Title: Great Diamond Island Kid friendly Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/6342016/fbb7e9ac-5d97-4416-ad7f-d1a6bdfac217.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Great Diamond Island Kid friendly Vacations ## Book a Kid friendly Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 Kid friendly vacation packages in Great Diamond Island Price found within the past 48 hours. Click for updated prices. ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/1a7f326f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Harbor Hotel Downtown Portland Save 100% on your flight $644 per person May 7 - May 11 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.2/10 Wonderful! (1,776 reviews) We could have moved right in and been happy for life. Flawless. Reviewed on Mar 30, 2026 ![Inn By The Sea](https://images.trvl-media.com/lodging/2000000/1550000/1542800/1542725/a8100548_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Inn By The Sea Save 100% on your flight $1,986 per person Jun 22 - Jun 26 found 22 hours ago Roundtrip flight included San Francisco (SFO) to Portland (PWM) 9.4/10 Exceptional! (304 reviews) This was my first trip away since having kids 12 years ago. The staff was very friendly, helpful and attentive. The parking lot, lobby, halls and room were very clean. Our dinner and breakfast at the Inn were absolutely delicious. The ingredients were fresh and the flavors complimented each other well. It was difficult to make a choice on what to order. We didn't have a pet with us but did see several dogs during dining and were impressed with dog menu. I would highly recommend to anyone to stay at the Inn and if you are unable to at least have a meal in the restaurant. We are already planning a longer stay next time. Reviewed on Mar 30, 2026 ![Cliff House Maine](https://images.trvl-media.com/lodging/4000000/3990000/3981200/3981160/fe5a854b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cliff House Maine Bald Head $1,209 per person May 7 - May 10 found 1 day ago Roundtrip non-stop flight included Minneapolis (MSP) to Portland (PWM) 9.4/10 Exceptional! (1,007 reviews) The property is amazing and the staff were polite and very attentive. It’s a negative for me that I couldn’t take my 8 year old in the outdoor pool, but I’m sure if i wasn’t there with a child I’d appreciate a kid-free zone. The indoor pool was pretty filthy, with some wrappers and things floating in the water. The room service food was surprisingly just okay, with watery omelettes, minimalist potatoes for breakfast, a namesake pork sandwich that leaned toward a Cuban but took a left hand toward a crockpot pork. The chefs plate charcuterie was fine except for some form of pate that appeared as if the chef had chewed up some prosciutto , formed it into a rectangle, and pressed two pistachio bits it. I figured it for a nasty kitchen prank on the wealthy snobs paying $35 for a lunch able, so I left it behind. I can’t lie — the whole milk from a local farm that was supplied on each floor’s coffee bar was the best milk I’ve ever tasted in my life. I literally skipped the coffee and drank the milk by the glass, this cannot be overstated as trivial as it seems. Reviewed on Mar 31, 2026 ![Grasshopper Inn](https://images.trvl-media.com/lodging/93000000/92430000/92420700/92420655/93f79b4a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Grasshopper Inn $1,103 per person May 29 - Jun 1 found 1 day ago Roundtrip non-stop flight included Minneapolis (MSP) to Portland (PWM) 9.8/10 Exceptional! (71 reviews) We had a fantastic stay at Grasshopper Inn and will definitely return when back in the area. Clean, friendly staff and brilliant location. Reviewed on Oct 22, 2025 ![HomeAwhile](https://images.trvl-media.com/lodging/121000000/120690000/120687300/120687259/72fd64d9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### HomeAwhile $667 per person Jun 19 - Jun 23 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) No reviews Pros:The rooms were immaculate! Full size fridge, microwave, dishwasher, dishes , utensils etc! Nice livingroom area. Cons: it's contactless but thankfully there was someone at the desk. We got our key cards but they didn't work so luckily she could fix them. I never got the email the last night with directions to check out as promised. But we figured it out. Reviewed on Mar 28, 2026 Don't see what you're looking for? See all available trips from Columbus to Great Diamond Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-01/2026-05-08/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Kid friendly vacations in Great Diamond Island Price found within the past 48 hours. Click for updated prices. ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/1a7f326f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Harbor Hotel Downtown Portland Save 100% on your flight $1,100 per person Jun 18 - Jun 21 found 19 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Portland (PWM) 9.2/10 Wonderful! (1,776 reviews) We could have moved right in and been happy for life. Flawless. Reviewed on Mar 30, 2026 ![Cliff House Maine](https://images.trvl-media.com/lodging/4000000/3990000/3981200/3981160/fe5a854b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cliff House Maine Bald Head $1,209 per person May 7 - May 10 found 1 day ago Roundtrip non-stop flight included Minneapolis (MSP) to Portland (PWM) 9.4/10 Exceptional! (1,007 reviews) The property is amazing and the staff were polite and very attentive. It’s a negative for me that I couldn’t take my 8 year old in the outdoor pool, but I’m sure if i wasn’t there with a child I’d appreciate a kid-free zone. The indoor pool was pretty filthy, with some wrappers and things floating in the water. The room service food was surprisingly just okay, with watery omelettes, minimalist potatoes for breakfast, a namesake pork sandwich that