Montgomery County Vacations & Trips from $754
Book a Hotel + Flight or Car together to unlock savings
Your Montgomery County Vacation
Embark on your next adventure with a Montgomery County vacation package, and leave knowing all the details are organized. Plus with the ability to tailor your getaway, you know it'll be one to remember. Start your trip to Montgomery County with a visit to Mount Sterling, one of the leading cities here. Start packing your bags, because your Montgomery County vacation is just a few clicks away with Expedia.
Top destinations in Montgomery County
Mount Sterling
The Latest Montgomery County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Hotel Lexington
$1,735
per person
Oct 23 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lexington (LEX)
8.8/10 Excellent! (1,002 reviews)
Clean and comfortable! Very well maintained.
Reviewed on Aug 15, 2026
21c Museum Hotel Lexington
Downtown Lexington
$1,207
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Lexington (LEX)
8.8/10 Excellent! (1,000 reviews)
There was issues with the air conditioner.... the room was very warm and the air conditioner turned off in the middle of the night.
Reviewed on Aug 15, 2026
Find the Best Montgomery County Vacation Packages
Montgomery County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Blue Grass Airport (LEX) |
Montgomery County Hotel Deals
Natural Bridge State Resort Park
2135 Natural Bridge Road Slade KY
Fully refundableReserve now, pay when you stay
$106 nightly
$117 total
Aug 20 - Aug 21
Total with taxes and fees
8.6/10 Excellent! (1,999 reviews)
"Such a cool place to stay. I grew up visiting the area, my dad was from there. Very convenient to one of the many trails to visit Natural Bridge. The room was clean, just the right size and a private balcony to enjoy the view. The restaurant has the best food ever, I ate there every night and the ..."
Reviewed on Aug 15, 2026
Dog-friendly Home Rental ~ 5 Mi to Cave Run Lake!
Wellington KY
10/10 Exceptional! (1 review)
"We had an amazing time and the property was very nice. We spent every night out in the hot tub. Highly recommend booking this place!"
Reviewed on Jul 9, 2025
Baymont by Wyndham Winchester
960 Interstate Dr Winchester KY
Fully refundableReserve now, pay when you stay
$76 nightly
$83 total
Aug 17 - Aug 18
Total with taxes and fees
7.2/10 Good! (835 reviews)
"Très bien"
Reviewed on Aug 9, 2026
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.
Stay near popular Montgomery County attractions
Mount Sterling Library
Mount Sterling Library is just one of the places to see in Mount Sterling, so why not enjoy the other things to explore during your travels? While in this family-friendly area, you can enjoy the restaurants.
Gateway Regional Arts Center
Enjoy an outing to Gateway Regional Arts Center during your stay in Mount Sterling. While in this family-friendly area, you can enjoy the restaurants.
Old Silo Golf Course
Enjoy a round of golf in Mount Sterling at Old Silo Golf Course. While in this family-friendly area, you can enjoy the restaurants.
Explore a world of travel with Expedia
Other vacations you might like
- Top cities in Montgomery County
- Vacations and getaways similar to Montgomery County
- Best vacation destinations by month
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.