Title: Great Diamond Island Cheap 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 Cheap Vacations ## Book a Cheap 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 Cheap vacation packages in Great Diamond Island Price found within the past 48 hours. Click for updated prices. ![84 Main ](https://images.trvl-media.com/lodging/8000000/7810000/7805200/7805164/f78a93a3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 84 Main $521 per person Apr 7 - Apr 10 found 1 day ago Roundtrip flight included Washington (DCA) to Portland (PWM) 10/10 Exceptional! (52 reviews) Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities. Reviewed on Dec 29, 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 $717 per person May 18 - May 22 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.2/10 Wonderful! (1,765 reviews) Business facilities were perfect. Front desk man Roman was an all star helping us out. Whole stay was 100/100 Reviewed on Mar 4, 2026 ![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/c479d2b6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Portland Harborview Downtown Portland $605 per person May 18 - May 22 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 8.8/10 Excellent! (1,002 reviews) Very wonderful place; youre welcomed to a very beautiful scene the moment you walk into the doors and the bar at the very top was an amazing sight to see at night especially. Very clean and well kept. The staff were super sweet, service was 10 out of 10\. Sadly didnt get the chance to check out the spa but the food and drinks here are incredible. I hope to come here again in the very near future again and for much longer, very sad to only experience this place for one nighy but so thankful I did. Reviewed on Mar 7, 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 $1,063 per person May 21 - May 24 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.4/10 Exceptional! (300 reviews) Such a beautiful place, great to walk on beach, nice view, staff great.. cozy place.. so well decorated.. highly recommend for a nice quiet get away Reviewed on Mar 4, 2026 ![Kennebunkport Captains Collection](https://images.trvl-media.com/lodging/14000000/13280000/13279300/13279259/c4a328d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kennebunkport Captains Collection $572 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Washington (DCA) to Portland (PWM) 9.4/10 Exceptional! (684 reviews) We absolutely loved our stay with KCC! The room was clean and beautiful. It was nice to have extra amenities such as hot cocoa, water, tea selection, games and even a boutique on site. The breakfast was delicious, fresh! We would definitely recommend this beautiful place to stay, the staff were so friendly and welcoming. Reviewed on Mar 5, 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/2026-04-08/2026-04-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Cheap vacations 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/a7594627_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### White Barn Inn & Spa, Auberge Collection $953 per person May 23 - May 25 found 1 day ago Roundtrip flight included New York (NYC) to Portland (PWM) 9.4/10 Exceptional! (112 reviews) Unbelievable! Amazing Service, and beautiful accommodations. The food was incredible as well! I’ll be back!! Reviewed on Dec 21, 2025 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/2026-04-08/2026-04-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Cheap vacations in Great Diamond Island Price found within the past 48 hours. Click for updated prices. ![84 Main ](https://images.trvl-media.com/lodging/8000000/7810000/7805200/7805164/f78a93a3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 84 Main $521 per person Apr 7 - Apr 10 found 1 day ago Roundtrip flight included Washington (DCA) to Portland (PWM) 10/10 Exceptional! (52 reviews) Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities. Reviewed on Dec 29, 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 $875 per person May 21 - May 24 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.2/10 Wonderful! (1,765 reviews) Business facilities were perfect. Front desk man Roman was an all star helping us out. Whole stay was 100/100 Reviewed on Mar 4, 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 $1,063 per person May 21 - May 24 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.4/10 Exceptional! (300 reviews) Such a beautiful place, great to walk on beach, nice view, staff great.. cozy place.. so well decorated.. highly recommend for a nice quiet get away Reviewed on Mar 4, 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/2026-04-08/2026-04-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Cheap 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 $618 per person May 18 - May 22 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 $717 per person May 18 - May 22 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.2/10 Wonderful! (1,765 reviews) Business facilities were perfect. Front desk man Roman was an all star helping us out. Whole stay was 100/100 Reviewed on Mar 4, 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 $895 per person May 18 - May 22 found 11 hours ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.6/10 Exceptional! (273 reviews) Check-in and check-out are a breeze, easy access to a city parking lot on the block (needed as there was a snow ban on parking when I visited!). In terms of the space