Photo by RVOutlawz
North Upper Street holiday homes
We found 128 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in North Upper Street that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll have the amenities that you expect and more, which might include Wi-Fi and a pool. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - North Upper Street
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 NZ$17,324
NZ$17,324
NZ$2,475 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 NZ$18,270
NZ$18,270
NZ$2,610 per night
includes taxes & fees
Image gallery for Kentucky Dream! 4BR, 3BA, 2Car-G/Covered Backyard Stage, 1-Mile from Rupp!

1010 out of 10 rating
Exceptional
(8 reviews)
Kentucky Dream! 4BR, 3BA, 2Car-G/Covered Backyard Stage, 1-Mile from Rupp!
Lexington, KY
7% off
Price is NZ$9,986
NZ$9,986
NZ$1,427 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
8% off
Price is NZ$10,501
NZ$10,501
NZ$1,500 per night
includes taxes & fees
Image gallery for Welcome to “The Spot” - North Limestone/Downtown!

1010 out of 10 rating
Exceptional
(29 reviews)
Welcome to “The Spot” - North Limestone/Downtown!
Lexington, KY
10% off
Price is NZ$3,619
NZ$3,619
NZ$517 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 NZ$7,463
NZ$7,463
NZ$1,066 per night
includes taxes & fees
Image gallery for Luxurious 3 BR Distillery District Townhouse - Eight Belles

1010 out of 10 rating
Exceptional
(10 reviews)
Luxurious 3 BR Distillery District Townhouse - Eight Belles
Lexington, KY
7% off
Price is NZ$6,005
NZ$6,005
NZ$858 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 NZ$4,697
NZ$4,697
NZ$671 per night
includes taxes & fees
Image gallery for Modern Comfort & Lexington Charm – Near UK & Keeneland!

1010 out of 10 rating
Exceptional
(19 reviews)
Modern Comfort & Lexington Charm – Near UK & Keeneland!
Lexington, KY
11% off
Price is NZ$2,626
NZ$2,626
NZ$375 per night
includes taxes & fees
Image gallery for Private One Bedroom Apartment in Downtown Lexington near Rupp Arena

1010 out of 10 rating
Exceptional
(129 reviews)
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena
Lexington, KY
7% off
Price is NZ$1,705
NZ$1,705
NZ$244 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 NZ$2,441
NZ$2,441
NZ$349 per night
includes taxes & fees
Image gallery for DOWNTOWN, Rupp Arena just 5 min away. 2 bedr/1 Bath cozy home.

9.29.2 out of 10 rating
Wonderful
(9 reviews)
DOWNTOWN, Rupp Arena just 5 min away. 2 bedr/1 Bath cozy home.
Lexington, KY
7% off
Price is NZ$1,452
NZ$1,452
NZ$207 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 NZ$5,435
NZ$5,435
NZ$776 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 NZ$2,505
NZ$2,505
NZ$358 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 NZ$1,902
NZ$1,902
NZ$272 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - North Upper Street
Updated Home | Downtown | Luxe Beds | Ping Pong
Sleeps 12 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
Hidden Gem Charming 2-bedroom apartment in delightful Lexington
Sleeps 4 · 2 bedrooms · 1 bathroom
8.08.0 out of 10
Very goodvery good
1 review(1 review)
Modern Comfort & Lexington Charm – Near UK & Keeneland!
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
Location, Location, Location
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
Witches Cottage - Downtown LEX
Sleeps 2 · 1 bathroom
1010 out of 10
Exceptionalexceptional
Luxe Home Downtown - Sleeps 6. Off-street parking
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
17 reviews(17 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, laundry, 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 home accommodation in North Upper Street?
Houses are the most popular type of holiday home in North Upper Street, according to our data. Even if you have a different idea about what you want, Bookabach has holiday homes in loads of shapes and sizes. Filter our options to find your perfect fit.
How much does it cost to rent a holiday home in North Upper Street?
The average price for a holiday home in North Upper Street is based on several factors, including length of stay, season and property type. Whether you prefer a villa with space for extended family or an apartment ideal for just you and the kids, just add your dates of travel to discover stays with unbeatable value.
How much does it cost to rent a beach house in North Upper Street?
The average price for a holiday home near the beach in North Upper Street depends on when you’ll be there and the style and size of property you want. Find prices quickly and easily on Bookabach by entering your travel dates and destination. Then use our filter tool to choose the number of bedrooms and amenities that you prefer, such as WiFi, air conditioning and a pool.
Are there pet-friendly holiday homes in North Upper Street?
You’re in luck! There are. You’ll have a choice of nine holiday homes that cater to pets in North Upper Street. Lots of our pet-friendly holiday homes even have a backyard for your furry pal to have fun in, complimentary treats, special dog beds and proximity to parks. Apply the “Pets allowed” filter to find your pawfect place on Bookabach.
What are popular home amenities in North Upper Street?
A barbecue grill, a fireplace and nearby museums are rated the most popular home amenities in North Upper Street. Whether you’re taking to the road on your own, with your significant other or a group of family members, Bookabach will help you find a holiday home that suits your tastes with all the extras you’re looking for.
Are there large group holiday homes in North Upper Street?
There are five holiday homes in North Upper Street that can sleep five or more people. From family getaways to special occasions like birthday parties, these stays have enough space to hang out with your favourite people.
Are there holiday homes in North Upper Street that welcome kids?
With eight family-friendly holiday homes available in North Upper Street, now is a great time to introduce your little ones to the magic of travel. Click on our “Properties good for families” filter to browse stays that feature amenities perfect for holidaying families, like multiple bedrooms, swimming pools, bunk beds and entertainment areas.
What are the top attractions for families in North Upper Street?
There are plenty of amazing things to do and see with the family in North Upper Street, such as:
- Explorium
- Lexington History Centre
- Kentucky Aviation Museum
Are there one-bedroom holiday homes in North Upper Street?
Yes, North Upper Street has two one-bedroom homes on offer. Typically situated in prime spots thanks to their smaller size, a one-bedroom holiday property is perfect if you’re travelling with a buddy or your partner. And with plenty of home comforts like full kitchens and more privacy than a standard hotel, you’ll be able to relax while sightseeing around this exciting destination.
Can I find two-bedroom holiday homes in North Upper Street?
Gather your besties and enjoy a relaxing escape in one of the two two-bedroom holiday homes North Upper Street has to offer.
Are there holiday homes with WiFi in North Upper Street?
Whether you want to stay in touch with the news, send a few emails or post a pic to social media, there are two holiday homes with WiFi in North Upper Street. Check the “WiFi” box when searching on Bookabach and stay connected on your getaway.
How can I find holiday homes with air conditioning in North Upper Street?
You can pick from eight Bookabach holiday homes with air conditioning in North Upper Street giving you that cool, cool breeze and extra level of comfort. Just enter your dates of travel and then use our handy filters to find stays with air conditioning.
How old do you have to be to rent a holiday home in North Upper Street?
We advise checking with the North Upper Street holiday property you want on Bookabach as the minimum age varies. However, typically it’s 16, 18 or 21.
How long can I rent a holiday home in North Upper Street for?
The length of time you can book a holiday home in North Upper Street differs according to the property. Just enter your preferred travel dates to look at a list of options offering extended stays. With loads of creature comforts such as kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you’re sure to discover somewhere perfect to call your home away from home in North Upper Street.