access to hiking, biking, and horse trails

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
$178 nightly
The price is $201
Jun 17 - Jun 18
Total with taxes and fees
Quaint 1-bedroom cabin with a loft with AC in Floyd Knobs

Emerald Lake Retreat Charlestown

Emerald Lake Retreat Charlestown
Charlestown
10.0 out of 10, Exceptional, (3 reviews)
"Roomy, clean, nice setting in nice neighborhood."
United States
David P.
$394 nightly
The price is $445
Jun 17 - Jun 18
Total with taxes and fees
Emerald Lake Retreat Charlestown

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.
$255 nightly
The price is $283
Jun 17 - Jun 18
Total with taxes and fees
Moonlit Cottage Near Louisville

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, (165 reviews)
"Great place to stay and feel right at. Home. "
United States
Adam D.
$488 nightly
The price is $552
Jun 28 - Jun 29
Total with taxes and fees
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

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, (4 reviews)
"Beautiful home & I would highly recommend staying there👍👍"
United States
Kenneth
$286 nightly
The price is $320
Jun 17 - Jun 18
Total with taxes and fees
The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

Lakeside Cottage: 1 bed/1 bath

Lakeside Cottage: 1 bed/1 bath
Henryville
$259 nightly
The price is $301
Jun 17 - Jun 18
Total with taxes and fees
Lakeside Cottage: 1 bed/1 bath

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, (16 reviews)
"This place was great. We will be staying here if ever back in the area. "
United States
Michael B.
$275 nightly
The price is $307
Jun 22 - Jun 23
Total with taxes and fees
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

Cozy motor home in Adorable Fredericksburg IN with all amenities inside and out!

Cozy motor home in Adorable Fredericksburg 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.
$179 nightly
The price is $200
Jun 17 - Jun 18
Total with taxes and fees
Cozy motor home in Adorable Fredericksburg IN with all amenities inside and out!

Hope Hill Hideaway - Family Country Retreat in Southern Indiana near Louisville

Hope Hill Hideaway - Family Country Retreat in Southern Indiana near Louisville
Georgetown
10.0 out of 10, Exceptional, (1 review)
"The stay was amazing. We had some issues with the booking, not at all the hosts fault, it was a technical issues and jenni and wyatt were so helpful and stayed in full contact till it was sorted. The property was so cozy and if we were there for a longer stay we would have loved to use the fire pit and hang out in the beautiful natural scenery. We only stayed for two nights and kept busy the entire time but it will definitely be a repeat to stay at the property. Everything was clean....
United States
Nicholas K.
$312 nightly
The price is $353
Jul 1 - Jul 2
Total with taxes and fees
Hope Hill Hideaway - Family Country Retreat in Southern Indiana near Louisville

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, (23 reviews)
"Very nice stay!"
United States
Tammy W.
$140 nightly
The price is $158
Jun 22 - Jun 23
Total with taxes and fees
Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area
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.
Save an average of 15% on thousands of hotels when you're signed in

Top South Boston Hotel Reviews

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?

35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.: This vacation home rental near South Boston offers a selection of games, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, 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.