Title: Montgomery Vacation Packages & Trips 2026 from CA $550 | 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) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Montgomery Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 #### 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. ![Courtyard by Marriott Newburgh Stewart Airport](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott Newburgh Stewart Airport CA $550 per person Apr 25 - Apr 27 found 5 hours ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 8.2/10 Very Good! (691 reviews) it was great room and i would go back Reviewed on Jan 14, 2026 ![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 $874 per person Mar 25 - Mar 31 found 1 day ago Roundtrip flight included Calgary (YYC) to Newburgh (SWF) 8.6/10 Excellent! (1,002 reviews) Easy check in, clean and smoke free, friendly staff, nice rooms, hot breakfast; would stay again!!!! Reviewed on Jan 20, 2026 ![Microtel Inn & Suites by Wyndham Middletown](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695948/1e5617f9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Microtel Inn & Suites by Wyndham Middletown CA $940 per person Mar 25 - Mar 31 found 1 day ago Roundtrip flight included Calgary (YYC) to Newburgh (SWF) 7/10 Good! (1,000 reviews) The room was very clean. The staff was welcoming and polite. Not sure about The amenities was only there on a business trip. Overall would definitely stay again. Reviewed on Dec 6, 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 $633 per person Apr 3 - Apr 6 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Newburgh (SWF) 6/10 (1,002 reviews) The rooms are clean and well maintained with a fridge and microwave located inside the room. The staff were accommodating and welcoming. Reviewed on Jan 24, 2026 ![Super 8 by Wyndham Montgomery Maybrook](https://images.trvl-media.com/lodging/1000000/860000/855600/855538/7ac7ec53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Super 8 by Wyndham Montgomery Maybrook CA $609 per person Apr 3 - Apr 6 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Newburgh (SWF) 6.4/10 (1,000 reviews) Breakfast was not all good Reviewed on Dec 16, 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) ### Holiday Inn Express & Suites Montgomery by IHG 2105 Route 208 Montgomery NY Fully refundable CA $121 CA $137 total Feb 22 - Feb 23 includes taxes & fees 8.6/10 Excellent! (820 reviews) Very clean and generously sized room. Staff was very courteous and helpful Reviewed on Jan 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=7814618&PinnedHotelID=7814618&HadPinnedHotel=true®ionId=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 $96 CA $109 total Feb 26 - Feb 27 includes taxes & fees 6.2/10 (1,000 reviews) Nice place Reviewed on Nov 18, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%2F02%2F2026&selected=855538&PinnedHotelID=855538&HadPinnedHotel=true®ionId=8728) ![Borland House Inn](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/47637293_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Borland House Inn 130 Clinton Street Montgomery NY 9.2/10 Wonderful! (149 reviews) Lovely antique home beautifully cared for. We felt comfy and safe. Fun little pub down the street. Breakfast was delicious! Reviewed on Jan 28, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=11796055&PinnedHotelID=11796055&HadPinnedHotel=true®ionId=8728) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=11796055&PinnedHotelID=11796055&HadPinnedHotel=true®ionId=8728) [See all 1,238 properties in Montgomery](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=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) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app