Title: Hillside Vacation Packages & Trips 2025/2026 from CA $1,306 | 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. ![Hampton Inn Portland Downtown - Waterfront](https://images.trvl-media.com/lodging/5000000/4490000/4480300/4480291/1dc67cbc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn Portland Downtown - Waterfront Downtown Portland CA $1,306 per person Nov 8 - Nov 12 found 16 hours ago Roundtrip flight included Saskatoon (YXE) to Portland (PWM) 8.8/10 Excellent! (1,005 reviews) Very clean rooms - great staff / excellent location Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-08/2025-11-12/?FromAirport=YXE&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=4480291&paandie=true&dealMarker=VmzHMI7V6TGtEURhW0Q75rHCy9fjrd_H_HPg6WeHxTxT6FFUkmFFNCtu5SFAJTq2) ![Cliff House Maine](https://images.trvl-media.com/lodging/4000000/3990000/3981200/3981160/eb122fc0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cliff House Maine CA $1,964 per person Nov 8 - Nov 12 found 16 hours ago Roundtrip flight included Saskatoon (YXE) to Portland (PWM) 9.4/10 Exceptional! (1,007 reviews) Beautiful hotel & grounds. View from my room was breathtaking Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-08/2025-11-12/?FromAirport=YXE&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=3981160&paandie=true&dealMarker=h7CC-I8ZH6cp-pv79agbc-IXANytFruPXjcPjXY_1ent6lLSDa0je66JB4K-f9t3) ![The Weldon Hotel](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/38875013_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Weldon Hotel Downtown Portland CA $1,389 per person Nov 8 - Nov 12 found 16 hours ago Roundtrip flight included Saskatoon (YXE) to Portland (PWM) 9.8/10 Exceptional! (79 reviews) Great spot, large space, cool design, clean, easy to walk all over town. Reviewed on Oct 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-08/2025-11-12/?FromAirport=YXE&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=107321604&paandie=true&dealMarker=h7CC-I8ZH6cp-pv79agbc9jr_uPBUZdyFtsqaHh6qloHwxY4tWKOU5Jnn7iaWy3i) ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Harbor Hotel Downtown Portland CA $1,321 per person Nov 8 - Nov 12 found 16 hours ago Roundtrip flight included Saskatoon (YXE) to Portland (PWM) 9.2/10 Wonderful! (1,581 reviews) Very nicely appointed hotel in the heart of Portland. The courtyard with fire is a lovely feature. Rooms very comfortable. Coffee maker on our floor wasn't working, but that's my only complaint. Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-08/2025-11-12/?FromAirport=YXE&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=898621&paandie=true&dealMarker=VmzHMI7V6TGtEURhW0Q75rHCy9fjrd_H_HPg6WeHxTyiu3ooxpqem8uhMM6-vpI6) ![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Regency Hotel & Spa Downtown Portland CA $1,394 per person Nov 8 - Nov 12 found 16 hours ago Roundtrip flight included Saskatoon (YXE) to Portland (PWM) 9.4/10 Exceptional! (1,424 reviews) The Regency is the perfect blend of old fashioned ambiance with modern amenities. The most comfortable bed of any place we’ve stayed in, good food and welcoming people all made this a special experience! Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-08/2025-11-12/?FromAirport=YXE&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=920050&paandie=true&dealMarker=VmzHMI7V6TGtEURhW0Q75rHCy9fjrd_H_HPg6WeHxTxtAExkgbonlqMF9ngSg45T) ## Ready to book your vacation to Hillside? Choose your dates ## Hillside Hotel Deals ![Oxford Casino Hotel](https://images.trvl-media.com/lodging/36000000/35190000/35183100/35183095/65811dd1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Oxford Casino Hotel 777 Casino Way, Oxford, ME Fully refundableReserve now, pay when you stay CA $175 CA $190 total Oct 5 - Oct 6 includes taxes & fees 8.6/10 Excellent! (1,000 reviews) Nice hotel "Nice hotel, very comfortable! The restaurant was good but the service was terrible. There was a bit of construction going on, but I wouldn’t ding them on that. I would stay there again. Friendly hotel staff, very comfortable beds." Reviewed on Sep 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=05%2F10%2F2025&endDate=06%2F10%2F2025&selected=35183095&PinnedHotelID=35183095&HadPinnedHotel=true®ionId=553248635975855399) ![Dormir](https://images.trvl-media.com/lodging/10000000/9320000/9312400/9312400/1c6ce74e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Dormir 965 Roosevelt Trail, Windham, ME Fully refundableReserve now, pay when you stay CA $156 CA $170 total Nov 2 - Nov 3 includes taxes & fees 8.8/10 Excellent! (1,008 reviews) "Great late check in" Reviewed on Sep 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=9312400&PinnedHotelID=9312400&HadPinnedHotel=true®ionId=553248635975855399) ![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 $168 CA $184 total Oct 13 - Oct 14 includes taxes & fees 8.8/10 Excellent! (1,000 reviews) "I would say our stay was very good, we had 2 dogs with us and hotel was very accommodating. The only thing that I would say maybe it’s just this particular hotel but your website does advertise that there’s a restaurant and a bar now I did see that there was breakfast from 6 to 10 but I was under ..." Reviewed on Sep 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=13%2F10%2F2025&endDate=14%2F10%2F2025&selected=15835107&PinnedHotelID=15835107&HadPinnedHotel=true®ionId=553248635975855399) [See all 1,231 properties in Hillside](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F10%2F2025&endDate=06%2F10%2F2025®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 ![QR code to download the app](data:image/png;base64,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)