Title: Great Diamond Island Romantic 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 Romantic Vacations ## Book a Romantic Hotel + Flight or Car together to unlock savings ## Top Romantic 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 $865 per person Jun 20 - Jun 23 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Portland (PWM) 9.2/10 Wonderful! (1,776 reviews) Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great. Reviewed on Mar 24, 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 $1,677 per person Jun 3 - Jun 9 found 1 day ago Roundtrip non-stop flight included Phoenix (PHX) to Portland (PWM) 9.4/10 Exceptional! (304 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 ![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 Save 100% on your flight $5,062 per person Jun 3 - Jun 9 found 1 day ago Roundtrip non-stop flight included Phoenix (PHX) 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 ![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 $983 per person May 8 - May 10 found 1 day ago Roundtrip non-stop flight included Minneapolis (MSP) to Portland (PWM) 9.4/10 Exceptional! (1,007 reviews) Gorgeous room in a gorgeous setting. Norman the lead bartender is a treasure. Hector was great as well. Everything was outstanding. Reviewed on Mar 25, 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 Save 100% on your flight $1,417 per person Jun 3 - Jun 9 found 1 day ago Roundtrip non-stop flight included Phoenix (PHX) to Portland (PWM) 9.4/10 Exceptional! (686 reviews) Historic, cozy, and charming mansions and rooms...our stay was amazing. Reviewed on Mar 15, 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/2026-04-28/2026-05-05/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic 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 Save 100% on your flight $5,062 per person Jun 3 - Jun 9 found 1 day ago Roundtrip non-stop flight included Phoenix (PHX) 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/2026-04-28/2026-05-05/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Romantic 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 $486 per person May 8 - May 11 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Portland (PWM) 9.2/10 Wonderful! (1,776 reviews) Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great. Reviewed on Mar 24, 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 Save 100% on your flight $1,460 per person May 10 - May 13 found 1 day ago Roundtrip non-stop flight included Minneapolis (MSP) to Portland (PWM) 9.4/10 Exceptional! (1,007 reviews) Gorgeous room in a gorgeous setting. Norman the lead bartender is a treasure. Hector was great as well. Everything was outstanding. Reviewed on Mar 25, 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 $704 per person May 20 - May 23 found 1 day ago Roundtrip flight included New York (NYC) to Portland (PWM) 9.4/10 Exceptional! (304 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/2026-04-28/2026-05-05/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic 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 $560 per person May 4 - May 8 found 1 day ago Roundtrip flight included Chicago (ORD) 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 $605 per person May 4 - May 8 found 1 day ago Roundtrip flight included Chicago (ORD) to Portland (PWM) 9.2/10 Wonderful! (1,776 reviews) Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great. Reviewed on Mar 24, 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 $647 per person May 4 - May 8 found 1 day ago Roundtrip flight included Chicago (ORD) to Portland (PWM) 9.6/10 Exceptional! (275 reviews) Property is in an excellent location with so much to see and do (and eat) in walking distance. My room was clean, quiet, and well maintained. Staff interaction was minimal (by design) but the few times I spoke with the concierge on site she was pleasant and accommodating. My only negative comment is regarding the toiletry products. I’m a toilet paper snob and that angel soft just doesn’t cut it. Overall I am beyond satisfied with my stay and would absolutely stay here again. Reviewed on Mar 22, 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/2026-04-28/2026-05-05/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## How to find a romantic Great Diamond Island vacation #### How can I find the best Great Diamond Island vacation packages for couples? To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing. #### How can I find cheap Great Diamond Island romantic packages for two? For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering and visiting outside busy months of . #### How can I plan a great romantic trip to Great Diamond Island? Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two. #### How much is a trip for two to Great Diamond Island? Put a price on love with stunning deals for duos starting at just $486\. Stay during the quiet season, in , for breaks to make your bank balance smile. Prices and availability are subject to change. Additional terms may apply. #### Can I book Great Diamond Island spa packages for couples? Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match. #### What’s the best time of year for a romantic vacation in Great Diamond Island? Book your romantic getaway during the quieter months of when you can have the place to yourself, pretty much. To show your partner off to the world, provide a more abundant audience. #### How can I book romantic weekend getaway packages in Great Diamond Island? To book a loved-up break in Great Diamond Island, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation). #### Can I book a romantic trip to Great Diamond Island with free cancellation and/or flexible dates? The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options. #### Why should I book my Great Diamond Island romantic holiday with Expedia? If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection? ## 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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](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.