North Upper Street Holidays

Photo by RVOutlawz

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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
Lexington featuring tranquil scenes and farmland

Downtown Lexington

1 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

Top hotels in North Upper Street

The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is S$219 per night from 26 Jan to 27 Jan
S$219
26 Jan - 27 Jan, 2026
includes taxes & fees
9.4/10 Exceptional! (1,090 reviews)
Such a wonderful hotel and love the lobby for drinks and bar food

Reviewed on 21 Dec, 2025

The Manchester
Motel 6 Lexington, KY - Airport

Motel 6 Lexington, KY - Airport

2 out of 5
750 Newtown Court Lexington KY
Fully refundable
The price is S$76 per night from 10 Jan to 11 Jan
S$76
10 Jan - 11 Jan, 2026
includes taxes & fees
5.8/10 (1,007 reviews)
Welcoming

Reviewed on 19 Dec, 2025

Motel 6 Lexington, KY - Airport
Candlewood Suites Lexington Medical District by IHG

Candlewood Suites Lexington Medical District by IHG

2.5 out of 5
501 Waller Avenue Lexington KY
Fully refundable
The price is S$116 per night from 1 Jan to 2 Jan
S$116
1 Jan - 2 Jan, 2026
includes taxes & fees
9.2/10 Wonderful! (813 reviews)
Everything was amazing, everyone was super nice, the room was very clean and comfy close to the hospital because we had to be there at 5:30am… it was also my birthday so… I was so happy with my stay!

Reviewed on 22 Dec, 2025

Candlewood Suites Lexington Medical District by IHG
See all 846 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.

Popular places to visit

Keeneland Racing Course

Enjoy a trip to Keeneland Racing Course and popular activities such as horse riding in Lexington. You can attend a sporting event while in the area.

Keeneland Racing Course

Rupp Arena

Catch an event at Rupp Arena and enjoy other activities in Lexington such as horse riding.Attend a sporting event or simply enjoy the lively bars while you're in the area.

Rupp Arena

Things to do

Picture 1 for Activity Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass

S$58
per adult
98% of travellers recommend
Lexington: Thoroughbred Horse Farm Tour and Scenic Bluegrass
Makers Mark, Four Roses or Woodford Reserve or Bulleit or Others

Groups: Makers Mark OR Buffalo Trace OR Woodford or Others

S$233
per adult
Groups: Makers Mark OR Buffalo Trace OR Woodford or Others
Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

S$69
per adult
90% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.