Deals on vacations and trips to Montgomery County

Save when you book Montgomery County, KY package deals

Choose two or more items and save on your trip:

Search vacation packages deals in Montgomery County's top destinations

An aerial view of a town with historic buildings, a central green area, and a parking lot.

Mount Sterling

Vacations
Mount Sterling

Montgomery County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Shaker Village of Pleasant Hill

Shaker Village of Pleasant Hill

3.5 out of 5
Shakertown
Price was $663, price is now $552 per person
$552
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Lexington (LEX)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 6 conference rooms, along with express check-out. A restaurant, a 24-hour front desk, and wedding services are also provided.
21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $909, price is now $750 per person
$750
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Lexington (LEX)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a 24-hour business center, and a snack bar/deli are also offered.
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was $890, price is now $791 per person
$791
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Lexington (LEX)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A lobby fireplace, express check-out, and dry cleaning are also on offer.
Springhill Suites by Marriott Lexington Fritz Farm

Springhill Suites by Marriott Lexington Fritz Farm

3 out of 5
Price was $780, price is now $705 per person
$705
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Lexington (LEX)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was $873, price is now $794 per person
$794
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Lexington (LEX)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Free self parking and a coffee shop are also offered on site.

Top Montgomery County hotels deals

Ramada Limited Mount Sterling

Ramada Limited Mount Sterling

2 out of 5
115 Stone Trace Dr Mount Sterling KY
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $83 total per night
$83 total
Oct 11 - Oct 12
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 out of 5
2135 Natural Bridge Road Slade KY
$116 nightly
The price is $128 total per night
$128 total
Sep 30 - Oct 1
Total with taxes and fees
A restaurant and a bar/lounge are featured at this cabin. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A picnic area is provided and the front desk is staffed around-the-clock.
Black Bear Lodge Motel

Black Bear Lodge Motel

2.5 out of 5
781 Natural Bridge Rd Slade KY
$88 nightly
The price is $97 total per night
$97 total
Sep 30 - Oct 1
Total with taxes and fees
This motel features a coffee shop, barbecue grills, and free self parking. A convenience store and a picnic area are also provided.
TURNING LEAF•Cozy Cabin in the RRG• Couples Retreat

TURNING LEAF•Cozy Cabin in the RRG• Couples Retreat

Pine Ridge KY
Get rates
This cabin includes free WiFi in public areas and barbecue grills.
Higher Standards-RRG-Hot Tub- Hand Crafted Detail

Higher Standards-RRG-Hot Tub- Hand Crafted Detail

Campton KY
Get rates
A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave Winchester KY
$95 nightly
The price is $105 total per night
$105 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A seasonal outdoor pool and a computer station are also provided.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Montgomery County
View all properties
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.
See properties

Photos of local treasures

Browse Montgomery County vacation photos for more inspiration

A river winding through a densely forested valley with rocky cliffs on one side.

Frequently asked questions

How much are vacation packages to Montgomery County?
With offers starting from as little as $552, flight and hotel packages are the perfect way to make your vacation budget stretch further. Montgomery County, here you come!
Where can I get the best vacation package deals for Montgomery County?
It's hard to look past Travelocity when it comes to piecing together your Montgomery County package deal. There are at least 400 air carriers and 1,000,000 properties worldwide to choose from. Plan your escape now and get ready to cross another destination off your to-do list.
Why should I purchase my Montgomery County vacation package via Travelocity?
From our 24/7 customer care to our range of enticing destinations, we are dedicated to giving you the most unforgettable vacation. All you need to do is click and book — our Price Match Guarantee will ensure you get the best price.
Will I save money on my Montgomery County car rental if I book it with hotels and flights?
Definitely. And our Montgomery County vacation packages are the best way to do it. With only a few clicks you can save money and time by combining your bookings. Collect the keys to your rental car and do your vacation your way. Looking for things to do? Throw some tours or experiences into your package and save on those too.
Which airport is best for Montgomery County?
The main airport in Montgomery County is Blue Grass Airport (LEX).

Explore More Ways to Travel with Travelocity