itself - clean, well appointed, spacious. Honestly a treat to stay here! Reviewed on Feb 23, 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/2026-04-08/2026-04-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find amazing cheap vacations in Great Diamond Island #### How can I find budget-friendly Great Diamond Island vacation packages on Expedia? Playing around with the easy-to-use search wizard is one of the best ways to find affordable Great Diamond Island vacation packages on Expedia. Tap your dates in and it'll offer some of the cheapest Great Diamond Island getaways within seconds. You can also use the maximum price filter to view deals within your budget. If you're traveling during peak season dates, it's a good idea to book early to snag some of the best offers. You may score irresistible [last-minute specials](https://www.expedia.com/lp/b/vacations/last-minute-deals) for travel in low season. #### How to find cheap last-minute Great Diamond Island travel deals? On Expedia's [last-minute](https://www.expedia.com/lp/b/vacations/last-minute-deals) travel deals page, you'll encounter a plethora of special offers for late vacations to Great Diamond Island. Remember, you're more likely to bag savings on last-minute travel during off-peak periods. Consider checking different departure dates, too. Expedia's nifty search tool lets you compare some of the best last-minute Great Diamond Island vacation packages. The handy filters let you tailor your trip according to your preferences, including hotel star rating, amenities, and property location. #### When is the best time to visit Great Diamond Island on a budget? For some of the cheapest vacation packages to Great Diamond Island from $521, it's best to travel during low season dates. With fewer people traveling during these periods, flights and hotels usually have lower prices. It's also a good idea to avoid popular travel times. These include spring break, Thanksgiving, and other federal holidays. On Expedia, you'll encounter some of the best travel deals to Great Diamond Island. Best of all, vacation [payment plans](https://www.expedia.com/lp/b/vacations/planning) mean you can spread the cost of your trip over 3, 6, or 12 months. #### Can I cancel my Great Diamond Island vacation package booking? Yes, many of Expedia's cheap Great Diamond Island getaway packages allow for free cancellation in case your plans change. Follow the easy steps to cancel by logging into your Expedia account and clicking on “Trips” page'. Keep in mind, though, that each vacation package has different cancellation policies, so be sure to look over them before booking. The good news is you'll clearly see this information on Expedia when you book. There's even a free cancellation search filter that lets you view flexible vacations to Great Diamond Island. #### Why should I book my Great Diamond Island vacation with Expedia? A multitude of exclusive travel deals you won't find anywhere else is one of the top reasons to book your cheap Great Diamond Island vacation package with Expedia. And with one of the widest choices of flights and hotels available, you'll easily find the right trip for you. The handy search wizard and filters let you compare hundreds of great deals in seconds, too. It's not only the cheap prices either: Expedia's booking protection and 24/7 support give you peace of mind before and during your 2026 trip. #### How to find cheap Great Diamond Island vacation packages on Expedia? When searching for budget vacations to Great Diamond Island, look out for the green savings label. This indicates you've snagged a deal only available on Expedia. Another popular way of getting money off your 2026Great Diamond Island vacation is by joining [One Key](https://www.expedia.com/welcome-one-key). Expedia's amazing reward program gives you access to hundreds of member-only discounts on select hotels. Keep a look out for the blue savings label in the search results. Best of all, One Key is free to join. #### Why should I book a package to Great Diamond Island? You'll often snag package savings on your Great Diamond Island vacation when bundling together your flights and accommodation. Expedia even shows you how much you're saving by booking a package. It's not just cheaper prices, either. Packages often have more flexible booking conditions, meaning you're more likely to get a refund in case your 2026 plans change. While booking flights and hotels separately usually requires full payment, Great Diamond Island vacation packages often let you pay a small upfront deposit to confirm. #### How to plan a cheap vacation to Great Diamond Island? Settling on your dates is usually the first step to planning an affordable Great Diamond Island getaway. If you're traveling during peak season dates, it's a good idea to book your trip in advance. This way, you're more likely to bag early-bird deals. Don't rule out a [last-minute travel deal](https://www.expedia.com/lp/b/vacations/last-minute-deals) for low season dates, though. Once you've picked your dates, tap them into the search wizard to see some of the best Great Diamond Island vacation package deals. Hop over to Expedia's [vacation planning page](https://www.expedia.com/lp/b/vacations/planning) for more tips for your dream vacation. ## 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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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