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 1 day 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 $640 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 8.6/10 Excellent! (1,002 reviews) Gym equipment not working Reviewed on Feb 7, 2026 ![Sleep Inn & Suites Monroe - Woodbury](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/0db56af9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sleep Inn & Suites Monroe - Woodbury CA $1,041 per person Mar 13 - Mar 20 found 1 day ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 9.4/10 Exceptional! (1,004 reviews) We had a very nice stay. The room was so clean. The staff was Reviewed on Feb 2, 2026 ![Caldwell House Bed & Breakfast](https://images.trvl-media.com/lodging/6000000/5120000/5112000/5111988/fdae1673_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Caldwell House Bed & Breakfast CA $1,819 per person Apr 25 - May 1 found 7 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 9/10 Wonderful! (474 reviews) Great place to stay. Wonderful breakfasts. Gracious and warm hospitality. Reviewed on May 28, 2024 ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Hotel & Suites Chester by IHG CA $783 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 8.4/10 Very Good! (1,003 reviews) Everything was perfect Reviewed on Feb 6, 2026 ## 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 $120 CA $136 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 23 - Feb 24 includes taxes & fees 6.2/10 (1,000 reviews) Nice place Reviewed on Nov 18, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%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=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=11796055&PinnedHotelID=11796055&HadPinnedHotel=true®ionId=8728) [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%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=09%2F02%2F2026&endDate=10%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