Title: Montgomery Vacation Packages & Trips 2026 from CA $487 | Expedia.ca

[Hotels in Montgomery](https://expedia.ca/Montgomery-Hotels.d8728.Travel-Guide-Hotels)[Vacation Rentals in Montgomery](https://expedia.ca/Montgomery-Vacation-Rentals.d8728.Travel-Guide-VacationRentals)[Things to do in Montgomery](https://expedia.ca/Things-To-Do-In-Montgomery.d8728.Travel-Guide-Activities)[Montgomery Car Rentals](https://expedia.ca/Car-Rentals-In-Montgomery.d8728.Car-Rental-Guide)

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# Montgomery Vacation Packages

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#### Your Montgomery Vacation

The vibrant city of Montgomery is calling. Discover its highlights and hidden gems with a Montgomery vacation package that's customized to you. A trip to Montgomery is a terrific opportunity to sightsee. Be sure to visit big-name attractions such as [Angry Orchard](https://www.expedia.ca/Angry-Orchard-Walden.d553248635998039554.Vacation-Attraction), [Thomas Bull Memorial Park](https://www.expedia.ca/Thomas-Bull-Memorial-Park-Campbell-Hall.d553248621555565638.Vacation-Attraction) and [Orange County Arboretum](https://www.expedia.ca/Orange-County-Arboretum-Campbell-Hall.d553248621558786501.Vacation-Attraction). Whoever you're going away with and whether your budget is big or small, your dream Montgomery vacation is just a few clicks away with Expedia.

## Top Montgomery Vacation Deals

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

![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sleep Inn & Suites Middletown - Goshen

CA $487

per person

Feb 13 - Feb 15

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Newburgh (SWF)

8.6/10 Excellent! (1,002 reviews)

Brutal cold while I was there. The heater in the rest room didn’t work. Asked the desk to have it fixed on the first day. Not fixed. 3 days, Staff didn’t bother to reach back out to me for an update.

Reviewed on Dec 17, 2025

![The Crossroads Hotel, Newburgh](https://images.trvl-media.com/lodging/1000000/20000/14500/14410/5440914b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Crossroads Hotel, Newburgh

CA $551

per person

Jan 16 - Jan 18

found 16 hours ago

Roundtrip flight included

Ottawa (YOW) to Newburgh (SWF)

7.2/10 Good! (679 reviews)

Room was clean, bed & pillows were comfortable. Carpets in hallway were dirty. Housekeepers did not leave wash cloths when making room. Overall ok if all you need is a place to sleep

Reviewed on Nov 30, 2025

![Newburgh Inn](https://images.trvl-media.com/lodging/1000000/10000/1700/1692/39bbd1ec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Newburgh Inn

CA $531

per person

Jan 16 - Jan 18

found 16 hours ago

Roundtrip flight included

Ottawa (YOW) to Newburgh (SWF)

5.4/10 (111 reviews)

I have wondering things to say about my enjoying everything regards my choice to book & stay at The Red Roof Roof Hotel & Suites in Newburgh, NY. The staff is outstanding. They all are professional & friendly. It’s a safe, clean hotel. The bonuses at this particular hotel include gorgeous sunrises & sunsets. Overlooking a lake that faces east. I highly recommend choosing The Red Roof when in this area. Sincerely, Jeannine C

Reviewed on Nov 10, 2025

![Howard Johnson by Wyndham Newburgh/West Point](https://images.trvl-media.com/lodging/1000000/10000/7700/7652/8a35f36a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Howard Johnson by Wyndham Newburgh/West Point

CA $541

per person

Jan 16 - Jan 18

found 16 hours ago

Roundtrip flight included

Ottawa (YOW) to Newburgh (SWF)

6/10 (1,002 reviews)

clean room great staff

Reviewed on Nov 28, 2025

![Super 8 by Wyndham Newburgh/West Point Near Stewart Airport](https://images.trvl-media.com/lodging/1000000/460000/459800/459793/de8a644e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

CA $531

per person

Jan 16 - Jan 18

found 16 hours ago

Roundtrip flight included

Ottawa (YOW) to Newburgh (SWF)

5.4/10 (1,002 reviews)

Everything was perfect. The room was very nice, clean and comfortable. Staff was very welcoming, friendly and helpful..

Reviewed on Dec 15, 2025

## Ready to book your vacation to Montgomery?

Choose your dates

## Montgomery Hotel Deals

![Holiday Inn Express & Suites Montgomery by IHG](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Holiday Inn Express & Suites Montgomery by IHG

2105 Route 208 Montgomery NY

Fully refundable

CA $124

CA $140 total

Jan 4 - Jan 5, 2026

includes taxes & fees

8.6/10 Excellent! (796 reviews)

clean and warm

Reviewed on Dec 14, 2025

[](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=7814618&PinnedHotelID=7814618&HadPinnedHotel=true&regionId=8728)

![Super 8 by Wyndham Montgomery Maybrook](https://images.trvl-media.com/lodging/1000000/860000/855600/855538/7ac7ec53_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Super 8 by Wyndham Montgomery Maybrook

207 Montgomery Rd Montgomery NY

Fully refundableReserve now, pay when you stay

CA $110

CA $124 total

Jan 1 - Jan 2, 2026

includes taxes & fees

6.2/10 (1,008 reviews)

Nice place

Reviewed on Nov 18, 2025

[](https://expedia.ca/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%2F01%2F2026&selected=855538&PinnedHotelID=855538&HadPinnedHotel=true&regionId=8728)

![Borland House Inn](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/47637293_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Borland House Inn

130 Clinton Street Montgomery NY

9.2/10 Wonderful! (144 reviews)

I arrived on a dark and windy night and was immediately welcomed with coziness and warmth. Next time I hope to meet the corgis who are part of the management team.

Reviewed on Nov 23, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=11796055&PinnedHotelID=11796055&HadPinnedHotel=true&regionId=8728)

[](https://expedia.ca/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=11796055&PinnedHotelID=11796055&HadPinnedHotel=true&regionId=8728)

[See all 1,240 properties in Montgomery](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=18%2F12%2F2025&endDate=19%2F12%2F2025&regionId=8728)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

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