Montgomery County Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Montgomery County

A person on a bicycle in a stone tunnel with moss-covered walls.
FlightsFlightsHotelsHotels

High Hill

High Hill

Top hotels in Montgomery County

Knights Inn New Florence

Knights Inn New Florence

2 out of 5
Booneslick Road, 403, 403 New Florence MO
The price is S$189 per night from 16 Nov to 17 Nov
S$189
16 Nov - 17 Nov
includes taxes & fees
6.8/10 (602 reviews)
"Needs a good cleaning. Breakfast was lacking.Shower made an awful noise. Check in gal was nice and bed was comfortable."

Reviewed on 25 Oct, 2026

Knights Inn New Florence
The Mercantile on the Katy Trail

The Mercantile on the Katy Trail

4.5 out of 5
500 Walnut St Hermann MO
The price is S$265 per night from 8 Dec to 9 Dec
S$265
8 Dec - 9 Dec
includes taxes & fees
9.8/10 Exceptional! (45 reviews)
"Great decor, they decorated it with the age of the building. The Katy Trail was directly behind it. The owner was quick to respond with requests etc. They had half a dozen eggs and a few beers in the frige for guests, excellent touch. Two areas of concern was the old style of bath tub fit the decor ..."

Reviewed on 12 Nov, 2026

The Mercantile on the Katy Trail
Bay Inn & Suites Troy

Bay Inn & Suites Troy

2.5 out of 5
107 King Dr Troy MO
The price is S$106 per night from 7 Dec to 8 Dec
S$106
7 Dec - 8 Dec
includes taxes & fees
9.2/10 Wonderful! (66 reviews)
"Very clean and new looking, but no one ever at the desk. If you needed anything (extra towel, toilet paper, do not disturb sign) [things we had to ask for] you had to hunt for someone who worked there. There was lots of channels o the TV, but no TV schedule. You had to just scroll."

Reviewed on 12 Nov, 2026

Bay Inn & Suites Troy
See all 549 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?
Our Montgomery County packages, which begin from just , are an ideal way to save big bucks. Pick and choose your favourite hotels, flights and more to create a personalised trip.
How do I get a cheap travel package to Montgomery County?
If you love getting an amazing deal, bundle your bookings into a Montgomery County holiday package. Whether you need flights, hotels, tours or rental cars, you can browse and book them all in one place. You'll have a wealth of choice at your fingertips too. Expedia has more than 550 airlines and 1,000,000 hotel options worldwide to select from. Fly with who you prefer, stay anywhere you like and save some cash — now that's the perfect holiday!
What are the top hotels in Montgomery County?
When it comes to hotels in New Florence, Knights Inn New Florence and Motel 70 are two fantastic options. If you're also heading to Rhineland, Americas Best Value Inn New Florence and Colonial Inn will make you feel right at home.
How far in advance should I book my Montgomery County holiday?
It's difficult to pick the best time for airfares, but we generally suggest the earlier, the better. Many international flights on Expedia become available to compare up to a year in advance. If you're booking last minute, don't despair. Bargain prices appear from time to time within a few weeks of departure dates.
What does an Expedia Montgomery County travel package include?
With Expedia, you can select any combination of flights, hotels and car rentals to build your ideal Montgomery County package. Once you've made your booking, you can add on all the fun stuff like tours and activities. Don't forget, the more you bundle, the bigger the savings!
What should I know before booking a Montgomery County travel package?
A travel package can be tailored to your budget and is a fantastic way to stretch your hard-earned dollars. How much you include is your call. Rental cars, hotels and flights — come up with a combination that suits your style.
Can I choose my airline with a Montgomery County Expedia holiday package?
You can. Expedia has access to more than 550 partner airlines around the world, so go with the carrier that best fits your travel preferences.
If I'm not able to travel, can I cancel my Montgomery County holiday package?
We totally get it — sometimes life doesn't go according to plan. If you've booked a Montgomery County holiday package and need to cancel or change it, we're here to help. We suggest looking up our Customer Service Portal first for information. But generally speaking, if you've booked your package within 24 hours, you may be able to cancel or change your itinerary free of charge. If it's been more than 24 hours, your airline, hotel or car rental company may charge a fee.

Stay near popular Montgomery County attractions

Endless Summer Winery

9.0/10 (34 reviews)
You can enjoy a tasting or tour at Endless Summer Winery during your travels to Hermann. You can enjoy the wineries while in the area.
See properties

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.