North Upper Street Holidays

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Our guide on where to stay in North Upper Street

Find the best North Upper Street areas and neighborhoods for the activities you enjoy most. Learn more about North Upper Street
Downtown Lexington

Downtown Lexington

2 out of top 10 points of interest in this area

While visiting Downtown Lexington, you might make a stop by sights like Lexington Opera House and Rupp Arena.

Find hotels in Downtown Lexington

Our pick of the best North Upper Street Hotel Deals

The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is NZ$386 per night from 25 May to 26 May
NZ$386
25 May - 26 May
includes taxes & fees
9.6/10 Exceptional! (1,279 reviews)
Exceeded expectations

Reviewed on 11 May 2026

The Manchester
Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
The price is NZ$202 per night from 17 May to 18 May
NZ$202
17 May - 18 May
includes taxes & fees
9.4/10 Exceptional! (2,187 reviews)
Pleased with rooms. Decent breakfast. Friendly staff.

Reviewed on 11 May 2026

Holiday Inn Express Lexington Horse Park Area by IHG
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street Lexington KY
Fully refundableReserve now, pay when you stay
The price is NZ$278 per night from 20 May to 21 May
NZ$278
20 May - 21 May
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
Room was clean and comfy and had everything you needed.

Reviewed on 11 May 2026

Hilton Lexington/Downtown
See all 856 properties in North Upper Street
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.

Frequently asked questions

How much does a North Upper Street holiday package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in North Upper Street from just . And the more you bundle, the more dollars you save. The holiday of your dreams has never been so affordable.
How do I get a cheap travel package to North Upper Street?
Combine your flight and hotel bookings, add extras such as tours, and save with a North Upper Street holiday package. You won't just score big discounts on your getaway — you'll have lots of choice too. When you book through Expedia, you can select from more than 550 airlines and 1 000 000 properties around the globe. Your dream holiday starts right here, right now!
Where should I stay in North Upper Street?
Take the hassle out of sightseeing by staying right around the corner from North Upper Street's big attractions. University of Kentucky and Keeneland Racing Course are two visitor favourites.
What are the top hotels in North Upper Street?
If it's comfort and convenience you're looking for, you can't go past Cute Two - Story Downtown Shotgun Home. Spend your nights relaxing here and your days wandering around North Upper Street's most well-known attractions.
How far in advance should I book my North Upper Street holiday?
Travellers can normally look up international fares on Expedia within 12 months of the departure date. Booking last minute? With a bit of luck, it's still possible to nab an affordable ticket just weeks before your flight.
What does an Expedia North Upper Street travel package include?
Choose from any combination of rental cars, flights and hotels. Once you've made your booking, you can also add on activities and experiences. Want to pick your fare class? That's easy to do too. The choice is all yours when it comes to crafting your ideal North Upper Street escape.
What should I know before booking a North Upper Street travel package?
We already have low prices. However, you'll score even more savings if you book your flights, hotels and car rentals together. With an Expedia package, you'll always get transparent pricing and loads of choice.
If I'm not able to travel, can I cancel my North Upper Street holiday package?
Yes, you can cancel your North Upper Street booking if your plans have been upended. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. You may be able to cancel or change your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

Discover the most popular places to visit in North Upper Street

Kentucky Horse Park

Kentucky Horse Park

Enjoy a trip to Kentucky Horse Park and popular activities such as horse riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Kentucky Horse Park
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The Kentucky Castle

Enjoy a trip to The Kentucky Castle and popular activities such as horse riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.

The Kentucky Castle

Red Mile Racetrack

Enjoy a trip to Red Mile Racetrack and popular activities such as horse riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Red Mile Racetrack

Activities

Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

NZ$100
per adult
90% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

NZ$17
per adult
80% of travellers recommend
Experience Rebecca Ruth Chocolate Tour & Museum!
Experience Rebecca Ruth Chocolate Tour & Museum

Experience Rebecca Ruth Chocolate Tour & Museum

NZ$17
per adult
Experience Rebecca Ruth Chocolate Tour & Museum
See all activities in Lexington
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.