North Upper Street Vacations from $309

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Your North Upper Street Vacation

Our North Upper Street vacation packages are a simple and practical way to organize and reserve your next break. Uncover the magic of this unique neighborhood without the bother of organizing 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 vacation with Expedia and get to where you're going your way.

The Latest North Upper Street Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Capital Plaza Hotel

Capital Plaza Hotel

3 out of 5
Price was $361, price is now $309 per person
$309
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip flight included
Washington (WAS) to Lexington (LEX)
8.2/10 Very Good! (1,001 reviews)
Front desk staff was the best! The bed was not good. Linens not the best. Loud traffic outside. Older hotel but clean and it was fine for one night.

Reviewed on Sep 5, 2025

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Save 100% on your flight
Price was $1,978, price is now $1,510 per person
$1,510
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip flight included
New York (LGA) to Lexington (LEX)
8.8/10 Excellent! (1,008 reviews)
Amazing staff and beautiful hotel

Reviewed on Aug 29, 2025

Hampton Inn Richmond

Hampton Inn Richmond

2.5 out of 5
Price was $797, price is now $680 per person
$680
per person
Oct 16 - Oct 21
found 23 hours ago
Roundtrip non-stop flight included
New York (LGA) to Lexington (LEX)
9.2/10 Wonderful! (1,008 reviews)
The hotel had outdoor renovations taking place, it didn't disrupt anytime we had to do.

Reviewed on Sep 2, 2025

Courtyard Lexington Keeneland/Airport

Courtyard Lexington Keeneland/Airport

3 out of 5
Beaumont Residential
Price was $449, price is now $396 per person
$396
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip flight included
Washington (WAS) to Lexington (LEX)
8.8/10 Excellent! (777 reviews)
Everything first class. A very enjoyable stay, and personable help on the desk to get us settled in easily. Thanks for everything!

Reviewed on Sep 4, 2025

Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg

3 out of 5
Price was $404, price is now $359 per person
$359
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip flight included
Washington (WAS) to Lexington (LEX)
9.2/10 Wonderful! (965 reviews)
Room was very clean..Staff was nice…would definitely stay again if passing through!!!

Reviewed on Sep 4, 2025

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 showing tranquil scenes and farmland

Downtown Lexington

1 out of top 10 points of interest in this area
4.5/5(27 area reviews)

While visiting Downtown Lexington, you might make a stop by sights like Lexington Opera House and Rupp Arena.

Find hotels in Downtown Lexington

North Upper Street Hotel Deals

Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street, Lexington, KY
$166 nightly
The price is $193 total per night from Sep 14 to Sep 15
$193 total
Sep 14 - Sep 15
Total with taxes and fees
Hilton Lexington/Downtown
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
$111 nightly
The price is $129 total per night from Sep 22 to Sep 23
$129 total
Sep 22 - Sep 23
Total with taxes and fees
DoubleTree Suites by Hilton Hotel Lexington
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $82 total per night from Sep 21 to Sep 22
$82 total
Sep 21 - Sep 22
Total with taxes and fees
GuestHouse Lexington
See all 837 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in North Upper Street

Kentucky Horse Park showing land animals

Kentucky Horse Park

Experience the exciting worlds of horses and horseracing at this equine theme park with multiple museums in the middle of Kentucky’s horse country.

Kentucky Horse Park
In a hores eye #2

University of Kentucky

Explore the campus of University of Kentucky, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.

University of Kentucky
It's beginning to look a lot like Christmas.

Fayette Mall

You can find the perfect gifts to bring home at Fayette Mall during your stay in Lexington. Discover the area's acclaimed theater scene, or seek out its horseback riding.

Fayette Mall

Things to do

Experience Rebecca Ruth Chocolate Tour & Museum!

Experience Rebecca Ruth Chocolate Tour & Museum!

$10
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

$99
per adult
Lexington: Downtown Walking Food & History Tour
Distillery District Food & History Tour in Lexington

Distillery District Food & History Tour in Lexington

$99
per adult
Distillery District Food & History Tour in Lexington
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.