
Photo by Hyelsinta
Historic South Hill holiday lettings
We found 115 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Historic South Hill that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the amenities that you need and want for your stay, which might include cable TV and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Historic South Hill
Showing deals for:25 Jul - 1 Aug
Image gallery for Botherum Carriage House, Garden Lovers Delight

1010 out of 10 rating
Exceptional
(10 reviews)
Botherum Carriage House, Garden Lovers Delight
Lexington, KY
8% off
Price is £7,764
£7,764
£1,109 per night
includes taxes & fees
Image gallery for Historical Villa w/hot tub-1block from Rupp

9.09.0 out of 10 rating
Wonderful
(7 reviews)
Historical Villa w/hot tub-1block from Rupp
Lexington, KY
7% off
Price is £8,256
£8,256
£1,179 per night
includes taxes & fees
Image gallery for Upscale downtown Lexington townhome

1010 out of 10 rating
Exceptional
(52 reviews)
Upscale downtown Lexington townhome
Lexington, KY
7% off
Price is £4,842
£4,842
£692 per night
includes taxes & fees
Image gallery for NEW Chevy Chase-1mi to Rupp-Kroger Field-Downtown

9.89.8 out of 10 rating
Exceptional
(6 reviews)
NEW Chevy Chase-1mi to Rupp-Kroger Field-Downtown
Lexington, KY
7% off
Price is £1,758
£1,758
£251 per night
includes taxes & fees
Image gallery for Upscale Downtown Lexington Penthouse

1010 out of 10 rating
Exceptional
(6 reviews)
Upscale Downtown Lexington Penthouse
Lexington, KY
28% off
Price is £3,426
£3,426
£489 per night
includes taxes & fees
Image gallery for Luxurious 3 BR Distillery District Townhouse - Eight Belles

1010 out of 10 rating
Exceptional
(11 reviews)
Luxurious 3 BR Distillery District Townhouse - Eight Belles
Lexington, KY
7% off
Price is £2,761
£2,761
£394 per night
includes taxes & fees
Image gallery for Lafferty House-Walk to UK, Woodland Pk, Dn Town, near Bourbon Trail, Horse Farms

1010 out of 10 rating
Exceptional
(46 reviews)
Lafferty House-Walk to UK, Woodland Pk, Dn Town, near Bourbon Trail, Horse Farms
Lexington, KY
24% off
Price is £1,330
£1,330
£190 per night
includes taxes & fees
Image gallery for THE GARDEN VAULT - Culture-Filled Downtown Loft-Style Property, A Must See!

9.29.2 out of 10 rating
Wonderful
(16 reviews)
THE GARDEN VAULT - Culture-Filled Downtown Loft-Style Property, A Must See!
Lexington, KY
15% off
Price is £2,133
£2,133
£305 per night
includes taxes & fees
Image gallery for Private One Bedroom Apartment in Downtown Lexington near Rupp Arena

1010 out of 10 rating
Exceptional
(130 reviews)
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena
Lexington, KY
7% off
Price is £773
£773
£110 per night
includes taxes & fees
Image gallery for Large Two Bedroom Apartment in Downtown Lexington near Rupp Arena

1010 out of 10 rating
Exceptional
(31 reviews)
Large Two Bedroom Apartment in Downtown Lexington near Rupp Arena
Lexington, KY
7% off
Price is £1,114
£1,114
£159 per night
includes taxes & fees
Image gallery for "King's Quarters" Modern Urban Stay - Downtown LEX

1010 out of 10 rating
Exceptional
(17 reviews)
"King's Quarters" Modern Urban Stay - Downtown LEX
Lexington, KY
7% off
Price is £2,329
£2,329
£333 per night
includes taxes & fees
Image gallery for A Renovated 3 Bedroom, 2.5 Bath Townhouse In Downtown Lexington.

