Deals on vacations and trips to Montgomery County

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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.
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
Price was $853, price is now $788 per person
$788
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Lexington (LEX)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the indoor pool and conveniences like a 24-hour front desk and laundry facilities.
Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was $1,179, price is now $1,053 per person
$1,053
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was $1,111, price is now $1,012 per person
$1,012
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
The Delegate

The Delegate

3.5 out of 5
Price was $879, price is now $811 per person
$811
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Lexington (LEX)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Self parking and express check-out are also offered on site.
Holiday Inn Express & Suites Lexington W - Versailles by IHG

Holiday Inn Express & Suites Lexington W - Versailles by IHG

2.5 out of 5
Price was $916, price is now $850 per person
$850
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Lexington (LEX)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Top Montgomery County hotels deals

Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 out of 5
2135 Natural Bridge Road Slade KY
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $117 total per night
$117 total
Sep 13 - Sep 14
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.
Breakfast included
Pet friendly
Black Bear Lodge Motel

Black Bear Lodge Motel

2.5 out of 5
781 Natural Bridge Rd Slade KY
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $97 total per night
$97 total
Sep 13 - Sep 14
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.
Parking included
Air conditioning
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave Winchester KY
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $99 total per night
$99 total
Sep 13 - Sep 14
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
Holiday Inn Express and Suites Morehead by IHG

Holiday Inn Express and Suites Morehead by IHG

2.5 out of 5
2650 KY 801 North Morehead KY
Free Cancellation
$148 nightly
The price is $163 total per night
$163 total
Sep 20 - Sep 21
Total with taxes and fees
An outdoor pool, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like self-serve breakfast and WiFi in public areas. A business center, a picnic area, and free newspapers are also on offer.
Pool
Breakfast included
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr Winchester KY
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $88 total per night
$88 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Value Stay

Value Stay

2 out of 5
5100 Revilo Rd Winchester KY
Free Cancellation
Reserve now, pay when you stay
$53 nightly
The price is $59 total per night
$59 total
Oct 13 - Oct 14
Total with taxes and fees
Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. Luggage storage is also provided.
Pet friendly
Parking included
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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.
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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 $788, 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).

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