South Boston Vacation Rentals

  • Plan, book, stay with confidence

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

Browse Select South Boston Vacation Homes

Cozy home located close to Louisville that features 2 separate living areas.
Fridge, microwave, oven, stovetop

Cozy home located close to Louisville that features 2 separate living areas.

10.0 out of 10, Exceptional, (4)
"Loved the number of bedrooms, both upstairs (with kitchenette) and on the first floor, great options. Host very responsive to any questions providing great help when needed for 80+ year old Mom and sister on crutches. Would recommend this home to anyone! A little outside New Albany in Greenville, IN, but close to shops. Thanks to the hosts!"
The price is CA $173
CA $500 total
includes taxes & fees
Dec 31 - Jan 1, 2025
Cozy home located close to Louisville that features 2 separate living areas.
Country home with beautiful views and access to hiking, biking and horse trails.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (17)
"We had a short stay to visit some distilleries on our way to the Smokies. It was a clean, quiet, beautiful stay in the country. The only thing I would mention is the numerous plug-ins were overwhelming to the point that we unplugged them while there. Otherwise, great stay!"
The price is CA $238
CA $392 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Country home with beautiful views and access to hiking, biking and horse trails.
Relaxing Country Getaway
Interior

Relaxing Country Getaway

9.6 out of 10, Exceptional, (27)
"The photos of this property I feel like do not give it justice at all. This property is absolutely stunning!!!!!! The shower was super cozy and warm, the beds were very comfortable, and the all-around atmosphere was incredible. I came to this little getaway a girlfriend but left a fiancée! It was the perfect location For an intimate, beautiful proposal. There is a Keurig for convenience, and plenty of pillows and blankets around the cabin. The hot tub was the highlight of my stay. It is in The...
Relaxing Country Getaway
Private Country Getaway 20 minutes from downtown Louisville, KY
Fridge, microwave, oven, stovetop

Private Country Getaway 20 minutes from downtown Louisville, KY

10.0 out of 10, Exceptional, (31)
"Property was exactly as shown. Great location, easy to get to. Beautiful home, we enjoyed the pool which was clean & easy to manage. Loved having a gas grill & not having to mess with charcoal. Bathrooms were clean & updated, comfortable beds. Overall an enjoyable stay. Thank you "
Private Country Getaway 20 minutes from downtown Louisville, KY
Mountain views 15 miles from Louisville. Sleeps 20
Fridge, microwave, oven, stovetop

Mountain views 15 miles from Louisville. Sleeps 20

10.0 out of 10, Exceptional, (4)
"Garage with so many activities is the selling point and completely worth it. So many beds, I think more than advertised. Contact the owner prior to stay as some things were not easy to find or may not have been there, but overall the house served its purpose for a bachelor party."
Mountain views 15 miles from Louisville. Sleeps 20
2600 SF home 15 Minutes from Downtown Louisville in New Albany. Full basement.
Fridge, microwave, oven, stovetop

2600 SF home 15 Minutes from Downtown Louisville in New Albany. Full basement.

9.4 out of 10, Exceptional, (9)
"This house was amazing and in a quiet neighborhood. It was a well worth stay."
The price is CA $180
CA $505 total
includes taxes & fees
Dec 30 - Dec 31
2600 SF home 15 Minutes from Downtown Louisville in New Albany. Full basement.
35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.
Interior

35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.

10.0 out of 10, Exceptional, (12)
"Everything about this place is amazing. 7 of us stayed here for 5 days and there were times you couldn't even tell anyone else was in the house with you. Quiet, comfortable, and peaceful!!! To top it off, the host "Donnie" is fantastic and goes out of his way to make sure your stay is great, and you have everything you need!!!"
35 min to Louisville, 45 to Churchill Downs. Indoor Basketball court.
Pet-Friendly Emerald Lake Retreat in Charlestown!
Miscellaneous

Pet-Friendly Emerald Lake Retreat in Charlestown!

