North Upper Street Vacations
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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
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.
Northside District
If you're spending some time in Northside District, Lexington Opera House and West Sixth Brewing are top sights worth seeing.
Liberty Area
If you're spending some time in Liberty Area, Hamburg Place and Hamburg Pavilion are top sights worth seeing.
Picadome
When in Picadome, you can plan a visit to Kroger Field and Red Mile Racetrack, some noteworthy sights in the nearby area.
Historic South Hill
While Historic South Hill might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lexington Memorial Coliseum and Rupp Arena.
North Upper Street Hotel Deals
Holiday Inn Express Lexington - Horse Park Area by IHG
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
NT$3,164
NT$3,673 total
Sep 29 - Sep 30
includes taxes & fees
9.4/10 Exceptional! (2,246 reviews)
"The hotel was clean and quiet. The adaptive bathroom was outstanding. The hotel was accessible an all points. The morning breakfast wad good although lifting the lids on the food was not as easy from a wheelchair but not real different from other hotels. For people with adaptive needs. I would recommend ..."
Reviewed on 2026/9/10
Hyatt Regency Lexington
401 W High St Lexington KY
Fully refundableReserve now, pay when you stay
NT$4,272
NT$4,958 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"Staff was absolutely fantastic"
Reviewed on 2026/9/12
21c Museum Hotel Lexington
167 West Main Street Lexington KY
Fully refundableReserve now, pay when you stay
NT$4,333
NT$5,188 total
Sep 27 - Sep 28
includes taxes & fees
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 vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in North Upper Street from just . And the more you bundle, the more dollars you save. The vacation 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 vacation 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 vacation 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 favorites.
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 vacation?
Travelers 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 vacation 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 traveling style.
If I'm not able to travel, can I cancel my North Upper Street vacation 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.
Stay near popular North Upper Street attractions
Transylvania University
8.6/10 (48 reviews)
Enjoy the collegiate vibe when you visit Transylvania University, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.