North Upper Street Vacations from $781

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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.
21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $926, price is now $781 per person
$781
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Lexington (LEX)
8.8/10 Excellent! (1,003 reviews)
Amazing staff and beautiful hotel

Reviewed on Aug 29, 2025

Staybridge Suites Lexington S Medical Ctr Area by IHG

Staybridge Suites Lexington S Medical Ctr Area by IHG

3 out of 5
Price was $1,519, price is now $1,283 per person
$1,283
per person
Oct 16 - Oct 20
found 7 hours ago
Roundtrip non-stop flight included
New York (JFK) to Lexington (LEX)
9.8/10 Exceptional! (423 reviews)
Everything we needed! Beds are great, property clean and welcoming.

Reviewed on Sep 3, 2025

Home2 Suites by Hilton Lexington University / Medical Center

Home2 Suites by Hilton Lexington University / Medical Center

3 out of 5
Zandale
Price was $1,220, price is now $1,036 per person
$1,036
per person
Oct 23 - Oct 27
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Lexington (LEX)
8.8/10 Excellent! (990 reviews)
Angel was very helpful and friendly.

Reviewed on Aug 31, 2025

The Sire Hotel Lexington, Tapestry Collection by Hilton

The Sire Hotel Lexington, Tapestry Collection by Hilton

3.5 out of 5
Downtown Lexington
Price was $940, price is now $815 per person
$815
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Lexington (LEX)
9.4/10 Exceptional! (820 reviews)
Like: The neighborhood and close dining. Breakfast was nice. Staff were awesome! Thank you. A little bit let down by the "spa shower".

Reviewed on Jul 29, 2025

Homewood Suites by Hilton Lexington Fayette Mall

Homewood Suites by Hilton Lexington Fayette Mall

3 out of 5
Price was $1,122, price is now $978 per person
$978
per person
Oct 23 - Oct 27
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Lexington (LEX)
9/10 Wonderful! (743 reviews)
Having been married for 50 years and traveling a lot, we have to say this is the best hotel experience we have ever had. From comfort to cleanliness, everything was great! Our suite was spacious and felt like home complete with everything we needed! And the food was amazing! Not your standard hotel breakfast…theirs is awesome! We loved it so much we extended our stay! We are hooked on Hilton Homewood Suites and will always book with them as we travel!

Reviewed on Aug 30, 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

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
$114 nightly
The price is $132 total per night from Sep 14 to Sep 15
$132 total
Sep 14 - Sep 15
Total with taxes and fees
DoubleTree Suites by Hilton Hotel Lexington
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street, Lexington, KY
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $188 total per night from Sep 7 to Sep 8
$188 total
Sep 7 - Sep 8
Total with taxes and fees
Hilton Lexington/Downtown
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $77 total per night from Sep 14 to Sep 15
$77 total
Sep 14 - Sep 15
Total with taxes and fees
GuestHouse Lexington
See all 830 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.