Historic Uptown Lexington Vacations from $279
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The Latest Historic Uptown Lexington Vacation Packages
Price found within the past 48 hours. Click for updated prices.
O.Henry Hotel
Save 100% on your flight
Price was $962, price is now $675 per person
$675
per person
Feb 21 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
9.8/10 Exceptional! (724 reviews)
Nice place to Stay in Greensboro, NC. I didn’t anticipate the country club warm vibe in a Metropolitan area.
Reviewed on Dec 6, 2025
Historic Uptown Lexington Hotel Deals
Hawthorne Inn and Conference Center
420 High St Winston-Salem NC
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $80 total per night from Dec 14 to Dec 15
$80 total
Dec 14 - Dec 15
Total with taxes and fees
8.2/10 Very Good! (1,015 reviews)
Room was Clean and beds where really comfortable, but this hotel is really old the toilet and bathroom was really small.
Reviewed on Dec 8, 2025
Holiday Inn Express Winston-Salem Medical Center Area by IHG
110 Miller Street Winston-Salem NC
Fully refundable
$89 nightly
The price is $101 total per night from Dec 21 to Dec 22
$101 total
Dec 21 - Dec 22
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
Clean room. Adequate and safe parking.
Reviewed on Dec 3, 2025
The Historic Brookstown Inn, Trademark Collection by Wyndham
200 Brookstown Ave Winston-Salem NC
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $127 total per night from Jan 1 to Jan 2
$127 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.4/10 Exceptional! (1,006 reviews)
This place was fabulous. It was an experience with their wine and cheese hours. Then milk and cookies. And the breakfast was delicious. I highly recommend this hotel. It was well renovated while preserving the historic building.
Reviewed on Dec 6, 2025
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.
Discover the most popular places to visit in Historic Uptown Lexington
Boone's Cave Park
Explore the great outdoors at Boone's Cave Park, a lovely green space in Lexington. While in this family-friendly area, you can savor the wineries and restaurants.
The Candy Factory
Take the family on an outing to The Candy Factory during your trip to Lexington. Savor the area's wineries and restaurants.
Richard Childress Vineyards
4/5(19 reviews)
You can enjoy a tasting or tour at Richard Childress Vineyards during your travels to Lexington. Stroll along this family-friendly area's lakeside, or simply enjoy its wineries.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.