Title: Hillside Vacation Packages & Trips 2026 from CA $1,321 | Expedia.ca [Hotels in Hillside](https://expedia.ca/Hillside-Hotels.d553248635975855399.Travel-Guide-Hotels)[Vacation Rentals in Hillside](https://expedia.ca/Hillside-Vacation-Rentals.d553248635975855399.Travel-Guide-VacationRentals)[Hillside Car Rentals](https://expedia.ca/Car-Rentals-In-Hillside.d553248635975855399.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Hillside 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 ## Top Hillside Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Ogunquit River Inn & Suites](https://images.trvl-media.com/lodging/2000000/1200000/1198100/1198069/6221f2a7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ogunquit River Inn & Suites CA $1,321 per person Jun 2 - Jun 8 found 1 day ago Roundtrip flight included Montreal (YUL) to Portland (PWM) 9/10 Wonderful! (1,000 reviews) The room was very clean! Reviewed on Oct 31, 2025 ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/1a7f326f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Harbor Hotel Downtown Portland CA $1,927 per person Jun 2 - Jun 8 found 1 day ago Roundtrip flight included Montreal (YUL) to Portland (PWM) 9.2/10 Wonderful! (1,776 reviews) Nice hotel. From check in to check out, we had everything we needed and pleasant and informed staff to help us enjoy our stay Reviewed on Mar 18, 2026 ![The Docent's Collection at 121 Middle Street](https://images.trvl-media.com/lodging/39000000/38780000/38770100/38770068/148140d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Docent's Collection at 121 Middle Street Downtown Portland CA $2,207 per person Jun 2 - Jun 8 found 1 day ago Roundtrip flight included Montreal (YUL) to Portland (PWM) 9.6/10 Exceptional! (275 reviews) Checks all the boxes for location, style, space, clean, secure and even the box for "exceeds all expectations"! Reviewed on Mar 18, 2026 ![The Kennebunk Inn](https://images.trvl-media.com/lodging/2000000/1200000/1190600/1190587/68e19a4a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Kennebunk Inn CA $1,356 per person Jun 2 - Jun 8 found 1 day ago Roundtrip flight included Montreal (YUL) to Portland (PWM) 7.8/10 Good! (753 reviews) I would visit again Reviewed on Dec 4, 2025 ## Ready to book your vacation to Hillside? Choose your dates ## Hillside Hotel Deals ![Hampton Inn Oxford](https://images.trvl-media.com/lodging/16000000/15840000/15835200/15835107/ac3c9d7b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Oxford 151 Main St Oxford ME Fully refundableReserve now, pay when you stay CA $133 CA $145 total Mar 29 - Mar 30 includes taxes & fees 9/10 Wonderful! (1,003 reviews) I was very satisfied, it was a 1 day stay. Staff was friendly, room was clean , breakfast was Great! No complaints Reviewed on Mar 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=15835107&PinnedHotelID=15835107&HadPinnedHotel=true®ionId=553248635975855399) ![Dormir](https://images.trvl-media.com/lodging/10000000/9320000/9312400/9312400/eaaa6212_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Dormir 965 Roosevelt Trail Windham ME Fully refundableReserve now, pay when you stay CA $135 CA $147 total Mar 29 - Mar 30 includes taxes & fees 8.8/10 Excellent! (1,000 reviews) Enjoyed my stay. Very reliable. Reviewed on Mar 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=9312400&PinnedHotelID=9312400&HadPinnedHotel=true®ionId=553248635975855399) ![Oxford Casino Hotel](https://images.trvl-media.com/lodging/36000000/35190000/35183100/35183095/c9a0432b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Oxford Casino Hotel 777 Casino Way Oxford ME Fully refundableReserve now, pay when you stay CA $159 CA $174 total Mar 23 - Mar 24 includes taxes & fees 8.6/10 Excellent! (1,002 reviews) We arrived at noon and were told that we would have to pay and extra $30+ to check-in early, even though there were rooms available. Food was expensive based on the quality. Reviewed on Mar 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F03%2F2026&endDate=24%2F03%2F2026&selected=35183095&PinnedHotelID=35183095&HadPinnedHotel=true®ionId=553248635975855399) [See all 1,306 properties in Hillside](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=22%2F03%2F2026&endDate=23%2F03%2F2026®ionId=553248635975855399) 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