9.09.0 out of 10 rating
Wonderful
(116 reviews)
A Renovated 3 Bedroom, 2.5 Bath Townhouse In Downtown Lexington.
Lexington, KY
11% off
Price is £1,144
£1,144
£163 per night
includes taxes & fees
Image gallery for Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena

9.89.8 out of 10 rating
Exceptional
(90 reviews)
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena
Lexington, KY
7% off
Price is £864
£864
£123 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Historic South Hill
Bourbon Hous - 7 Bdrms, Bar, Billiards, Downtown Lexington
Sleeps 14 · 7 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Upscale Downtown Lexington Penthouse
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
THE GARDEN VAULT - Culture-Filled Downtown Loft-Style Property, A Must See!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
16 reviews(16 reviews)
Location, Location, Location
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
46 reviews(46 reviews)
This apartment is a 3 bedroom(s), 1 bathrooms, located in Lexington, KY.
Sleeps 6 · 3 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
This house is a 3 bedroom(s), 2.5 bathrooms, located in Lexington, KY.
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Top rated rentals - Historic South Hill
Fantastic property and awesome welcome
1010 out of 10
Exceptionalexceptional
132 reviews(132 reviews)
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental accommodation in Historic South Hill?
The most in-demand types of holiday rentals in Historic South Hill are houses. Ready for more choices? Vrbo has plenty of options to match our guests’ unique requirements, so you’ll see holiday homes in all sizes and shapes. The ideal fit is ready and waiting for you — get yours today.
How much does it cost to rent a holiday rental in Historic South Hill?
The average price for a holiday rental in Historic South Hill can vary depending on factors like property type, season and length of stay. Whether you’re looking for a sprawling villa with a pool or a cosy cottage just for the two of you, just add your dates of travel to see stays that offer great value.
How much does it cost to rent a beach house in Historic South Hill?
When you travel and the size and style of the property will influence the cost of your beachside escape. Type in your Historic South Hill travel dates to view your options on Vrbo. Can’t live without a hot tub? Use the filters to choose the features and amenities you need.
Are there pet-friendly holiday rentals in Historic South Hill?
With 11 holiday rentals that welcome pets, your furry best friend can join in on your Historic South Hill break. Use the filter tool to browse our pet-friendly holiday rentals and find a stay that’s pawfect on Vrbo.
What are popular rental amenities in Historic South Hill?
When it comes to rental amenities that guests prefer in Historic South Hill, a chef, a barbecue grill and a firepit rank highest. With Vrbo holiday rentals, there are choices to suit your taste and style, whether you’re travelling with relatives, friends or even pets.
Are there large group holiday rentals in Historic South Hill?
With nine Historic South Hill holiday homes that can accommodate a group of five or more people, you can bring a few extra buddies or family members along. Whether you’re planning an informal gathering or a celebratory event, we’ll help you book a comfortable space for the occasion.
Are there holiday rentals in Historic South Hill that welcome kids?
With 11 family-friendly holiday homes to pick from in Historic South Hill, now is the perfect time to introduce your little ones to the magic of travel. Simply check our “Properties good for families” filter to find stays packed with amenities ideal for travelling families, such as extra bedrooms, outdoor spaces, bunk beds and entertainment units.
What are the top attractions for families in Historic South Hill?
Keep the kids amused at these fantastic family-friendly attractions in Historic South Hill:
- Explorium
- Lexington History Centre
- Kentucky Aviation Museum
Can I find two-bedroom holiday rentals in Historic South Hill?
Historic South Hill has five two-bedroom holiday rentals for you to pick from. Find a holiday home with all the privacy and space you want at a fantastic price on Vrbo.
Are there holiday rentals with WiFi in Historic South Hill?
Historic South Hill has three holiday rentals with WiFi, so you can stay connected while you’re travelling. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movies with the family to checking emails, these Vrbo homes will keep you online.
How can I find holiday rentals with air conditioning in Historic South Hill?
Pick your travel dates and then use the filters to look for holiday rentals with ac in Historic South Hill on Vrbo. With 10 air-conditioned properties on offer here, you can look forward to a cool and comfortable break.
How old do you have to be to rent a holiday rental in Historic South Hill?
We recommend checking with the Historic South Hill holiday rental you’re considering on Vrbo as the minimum age differs. However, typically it’s 16, 18 or 21.
How long can I rent a holiday rental in Historic South Hill for?
The length of time you can rent a holiday rental in Historic South Hill differs according to the property. Just enter your desired dates to look at a list of options offering extended stays. With lots of creature comforts such as laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you’re sure to find a perfect place to call your home away from home in Historic South Hill.