North Upper Street Holidays

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Your North Upper Street Holiday

Our North Upper Street holiday packages are a simple and practical way to organise and reserve your next break. Uncover the magic of this unique neighbourhood without the bother of organising it all yourself. When it's time to get out and explore, you'll find loads of popular attractions nearby including University of Kentucky, Kroger Field and Rupp Arena. Visit one, two or more during your trip to North Upper Street. Don't just imagine it — do it! Reserve your ideal North Upper Street holiday with Expedia and get to where you're going your way.

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
4th of July festival

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 AU$300 per night from 15 Feb to 16 Feb
AU$300
15 Feb - 16 Feb
includes taxes & fees
9.4/10 Exceptional! (1,140 reviews)
Great place to stay, eat and drink.

Reviewed on 20 Jan 2026

The Manchester
Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

2.5 out of 5
2381 Buena Vista Rd Lexington KY
Fully refundableReserve now, pay when you stay
The price is AU$101 per night from 15 Feb to 16 Feb
AU$101
15 Feb - 16 Feb
includes taxes & fees
8.6/10 Excellent! (336 reviews)
For a new property I had hoped for a better built hotel. The walls are paper thin and we heard people in every room around us. Breakfast was subpar. The staff was good.

Reviewed on 29 Jan 2026

Spark by Hilton Lexington Hamburg
Hyatt Regency Lexington

Hyatt Regency Lexington

3.5 out of 5
401 W High St Lexington KY
The price is AU$240 per night from 15 Feb to 16 Feb
AU$240
15 Feb - 16 Feb
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Overall, it's good. The room is clean. The breakfast is delicious, but you have to order it yourself, which is relatively expensive.

Reviewed on 28 Jan 2026

Hyatt Regency Lexington
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.
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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.
Can I choose my airline with a North Upper Street Expedia holiday package?
You sure can. Expedia has access to more than 550 airline partners globally, so fly with the carrier that best fits your budget and travelling style.
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

The bottling line for the special single barrel Blantons Bourbon.

Buffalo Trace Distillery

You can take time to visit Buffalo Trace Distillery during your travels to Frankfort. You can seek out the hiking trails while in the area.

Buffalo Trace Distillery
Aerial photograph of the Lexington, Kentucky skyline at night with the city alite.

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
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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

Activities

Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

AU$88
per adult
90% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

AU$148
per adult
Lexington: Downtown Walking Food & History Tour
Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

AU$15
per adult
80% of travellers recommend
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.