Title: Mountain Vacations in Great Diamond Island 2025/2026 | Expedia.ca ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Great Diamond Island Mountain Vacations ## Book a Hotel + Flight or Car together to unlock savings Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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 ## Flight and Mountain hotel deals in Great Diamond Island Price found within the past 48 hours. Click for updated prices. ![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 $856 per person Dec 4 - Dec 7 found 15 hours ago Roundtrip flight included Watertown (ART) to Portland (PWM) 9.2/10 Wonderful! (1,581 reviews) This property was pricey. I called beforehand to see if there was self parking and they said no but that was not true. My biggest complaint is that upon check-in, the woman said she wanted to give us a room upgrade, but ultimately was unsuccessful. She really made it seem like we were unfortunately being put in a crappy room. Reviewed on Oct 13, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-07/?FromAirport=ART&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=898621&paandie=true&HotelClass=40&dealMarker=slxehwrQ_ERWFZJCZmbwHNjvWjhEyILLoRfIWVv_xvHS5xnOWCxDa6N7pTxYRkTg) ![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 $979 per person Dec 4 - Dec 7 found 15 hours ago Roundtrip flight included Watertown (ART) 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/2025-12-04/2025-12-07/?FromAirport=ART&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=107321604&paandie=true&HotelClass=40&dealMarker=8PL9eVJXftADqLDZ32_5YhcMk9WJZnwIh3tqUO_Wv3XeH4BIinkh6SmUMwhmU92b) ![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 $1,552 per person Nov 14 - Nov 17 found 22 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.4/10 Exceptional! (1,007 reviews) Amazing property!! Worth the price! Reviewed on Oct 13, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-17/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=3981160&paandie=true&HotelClass=40&dealMarker=MotUKBI57nsd6BCPXXeYVx2Us6piApxVnWzVlrAZHSok9o06mgP0xoKUt_Qq1GWy) ![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Portland Harborview Downtown Portland CA $955 per person Dec 4 - Dec 7 found 15 hours ago Roundtrip flight included Watertown (ART) to Portland (PWM) 8.8/10 Excellent! (1,003 reviews) I enjoyed my stay here. Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-07/?FromAirport=ART&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6273&paandie=true&HotelClass=40&dealMarker=slxehwrQ_ERWFZJCZmbwHNjvWjhEyILLoRfIWVv_xvHMmWzmOgCJSK37Bin2okDI) ![Inn By The Sea](https://images.trvl-media.com/lodging/2000000/1550000/1542800/1542725/d0fca35d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Inn By The Sea CA $1,262 per person Dec 4 - Dec 7 found 15 hours ago Roundtrip flight included Watertown (ART) to Portland (PWM) 9.4/10 Exceptional! (281 reviews) Absolutely 5 star. Best bed I’ve slept in at a hotel bar none. Reviewed on Sep 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-07/?FromAirport=ART&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1542725&paandie=true&HotelClass=40&dealMarker=slxehwrQ_ERWFZJCZmbwHNjvWjhEyILLoRfIWVv_xvEc5B9pvGwg1e0ioDyLqwxX) Don't see what you're looking for? See all available trips from Columbus to Great Diamond Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Mountain holidays in Great Diamond Island Price found within the past 48 hours. Click for updated prices. ![White Barn Inn & Spa, Auberge Collection](https://images.trvl-media.com/lodging/1000000/530000/528600/528547/88e57c36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### White Barn Inn & Spa, Auberge Collection CA $1,920 per person Nov 14 - Nov 17 found 22 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.4/10 Exceptional! (102 reviews) The room was extremly small. The front door was hitting the side odf the bad. Reviewed on Sep 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-17/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=528547&paandie=true&HotelClass=50&dealMarker=MotUKBI57nsd6BCPXXeYVx2Us6piApxVnWzVlrAZHSpiqGkgsLBx7Dik-MBQGKKs) Don't see what you're looking for? See all available trips from Columbus to Great Diamond Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Mountain holidays in Great Diamond Island Price found within the past 48 hours. Click for updated prices. ![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 $856 per person Dec 4 - Dec 7 found 15 hours ago Roundtrip flight included Watertown (ART) to Portland (PWM) 9.2/10 Wonderful! (1,581 reviews) This property was pricey. I called beforehand to see if there was self parking and they said no but that was not true. My biggest complaint is that upon check-in, the woman said she wanted to give us a room upgrade, but ultimately was unsuccessful. She really made it seem like we were unfortunately being put in a crappy room. Reviewed on Oct 13, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-07/?FromAirport=ART&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=898621&paandie=true&HotelClass=40&dealMarker=slxehwrQ_ERWFZJCZmbwHNjvWjhEyILLoRfIWVv_xvHS5xnOWCxDa6N7pTxYRkTg) ![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 $979 per person Dec 4 - Dec 7 found 15 hours ago Roundtrip flight included Watertown (ART) 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/2025-12-04/2025-12-07/?FromAirport=ART&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=107321604&paandie=true&HotelClass=40&dealMarker=8PL9eVJXftADqLDZ32_5YhcMk9WJZnwIh3tqUO_Wv3XeH4BIinkh6SmUMwhmU92b) ![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 $1,552 per person Nov 14 - Nov 17 found 22 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.4/10 Exceptional! (1,007 reviews) Amazing property!! Worth the price! Reviewed on Oct 13, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-17/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=3981160&paandie=true&HotelClass=40&dealMarker=MotUKBI57nsd6BCPXXeYVx2Us6piApxVnWzVlrAZHSok9o06mgP0xoKUt_Qq1GWy) Don't see what you're looking for? See all available trips from Columbus to Great Diamond Island [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## More vacations you might like ![](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) ## More Vacations Ideas [Flights to Great Diamond Island](https://expedia.ca/Cheap-Flights-To-Great-Diamond-Island.d6342016.Travel-Guide-Flights)[Great Diamond Island Hotels](https://expedia.ca/Great-Diamond-Island-Hotels.d6342016.Travel-Guide-Hotels)[Great Diamond Island Vacation Rentals](https://expedia.ca/Great-Diamond-Island-Vacation-Rentals.d6342016.Travel-Guide-VacationRentals)[Great Diamond Island Car Rentals](https://expedia.ca/Car-Rentals-In-Great-Diamond-Island.d6342016.Car-Rental-Guide)[Great Diamond Island Vacations](https://expedia.ca/Great-Diamond-Island.d6342016.Destination-Travel-Guides) \* 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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)