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
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

Our pick of the best North Upper Street Hotel Deals

DoubleTree Suites by Hilton Hotel Lexington
DoubleTree Suites by Hilton Hotel Lexington
4 out of 5
2601 Richmond Rd, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is NZ$234 per night from 6 July to 7 July
NZ$234
6 July - 7 July
includes taxes & fees
8.6/10 Excellent! (1,012 reviews)
"The outdoor pool was too close to the dumpster. The room is nice but the AC unit is way loud. Parking was plenty and easy. Most guests were supper friendly and courteous. Some guests on the same floor we stayed on Friday were inconsiderate and constantly entering and leaving and knocking and slamming ..."

Reviewed on 24 Jun. 2025

DoubleTree Suites by Hilton Hotel Lexington
Elwood Hotel & Suites
Elwood Hotel & Suites
4 out of 5
444 Parkway Drive, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is NZ$188 per night from 29 June to 30 June
NZ$188
29 June - 30 June
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Excellent!!"

Reviewed on 25 Jun. 2025

Elwood Hotel & Suites
Fairfield Inn & Suites by Marriott Lexington North
Fairfield Inn & Suites by Marriott Lexington North
3 out of 5
2100 Hackney Pl, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is NZ$161 per night from 20 July to 21 July
NZ$161
20 July - 21 July
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"The staff is nice, but the property is somewhat in need of repair. The pool and the hot tub area particularly needs repair and has some repaired water damage and in need of some repairs to the shower faucet etc. Accommodations within the room are just fine and the location is perfect."

Reviewed on 26 Jun. 2025

Fairfield Inn & Suites by Marriott Lexington North
See all 836 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

Explore Kentucky Horse Park, a favourite green space in Lexington, and also enjoy the area's horse riding. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Kentucky Horse Park
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

The Red Mile Racetrack

Enjoy a trip to The 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.

The Red Mile Racetrack

Activities

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

NZ$50
per traveller
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

NZ$17
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

NZ$165
per adult
Lexington: Downtown Walking Food & History Tour
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.