leaned toward a Cuban but took a left hand toward a crockpot pork. The chefs plate charcuterie was fine except for some form of pate that appeared as if the chef had chewed up some prosciutto , formed it into a rectangle, and pressed two pistachio bits it. I figured it for a nasty kitchen prank on the wealthy snobs paying $35 for a lunch able, so I left it behind. I can’t lie — the whole milk from a local farm that was supplied on each floor’s coffee bar was the best milk I’ve ever tasted in my life. I literally skipped the coffee and drank the milk by the glass, this cannot be overstated as trivial as it seems. Reviewed on Mar 31, 2026 ![Canopy by Hilton Portland Waterfront](https://images.trvl-media.com/lodging/65000000/64480000/64474900/64474828/419cdab1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Canopy by Hilton Portland Waterfront Downtown Portland $1,191 per person Jun 4 - Jun 7 found 23 hours ago Roundtrip non-stop flight included Minneapolis (MSP) to Portland (PWM) 9.4/10 Exceptional! (1,007 reviews) Nice room, staff was very nice and welcoming. Nice bar area Reviewed on Mar 26, 2026 Don't see what you're looking for? See all available trips from Columbus to Great Diamond Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-01/2026-05-08/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Kid friendly vacations in Great Diamond Island 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 $538 per person May 7 - May 11 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) 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 Save 100% on your flight $644 per person May 7 - May 11 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.2/10 Wonderful! (1,776 reviews) We could have moved right in and been happy for life. Flawless. Reviewed on Mar 30, 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 Save 100% on your flight $786 per person May 7 - May 11 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.6/10 Exceptional! (275 reviews) So spacious, decor is modern yet warm. Staff super friendly and helpful. Perfect location for concerts at Merrill, short walk. Reviewed on Mar 28, 2026 Don't see what you're looking for? See all available trips from Columbus to Great Diamond Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-01/2026-05-08/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## FAQs: family vacation packages in Great Diamond Island #### How can I find the best family vacation packages in Great Diamond Island? For fam-tastic vacation packages in Great Diamond Island, check the family-friendly filter and add child-charming amenities, like water parks and pools. Read reviews written by other broods to be sure your chosen stay packs plenty of rest and play. #### How can I book family-friendly vacations in Great Diamond Island on a budget? For family- and wallet-friendly trips, filter your search results by budget. You can also sort by price. When bringing the whole brigade on a budget, consider staying in low season or outside the city or. To save more coin, accommodation with a kitchen can be your friend—a bowl of pasta at home is always cheaper than feeding the team at a restaurant. #### What does a family trip to Great Diamond Island cost? You could book your amazing family trip to Great Diamond Island just $538\. But with so many brilliant breaks on offer, there’s something for every wallet. Prices and availability are subject to change. Additional terms may apply. #### Can I book an all-inclusive Great Diamond Island family vacation package? Check the all-inclusive filter for an all-you-could-ever-wish-for family vacay. Click more of your favorite filters for even more extravagance. Perhaps an ocean view, spa, or hot tub. Maybe a water park, epic kids club, or activities galore. #### How can I plan a fun family vacation in Great Diamond Island? Search for stays with kid-satisfying extras, like water parks, and teenage-friendly free Wi-Fi, so they can post about all their vacation adventures for all their buddies back home. Book up local attractions, excursions, and experiences—and they might even put their phone down for a few minutes. #### How can I find Great Diamond Island family vacation deals? Delightful deals often dwell outside high season, so move your travel dates around for top deals. You can also book up a little away from the major Great Diamond Island landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains. #### Can I book a Great Diamond Island family vacation package with free cancellation and/or flexible dates? Free cancellation makes for a hassle-free family vacation. Filter by payment option to find fully flexible trips, including buy now, pay later options. #### Why should I book my Great Diamond Island family trip with Expedia? You can easily find fun for all the family with the super-handy filters. It’s easy to build your dream kid-friendly vacation in just a few clicks. And you can bundle your accommodation, airfare, and car rental in just a few more. ## 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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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Vacation Ideas [Flights to Great Diamond Island ](https://expedia.com/Cheap-Flights-To-Great-Diamond-Island.d6342016.Travel-Guide-Flights)[ Great Diamond Island Hotels ](https://expedia.com/Great-Diamond-Island-Hotels.d6342016.Travel-Guide-Hotels)[ Vacation Rentals in Great Diamond Island ](https://expedia.com/Great-Diamond-Island-Vacation-Rentals.d6342016.Travel-Guide-VacationRentals)[ Car Rentals in Great Diamond Island ](https://expedia.com/Car-Rentals-In-Great-Diamond-Island.d6342016.Car-Rental-Guide)[ Great Diamond Island Vacations ](https://expedia.com/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 even more - get up to 20% on select hotels 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