Montgomery County Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Montgomery County

Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 out of 5
2135 Natural Bridge Road Slade KY
8.4/10 Very Good! (1,794 reviews)
Clean rooms

Reviewed on 16 Jan 2026

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Natural Bridge State Resort Park
Black Bear Lodge Motel

Black Bear Lodge Motel

2.5 out of 5
781 Natural Bridge Rd Slade KY
8/10 Very Good! (638 reviews)
The bridge was very pot-holey. They need filled in.

Reviewed on 23 Dec 2025

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Black Bear Lodge Motel
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave Winchester KY
Fully refundableReserve now, pay when you stay
The price is 1.897.384 ₫ per night from 26 Jan to 27 Jan
1.897.384 ₫
2.091.676 ₫ total
26 Jan - 27 Jan
includes taxes & fees
8.4/10 Very Good! (999 reviews)
Room was fine. Staff was nice. Didn’t eat breakfast because we had a brunch to go to.

Reviewed on 14 Dec 2025

Best Western Winchester Hotel
See all 852 properties in Montgomery County
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.

Frequently asked questions

How much does a Montgomery County holiday package cost?
Much less than you might think — from a tempting , in fact! By bundling hotels, flights and car rentals into a custom-made package, your trip to Montgomery County is only clicks away.
How do I get a cheap travel package to Montgomery County?
You'll save piles of cash if you bundle your flights, car rentals and hotels into a Montgomery County holiday package. Sometimes cheap means fewer choices. But not with Expedia. We offer more than 550 airlines and 1null000null000 hotels across the globe, which means you'll always have plenty of options to choose from. Want to save even more? Add some fun activities to your package deal and unlock even more bargains! After all, travel is about more than just getting to your destination.
What are the top hotels in Montgomery County?
Look up Holiday Inn Express & Suites Mt Sterling North, an IHG Hotel and Ramada Limited Mount Sterling. They're the first choice for lots of travellers to Mount Sterling. If Jeffersonville is on your travel itinerary, Comfort Inn and Suites and Budget Inn are a couple of popular options.
How far in advance should I book my Montgomery County holiday?
While prices do change, we generally suggest booking your holiday as early as possible. Most international fares are found on Expedia up to 12 months in advance. If circumstances have left you booking last minute, you might still get lucky. Cheap journeys to Montgomery County sometimes appear only weeks before departure.
What does an Expedia Montgomery County travel package include?
Expedia has everything you need to book your Montgomery County escape, but what goes into your package is your call. Select from a combination of flights, hotels and rental cars. In search of a few activities to fill in your time? Once you've made your booking, you can add them too. No matter your style or budget, there's a holiday package to match your needs.
What should I know before booking a Montgomery County travel package?
Get set to save with an Expedia travel package. Combine your airfares, rental cars and hotels and unlock terrific discounts. You're not restricted to hotels, though. We have oceanfront condos, creek-side mountain cabins and even glamping tents!
Can I choose my airline with a Montgomery County Expedia holiday package?
With a holiday package, you're the one in charge. Whether you're looking to fly to Montgomery County in economy or business class, simply select from the available airline options. Expedia has access to more than 550 airline partners throughout the world.
If I'm not able to travel, can I cancel my Montgomery County holiday package?
Don't worry if you're rethinking your Montgomery County holiday package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We realise life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.