North Upper Street Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by RVOutlawz

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 farmland and tranquil scenes

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

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 3.242.526 ₫ per night from 23 Dec to 24 Dec
3.242.526 ₫
3.763.601 ₫ total
23 Dec - 24 Dec
includes taxes & fees
8.4/10 Very Good! (1,012 reviews)
Room was excessively hot, could not sleep at all. A tremendous disappointment

Reviewed on 8 Dec 2025

Hilton Lexington/Downtown
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road Lexington KY
Fully refundableReserve now, pay when you stay
The price is 1.783.126 ₫ per night from 15 Dec to 16 Dec
1.783.126 ₫
2.069.673 ₫ total
15 Dec - 16 Dec
includes taxes & fees
8.2/10 Very Good! (1,492 reviews)
A quiet clean place as always

Reviewed on 8 Dec 2025

GuestHouse Lexington
The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is 4.035.758 ₫ per night from 21 Dec to 22 Dec
4.035.758 ₫
5.143.265 ₫ total
21 Dec - 22 Dec
includes taxes & fees
9.4/10 Exceptional! (1,076 reviews)
Beautifully appointed boutique hotel.

Reviewed on 8 Dec 2025

The Manchester
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 1null000null000 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

Fayette Mall

Fayette Mall

3/5(2 reviews)

You can do some window-shopping at Fayette Mall during your trip to Lexington. Discover the area's acclaimed theatre scene or seek out its horse riding.

Fayette Mall
The Kentucky Castle

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
Eastern Kentucky University

Eastern Kentucky University

4/5(1 review)

Enjoy the student vibe when you visit Eastern Kentucky University during your travels in Richmond. While in this family-friendly area, you can savour the top-notch restaurants.

Eastern Kentucky University