Montgomery Vacations from $582

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The Latest Montgomery vacation packages

Price found within the past 48 hours. Click for updated prices.
Homewood Suites by Hilton Windsor Locks Hartford

Homewood Suites by Hilton Windsor Locks Hartford

3 out of 5
Price was $708, price is now $582 per person
$582
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
8.6/10 Excellent! (898 reviews)
Staff was amazing and very helpful.

Reviewed on Sep 20, 2025

Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $1,340, price is now $1,027 per person
$1,027
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
9.8/10 Exceptional! (1,002 reviews)
Clean and convenient

Reviewed on Sep 29, 2025

The Litchfield Inn

The Litchfield Inn

4 out of 5
Price was $1,350, price is now $1,057 per person
$1,057
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Sarasota (SRQ) to Hartford (BDL)
9/10 Wonderful! (942 reviews)
The Litchfield Inn was very nice and quaint! Judy at the Front Desk was amazing and so accommodating. Will definitely stay again.

Reviewed on Sep 29, 2025

DoubleTree by Hilton Hartford Downtown

DoubleTree by Hilton Hartford Downtown

4 out of 5
Downtown Hartford
Price was $901, price is now $723 per person
$723
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
7.6/10 Good! (1,005 reviews)
It was walking distance to the concert we where going to. Along with I think that all hotels should have parking for their guest. Why should we have to pay for parking when we are already paying to stay at hotel just greedy for money.

Reviewed on Aug 9, 2025

9 Academy

9 Academy

4 out of 5
Save 100% on your flight
Price was $1,180, price is now $955 per person
$955
per person
Dec 4 - Dec 7
found 17 hours ago
Roundtrip flight included
Tampa (TPA) to Hartford (BDL)
8.6/10 Excellent! (7 reviews)
The Loft was so beautifully decorated and every detail was perfect.

Reviewed on Oct 8, 2024

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Montgomery Hotel Deals

MGM Springfield

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA
$179 nightly
The price is $203 total per night from Oct 7 to Oct 8
$203 total
Oct 7 - Oct 8
Total with taxes and fees
8.8/10 Excellent! (1,416 reviews)
"To much walking around casino with fencing"

Reviewed on Sep 30, 2025

MGM Springfield
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

2 out of 5
185 Ella Grasso Turnpike, Windsor Locks, CT
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $77 total per night from Oct 5 to Oct 6
$77 total
Oct 5 - Oct 6
Total with taxes and fees
6.6/10 (1,567 reviews)
"Convenient from airport. Quiet and clean, nice room Breakfast was perfect!"

Reviewed on Sep 29, 2025

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport

4 out of 5
16 Ella T. Grasso Turnpike, Windsor Locks, CT
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $165 total per night from Oct 12 to Oct 13
$165 total
Oct 12 - Oct 13
Total with taxes and fees
8/10 Very Good! (1,034 reviews)
"Nice"

Reviewed on Sep 25, 2025

DoubleTree by Hilton Hartford - Bradley Airport
See all 481 properties in Montgomery
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.

Montgomery Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
670

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Frequently asked questions

How much does a Montgomery vacation package cost?
You'll find cheap prices from $582 on Expedia for your Montgomery escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Montgomery costs.
What are the cheapest months to go to Montgomery?
If you're looking to book a cheap Montgomery vacation package, consider planning a trip in November, December and January. You'll typically find better prices on accommodations and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Montgomery?
The ideal length of your Montgomery vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you enough time to check out all the main attractions and discover some hidden gems along the way.
How to find the best Montgomery package deals?
Start your search for a Montgomery package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Montgomery package deal right away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Montgomery escape underway.
Is it cheaper to book a Montgomery vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking accommodations and flights individually. Better still, you can customize your Montgomery escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Montgomery?
If you've got your Montgomery vacation dates confirmed, book as soon as you can to score some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Montgomery vacation packages?
Set off on your perfect escape to Montgomery with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until your next payday — we've partnered with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no hidden or late payment fees, you can easily budget for your trip and snap up cheap deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.