Title: Pet-friendly 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 Pet-friendly 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 Pet-friendly 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 $765 per person Dec 21 - Dec 28 just found Roundtrip flight included Toronto (YYZ) to Portland (PWM) 9.2/10 Wonderful! (1,581 reviews) My husband and I visited Maine for our honeymoon and the hotel had a card, meat and cheese board, and a bottle of champagne for us in celebration. Thank you so much! Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-21/2025-12-28/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=898621&paandie=true&HotelClass=40&dealMarker=80Z9HR800k87PdvIsU65awx3k7Dtj3jnBJYxlZQqLrNKa0d0JMsYs5i0hiiVpKyg) ![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 $1,134 per person Nov 21 - Nov 24 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) 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/2025-11-21/2025-11-24/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=107321604&paandie=true&HotelClass=40&dealMarker=6G4VshBxpt1VGdnGDnuoqiusD1bDnrHCMM6GAiX7XKF0A9qGKSnr_YaHJxmxWo9R) ![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 $1,318 per person Nov 21 - Nov 24 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) 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/2025-11-21/2025-11-24/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1542725&paandie=true&HotelClass=40&dealMarker=6G4VshBxpt1VGdnGDnuoqiusD1bDnrHCMM6GAiX7XKFJY9ywVrPdCDIy19Uy6YeH) ![Kennebunkport Captains Collection](https://images.trvl-media.com/lodging/14000000/13280000/13279300/13279259/285f2526_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kennebunkport Captains Collection CA $1,124 per person Nov 21 - Nov 24 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.4/10 Exceptional! (622 reviews) We loved the quietness of the property and how walkable it was to downtown Reviewed on Sep 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-24/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=13279259&paandie=true&HotelClass=40&dealMarker=6G4VshBxpt1VGdnGDnuoqiusD1bDnrHCMM6GAiX7XKELPE0VSeYiYqLUWMwC_uhs) ![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 $1,084 per person Nov 18 - Nov 23 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 8.8/10 Excellent! (1,003 reviews) there was no soap in the shower soap dispenser; shampoo full. a convention was there and they took up almost all of the staff time and efforts. You were a little 2nd tier if you were a tourist couple. Also, pls send me an itemized statement of my bill ; front desk refused to provide one. they told me I had to "go to Expedia". pls send promptly Reviewed on Sep 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-18/2025-11-23/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6273&paandie=true&HotelClass=40&dealMarker=6G4VshBxpt1VGdnGDnuoquxs3R63n4zlf_sokWMjCATSLpl_GdMZLuo6SlKsjM2r) 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/2025-11-03/2025-11-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Pet-friendly 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 $938 per person Nov 21 - Nov 24 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9.2/10 Wonderful! (1,581 reviews) My husband and I visited Maine for our honeymoon and the hotel had a card, meat and cheese board, and a bottle of champagne for us in celebration. Thank you so much! Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-24/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=898621&paandie=true&HotelClass=40&dealMarker=uDaxOxfK0mlPljWbo5JD4INerd2xHfPasJ3uY30jWsavxpAdYgjvk_d4Ck4w1_VQ) ![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 $1,134 per person Nov 21 - Nov 24 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) 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/2025-11-21/2025-11-24/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=107321604&paandie=true&HotelClass=40&dealMarker=6G4VshBxpt1VGdnGDnuoqiusD1bDnrHCMM6GAiX7XKF0A9qGKSnr_YaHJxmxWo9R) ![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 $1,318 per person Nov 21 - Nov 24 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) 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/2025-11-21/2025-11-24/?FromAirport=YYZ&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1542725&paandie=true&HotelClass=40&dealMarker=6G4VshBxpt1VGdnGDnuoqiusD1bDnrHCMM6GAiX7XKFJY9ywVrPdCDIy19Uy6YeH) 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/2025-11-03/2025-11-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Pet-friendly Hotels in Great Diamond Island ![Cozy Coveside Island Retreat](https://images.trvl-media.com/lodging/121000000/120180000/120177500/120177417/6f793f3b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cozy Coveside Island Retreat Portland, ME - 50 min drive from Engine Stay at this vacation home in Portland. Enjoy a fitness center and laundry facilities. Popular attractions Thompson's Point and Little Diamond Island are located ... [](https://expedia.ca/Portland-Hotels-Cozy-Coveside-Island-Retreat.h120177417.Hotel-Information) ![Amazing Ocean View Summer Cottage Rental w/ Boat Mooring on Great Diamond Island](https://images.trvl-media.com/lodging/40000000/39970000/39962500/39962416/3757e94e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Amazing Ocean View Summer Cottage Rental w/ Boat Mooring on Great Diamond Island Great Diamond Island - 50 min drive from Engine Book a stay at this family-friendly vacation home in Portland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Thompson's Point and Little ... Amazing Vacation "This house is a classic Maine island camp. We loved every bit of our stay here. We will be back!!" Reviewed on Aug 31, 2024 [](https://expedia.ca/Portland-Hotels-Great-Ocean-View-Summer-Cottage-Rental-With-Boat-Mooring-On-Great-Diamond-Island.h39962416.Hotel-Information) [See all 2,407 properties in Great Diamond Island](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6342016) 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. ## 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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)