Montgomery Holidays from £455

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    Save up to £335 when you book a flight and hotel together*
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Your Montgomery Holiday

The vibrant city of Montgomery is calling. Discover its highlights and hidden gems with a Montgomery holiday package that's customised to you. A trip to Montgomery is a terrific opportunity to sightsee. Be sure to visit big-name attractions such as Angry Orchard, Thomas Bull Memorial Park and Orange County Arboretum. Whoever you're going away with and whether your budget is big or small, your dream Montgomery holiday is just a few clicks away with Expedia.

Top Montgomery Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
9 Sept - 12 Sept
found 14 hours ago
Return flight included
London (LGW) to Newburgh (SWF)
7.4/10 Good! (502 reviews)
Comfortable place to stay

Reviewed on 7 Aug 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
per person
9 Sept - 12 Sept
found 14 hours ago
Return flight included
London (LGW) to Newburgh (SWF)
8.4/10 Very Good! (1,006 reviews)
I stay at the Red roof Inn often and this is my favorite local hotel. I highly recommend anyone coming to the area to check the rates and come to the Red roof Inn because I promise you you will not be disappointed. 💙

Reviewed on 9 Aug 2025

Montgomery Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
4,600
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Brotherhood Winery, Angry Orchard and Castle Fun Centre

Top hotels in Montgomery

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

2.5 out of 5
2105 Route 208, Montgomery, NY
Fully refundable
The price is £96 per night from 28 Aug to 29 Aug
£96
28 Aug - 29 Aug
includes taxes & fees
8.6/10 Excellent! (748 reviews)
"Easy check in, clean room. Coffee area needed cleaning."

Reviewed on 8 Aug 2025

Holiday Inn Express & Suites Montgomery by IHG
Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
207 Montgomery Rd, Montgomery, NY
Fully refundableReserve now, pay when you stay
The price is £67 per night from 7 Sept to 8 Sept
£67
7 Sept - 8 Sept
includes taxes & fees
6.2/10 (1,005 reviews)
"Good"

Reviewed on 31 Jul 2025

Super 8 by Wyndham Montgomery Maybrook
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
555 Resorts World Drive, Monticello, NY
Fully refundableReserve now, pay when you stay
The price is £175 per night from 7 Sept to 8 Sept
£175
7 Sept - 8 Sept
includes taxes & fees
8/10 Very Good! (1,619 reviews)
"Was an enjoyable resort. Plenty of activities foe children."

Reviewed on 7 Aug 2025

The Kartrite Resort & Indoor Waterpark
See all 1,205 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

Why should I book my Montgomery holiday with Expedia?
Expedia has your back for every detail of your upcoming Montgomery holiday. You'll always get the best deals, but when you bundle your accommodation, flights and/or car hire into a holiday package, you can save even more. Want to really make the most of your escape? Add a few exciting activities and tours to your package. We offer flexible cancellation policies on most bookings, so you won't need to worry if your travel plans change. Visit our Customer Service Portal link to discover more.
When is the best time of year to holiday in Montgomery?
July, October and November are the busiest months in Montgomery, while January, August and December are generally quieter. Organise your trip to Montgomery based on what type of holiday you're looking for. January is the coolest time of year, when daytime temperatures average -3ºC. In July, the warmest period, expect averages of 22ºC during the day.
What is the top hotel for my holiday in Montgomery?
Create lasting memories in Montgomery by choosing Super 8 by Wyndham Middletown as your gateway to fun and adventure.
How do I get a cheap holiday to Montgomery?
Combine your bookings with Expedia to save on your next adventure. With over 400 airlines and 321,000 properties around the globe, your Montgomery holiday can be customised exactly to suit your budget. With all that extra cash, why not add some exciting tours and activities? It's an easy way to unlock even more discounts. That dream holiday to Montgomery is much closer than you thought! Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Montgomery holiday?
Ensure your holiday in Montgomery is an unforgettable one by taking in its best attractions. Angry Orchard, Brotherhood Winery, Ice Time Sports Complex and Resorts World Hudson Valley are among the things worth discovering while you're in the city.
What is the best area to stay in when on holiday in Montgomery?
There's so much to do in Montgomery, so stay near its top sights and treat yourself to more time sightseeing. Orange County Arboretum is one place to add to your to-do list.
Do I need a visa for my Montgomery holiday?
Official government websites are the best source of information on visa requirements, application procedures and necessary documentation. Your nationality and reason for visiting, whether it be for tourism or business, will determine if you need a visa for Montgomery. Also double-check that your passport is up to date and has a minimum of six months validity remaining after your intended return date. Do all your travel planning well in advance to avoid any nasty last-minute surprises.
What should I wear on my Montgomery holiday?
Consider the types of activities you'll be doing during your trip to Montgomery and create a travel wardrobe that you can mix and match. For fashion inspiration or information on any dress codes, browse style blogs or relevant social media accounts. Take a look at the local weather forecast so you can pack your bags accordingly. The warmest time of year in Montgomery is July, with average daytime temperatures of 22ºC. If you're holidaying during the coolest month of January, the mercury averages -3ºC during the day.
What does an Expedia Montgomery holiday include?
Expedia has everything you need to plan your Montgomery trip, but what goes into your package depends on you. Choose from any combination of flights, hire cars and hotels. Looking for some activities to keep you on the move? Once you've made your booking, you can add them too. Whatever your budget or style, there's a holiday package to suit your needs. Private holiday homes and apartments are a few popular property types in Montgomery. Whatever your holiday style or group size, you can count on Expedia for the flexibility and freedom to tailor your dream escape.
Does Expedia offer Book Now, Pay Later Montgomery holidays?
Yes, we do. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in instalments. Simply pick the payment plan best suited to your needs during the checkout process and take away the stress of budgeting for your next trip. Don't forget to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:

  • Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna can help. Paying in easy monthly instalments will make that dream holiday possible.
  • No-deposit holidays: If not paying ahead of time for your getaway makes pressing that "book now" button easier, opt for a no-deposit holiday plan with Klarna so you can Book Now, Pay Later!

Can I choose my airline with a Montgomery Expedia holiday?
Expedia has access to more than 400 partner airlines worldwide, so you definitely can. Simply select the carrier that suits you and craft your ideal Montgomery getaway.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.