North Upper Street Vacation Packages

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Top Holiday Package Deals in North Upper Street

Price found within the past 48 hours. Click for updated prices.
GLō Best Western Lexington

GLō Best Western Lexington

3 out of 5
Price was CA $1,424, price is now CA $1,359 per person
CA $1,359
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Kitchener (YKF) to Lexington (LEX)
9.4/10 Exceptional! (2,270 reviews)
Clean room, excellent breakfast managed so well.

Reviewed on Feb 20, 2026

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was CA $1,566, price is now CA $1,414 per person
CA $1,414
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Kitchener (YKF) to Lexington (LEX)
8.8/10 Excellent! (1,002 reviews)
Clean room. Great staff. Restaurant was delicious.

Reviewed on Feb 15, 2026

Residence Inn Lexington Keeneland/Airport

Residence Inn Lexington Keeneland/Airport

3 out of 5
Beaumont Residential
Price was CA $1,649, price is now CA $1,547 per person
CA $1,547
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Kitchener (YKF) to Lexington (LEX)
9/10 Wonderful! (560 reviews)
It was great everything was so clean and the staff was awesome and the lady who makes the breakfast omg she did amazing

Reviewed on Feb 15, 2026

Courtyard Lexington Keeneland/Airport

Courtyard Lexington Keeneland/Airport

3 out of 5
Beaumont Residential
Price was CA $1,618, price is now CA $1,521 per person
CA $1,521
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Kitchener (YKF) to Lexington (LEX)
8.8/10 Excellent! (796 reviews)
The staff is very friendly. Rooms are very clean. Located in safe, convenient area.

Reviewed on Nov 11, 2025

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

3 out of 5
Price was CA $1,473, price is now CA $1,402 per person
CA $1,402
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Kitchener (YKF) to Lexington (LEX)
8.6/10 Excellent! (1,002 reviews)
Nice room. Very courteous staff

Reviewed on Feb 21, 2026

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
4th of July festival

Downtown Lexington

2 out of top 10 points of interest in this area
4/5(1 area review)

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

The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Mar 22 to Mar 23
CA $232
CA $293 total
Mar 22 - Mar 23
includes taxes & fees
9.6/10 Exceptional! (1,169 reviews)
The room was clean and cozy. Very enjoyable amenities and location.

Reviewed on Feb 22, 2026

The Manchester
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 CA $162 per night from Mar 15 to Mar 16
CA $162
CA $188 total
Mar 15 - Mar 16
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
Extremely nice staff and hotel was clean. They offered a few gluten free options in the restaurant. However I have to take some stars off because in our room facing the lobby/restaurant, you could hear people down there talking and laughing in the night. There were two bigs groups staying there that ...

Reviewed on Feb 22, 2026

DoubleTree Suites by Hilton Hotel Lexington
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street Lexington KY
The price is CA $205 per night from Mar 8 to Mar 9
CA $205
CA $238 total
Mar 8 - Mar 9
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
Yes everything was good!

Reviewed on Feb 20, 2026

Hilton Lexington/Downtown
See all 850 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.
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All Inclusive Vacations
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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 CA $1,359. 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.

Discover the most popular places to visit in North Upper Street

Panorama of an autumn, colorful lawn surrounded by buildings in downtown Lexington, Kentucky

University of Kentucky

4.5/5(7 reviews)

Take a campus tour or just explore the area around University of Kentucky, a top university 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

4.5/5(12 reviews)

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
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The Kentucky Castle

Enjoy a trip to The Kentucky Castle and popular activities like horseback riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area.

The Kentucky Castle

Things to do

Unique Horse Farm Tours with Insider Access to Private Farms

Unique Horse Farm Tours with Insider Access to Private Farms

CA $80
per adult
90% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
Lexington: Downtown Walking Food & History Tour

Lexington: Downtown Walking Food & History Tour

CA $135
per adult
Lexington: Downtown Walking Food & History Tour
Bites of the Bluegrass Cocktails & Bites Tour

Bites of the Bluegrass Cocktails & Bites Tour

CA $142
per adult
Bites of the Bluegrass Cocktails & Bites 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.