10.0 out of 10, Exceptional, (4)
"We came to the area to see Louisville attractions and chose the home for the space and yard. It's a very spacious home - main bed and bath on one side, three bedrooms and bath on the other side - perfect for giving everyone quiet and space! One level with a few short steps to get in and out. Big driveway. Fabulous closed in porch for watching wildlife. Great fire pit, kitchen and lots of table space for all. Owner was lovely and communicated well. We enjoyed local businesses including bluegrass...
Pet-Friendly Emerald Lake Retreat in Charlestown!
Tell your family to meet you here!<br>No Drinking Parties
Exterior

Tell your family to meet you here!<br>No Drinking Parties

10.0 out of 10, Exceptional, (33)
"Great"
The price is CA $431
CA $914 total
includes taxes & fees
Dec 30 - Dec 31
Tell your family to meet you here!<br>No Drinking Parties
Inviting home with pool table, firepit, central AC, full kitchen, & W/D
Fridge, microwave, oven, stovetop

Inviting home with pool table, firepit, central AC, full kitchen, & W/D

10.0 out of 10, Exceptional, (1)
Inviting home with pool table, firepit, central AC, full kitchen, & W/D
Spacious 3 BR Ranch House W/Patio Yard in a quiet Suburb
Interior

Spacious 3 BR Ranch House W/Patio Yard in a quiet Suburb

9.8 out of 10, Exceptional, (8)
"Home is in a nice quite neighborhood, upon arrival was a littler thrown off by the yard not being mowed. But once inside the home was clean and modern, previous tenants left trash in the garage which you could smell. But once I informed the home owner they came and got rid of it in a timely manner and was ver responsive to all my messages. Everything was clean and newer in home. Good stay and pretty close to food and attractions, would definitely stay again."
Spacious 3 BR Ranch House W/Patio Yard in a quiet Suburb
Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb
Interior detail

Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb

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,"
The price is CA $193
CA $507 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb
All About Alden in Sellersburg, IN
Outdoor dining

All About Alden in Sellersburg, IN

10.0 out of 10, Exceptional, (2)
"We were in Sellersburg for a golf tournament at Covered Bridge. This house is conveniently located near the golf course. The property owner is very good! I will stay here again when I am in southern indiana. "
The price is CA $150
CA $275 total
includes taxes & fees
Jan 6 - Jan 7, 2025
All About Alden in Sellersburg, IN
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
Exterior

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

2.0 star property
10.0 out of 10, Exceptional, (6)
"Wonderful Host and property."
The price is CA $216
CA $368 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Updated Getaway in the hills of southern Indiana. Minutes from Starve Hollow SRA
Do Derby Right! Beautiful 5-bedroom house with pool, hot tub and gym.
Terrace/patio

Do Derby Right! Beautiful 5-bedroom house with pool, hot tub and gym.

Do Derby Right! Beautiful 5-bedroom house with pool, hot tub and gym.
Suburban Staycation
Living area

Suburban Staycation

Suburban Staycation
Derby 2022
Exterior

Derby 2022

Derby 2022
Derby House & Indoor Pickleball
Fridge, microwave, oven, stovetop

Derby House & Indoor Pickleball

2.0 star property
Derby House & Indoor Pickleball
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.
Don't see what you're looking for?
See all available properties in South Boston
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in South Boston

Cozy Country Cabin quiet country retreat
Property grounds

Cozy Country Cabin quiet country retreat

10.0 out of 10, Exceptional, (165)
"It was our second time at the cozy cabin. We love it there. The cabin is so cute and since we love to fish, the pond is our recreation. Highly recommend it if you want a quiet getaway to unplug from tv and WiFi for a bit. "
The price is CA $200
CA $320 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Cozy Country Cabin quiet country retreat
Private Country Getaway 20 minutes from downtown Louisville, KY
Fridge, microwave, oven, stovetop

Private Country Getaway 20 minutes from downtown Louisville, KY

10.0 out of 10, Exceptional, (31)
"Property was exactly as shown. Great location, easy to get to. Beautiful home, we enjoyed the pool which was clean & easy to manage. Loved having a gas grill & not having to mess with charcoal. Bathrooms were clean & updated, comfortable beds. Overall an enjoyable stay. Thank you "
Private Country Getaway 20 minutes from downtown Louisville, KY
Relaxing Country Getaway
Interior

Relaxing Country Getaway

9.6 out of 10, Exceptional, (27)
"The photos of this property I feel like do not give it justice at all. This property is absolutely stunning!!!!!! The shower was super cozy and warm, the beds were very comfortable, and the all-around atmosphere was incredible. I came to this little getaway a girlfriend but left a fiancée! It was the perfect location For an intimate, beautiful proposal. There is a Keurig for convenience, and plenty of pillows and blankets around the cabin. The hot tub was the highlight of my stay. It is in The...
Relaxing Country Getaway
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.