South Boston Holiday Rentals from €153: Search Short-Term Rentals

Q: What are some of the best holiday rentals that South Boston has to offer?

Star Ridge | Private Estate | Sleeps 20 | Hot Tub : This holiday home rental outside of 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 that you can cook with friends or family.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for South Boston holiday 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

Memphis

P a.

includes taxes & fees

11 Nov - 12 Nov

A rustic cabin by a pond with a grassy area and trees in the background.

2. Cozy Country Cabin quiet country retreat

Orleans

Joe C.

includes taxes & fees

6 Dec - 7 Dec

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

Salem

Nina L.

includes taxes & fees

10 Nov - 11 Nov

A room with a bed, two armchairs, a small table, and a microwave.

4. Tiny Lakeside Cottage I 50 Acres of Gardens

Henryville

Jonathan B.

includes taxes & fees

6 Nov - 7 Nov

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

Henryville

Cruze B.

includes taxes & fees

6 Dec - 7 Dec

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

Floyd knobs

Fr. Jay H.

includes taxes & fees

6 Nov - 7 Nov

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

Henryville

Michael S.

includes taxes & fees

11 Nov - 12 Nov

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

Fredericksburg

includes taxes & fees

19 Nov - 20 Nov

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

Henryville

"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!!"

Melanie G.

includes taxes & fees

16 Nov - 17 Nov

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

Vallonia

James

includes taxes & fees

1 Dec - 2 Dec

A spacious living area with a stone fireplace, leather furniture, and a wooden staircase.

11. The Secluded Woodland Retreat | Cabin + Cottage

Henryville

includes taxes & fees

2 Dec - 3 Dec

A large house with a covered patio area featuring outdoor seating and a fire pit.

12. Star Ridge | Private Estate | Sleeps 20 | Hot Tub

Wood Township

martha u.

includes taxes & fees

9 Nov - 10 Nov

View all properties

Find holiday rentals that suit your style

Find out more about South Boston

Everything you need to know about South Boston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Boston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Boston holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Boston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Boston holiday rentals we have selected for you start as low as €153 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Boston rentals

At Expedia, we put the best South Boston holiday 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 holiday.

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 holiday rental in South Boston?

Yes, there are holiday rentals close to the most popular sights in South Boston, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that South Boston has to offer?

Star Ridge | Private Estate | Sleeps 20 | Hot Tub: This holiday home rental outside of 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 that 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 wider area.

What are holiday rentals like in South Boston?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in South Boston. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for small groups.

Holiday Rentals in South Boston

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for South Boston holiday rentals

1. Cozy 2-bedroom basement apartment in charming Memphis IN. with WiFi, office area

2. Cozy Country Cabin quiet country retreat

3. The Lanning House: 3-bedroom house in fabulous downtown Salem with AC

4. Tiny Lakeside Cottage I 50 Acres of Gardens

5. Country home with beautiful views and access to hiking, biking, and horse trails

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

7. Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

8. Quiet Forest Hideaway Near Fredericksburg

9. Enchanting Lakeside Cabin I 50 Acres of Gardens

10. Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA

11. The Secluded Woodland Retreat | Cabin + Cottage

12. Star Ridge | Private Estate | Sleeps 20 | Hot Tub

Find holiday rentals that suit your style

Find out more about South Boston

South Boston holiday rentals: An excellent choice for every season

How to find incredible deals on South Boston rentals

Frequently Asked Questions

Can I find a holiday rental in South Boston?

What are some of the best holiday rentals that South Boston has to offer?

What can I see and do in South Boston?

What are holiday rentals like in South Boston?