Montgomery County Vacation Packages

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Your Montgomery County Vacation

Reserve a vacation package to Montgomery County and make planning your getaway easy. With the logistics arranged before you leave, you can focus on enjoying every second in this amazing destination. You can expect to have a to-do list as long as your arm during your trip to Montgomery County. One leading city you'll want to spend some time exploring is Litchfield. Whether you're travelling on a budget or in the lap of luxury, Expedia are here to help you tailor-make your next Montgomery County vacation.

Top Montgomery County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was CA $1,293, price is now CA $906 per person
CA $906
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Louis (STL)
9.2/10 Wonderful! (1,661 reviews)
Nice quiet

Reviewed on Jul 10, 2026

Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
Price was CA $1,303, price is now CA $1,019 per person
CA $1,019
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Louis (STL)
9/10 Wonderful! (1,984 reviews)
.

Reviewed on Jul 10, 2026

The Cheshire

The Cheshire

4 out of 5
Price was CA $1,313, price is now CA $1,027 per person
CA $1,027
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Louis (STL)
8.8/10 Excellent! (1,001 reviews)
A majority of the staff was friendly and helpful. Love the literary themes. Had a great stay and would definitely visit again.

Reviewed on Jul 12, 2026

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Price was CA $1,166, price is now CA $932 per person
CA $932
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Louis (STL)
8.4/10 Very good! (831 reviews)
Very clean and very nice as a little home away from home. It’s just up the road from shops and all kinds of restaurants. When I make another trip back up there this will be my first choice again!!

Reviewed on Jul 7, 2026

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was CA $1,382, price is now CA $1,137 per person
CA $1,137
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Really nice rooms

Reviewed on Jul 13, 2026

Montgomery County Hotel Deals

Baymont by Wyndham Litchfield

Baymont by Wyndham Litchfield

2.5 out of 5
1405 W Hudson Dr Litchfield IL
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Jul 14 to Jul 15
CA $140
CA $154 total
Jul 14 - Jul 15
includes taxes & fees
8.2/10 Very good! (1,008 reviews)
"Staff was so nice and place was clean love the place will definitely stay again"

Reviewed on Jul 12, 2026

Baymont by Wyndham Litchfield
Holiday Inn Express & Suites Litchfield West by IHG

Holiday Inn Express & Suites Litchfield West by IHG

2.5 out of 5
4 Thunderbird Circle Litchfield IL
Fully refundable
The price is CA $161 per night from Jul 26 to Jul 27
CA $161
CA $177 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (638 reviews)
"Great room"

Reviewed on Jul 11, 2026

Holiday Inn Express & Suites Litchfield West by IHG
Quality Inn Litchfield Route 66

Quality Inn Litchfield Route 66

2.5 out of 5
1010 E Columbian Blvd N Litchfield IL
Fully refundable
The price is CA $126 per night from Jul 19 to Jul 20
CA $126
CA $139 total
Jul 19 - Jul 20
includes taxes & fees
8.6/10 Excellent! (654 reviews)
"Night staff was awesome. Morning receptionist was very unfriendly. Room was great except the ants in our food on the counter in the morning. Thank goodness we had them sealed up so they didn’t get into it. We tried to tell the front desk staff about it but she said she couldn’t help."

Reviewed on Jul 10, 2026

Quality Inn Litchfield Route 66
See all 214 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Montgomery County vacation package cost?
Say yes to new adventures with our Montgomery County vacation packages, which start from just CA $906. Pick the flights and hotels that suit your style. Then, add on a few sightseeing activities for a memorable escape.
How do I get a cheap travel package to Montgomery County?
Lock in flights that fit your schedule, add a hotel to your booking and watch how much you save with a Montgomery County vacation package. It's as easy as that! From flights and hotels to rental cars and activities, Expedia makes traveling cheap and easy. And with more than 550 partner airlines and 1,000,000 hotels throughout the world to pick from, you won't be short of choice.
What are the top hotels in Montgomery County?
Take a look at State House Inn and Best Western Plus Champaign/Urbana Inn. They're top picks for many travelers headed to Litchfield. If Nokomis features in your travel itinerary, Quality Inn Litchfield Route 66 and Hampton Inn Litchfield are both popular options.
How far in advance should I book my Montgomery County vacation?
Be rewarded with the widest variety at the lowest prices by booking your Montgomery County adventure early. Air carriers usually sell tickets anywhere up to a year before departure, so reserve your spot as soon as possible. That being said, Expedia is committed to giving you the best bargains around, so it's never a bad time to book your dream vacation!
What does an Expedia Montgomery County travel package include?
That depends entirely on you. You can choose from a range of Montgomery County bundles, such as a hotel, flight and rental car. You can also book a flight with a hotel, or a flight and a rental car. Once you've made your booking, you can add on the fun stuff like experiences and activities. Whatever your perfect Montgomery County vacation looks like, get ready to save!
What should I know before booking a Montgomery County travel package?
Bundling your bookings into a Montgomery County vacation package is the easiest way to organize your trip. Not only that, you'll get great discounts just for combining your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Montgomery County Expedia vacation package?
Yes, you can. We have more than 550 partner airlines worldwide, so select the carrier that fits your needs.
If I'm not able to travel, can I cancel my Montgomery County vacation package?
It's impossible to predict what the future holds, so it's good to know that you can change or cancel your Montgomery County vacation package. If you booked in the last 24 hours, you may be eligible for a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for more information.

Stay near popular Montgomery County attractions

Litchfield Museum and Route 66 Welcome Center

7.8/10 (26 reviews)
You can spend an afternoon exploring the galleries in Litchfield Museum and Route 66 Welcome Center during your travels in Litchfield. While you're here, you can savor the top-notch restaurants.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.