Title: Great Diamond Island Mountain Vacations 2026/2027 | 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 Mountain Vacations and Getaways ## Book a Mountain 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 Mountain vacation packages in Great Diamond Island Price found within the past 48 hours. Click for updated prices. ![HomeAwhile](https://images.trvl-media.com/lodging/121000000/120690000/120687300/120687259/72fd64d9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### HomeAwhile $283 per person May 22 - May 25 found 1 day ago Roundtrip flight included New York (JFK) to Portland (PWM) No reviews ![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 $618 per person May 22 - May 25 found 1 day ago Roundtrip flight included New York (JFK) to Portland (PWM) 9.2/10 Wonderful! (1,766 reviews) Very convenient. Helpful staff. The room was very small and not a great space for relaxing. Reviewed on Mar 8, 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 $1,503 per person Apr 19 - Apr 24 found 1 day ago Roundtrip flight included Minneapolis (MSP) to Portland (PWM) 9.4/10 Exceptional! (1,005 reviews) Great hotel with super nice views! Reviewed on Mar 1, 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 Save 100% on your flight $611 per person May 8 - May 11 found 1 day ago Roundtrip flight included New York (NYC) 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 ![The Weldon Hotel](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/9fd24e5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Weldon Hotel Downtown Portland Save 100% on your flight $880 per person May 22 - May 25 found 1 day ago Roundtrip flight included New York (JFK) to Portland (PWM) 9.8/10 Exceptional! (93 reviews) Clean and comfortable. The gym was great. Reviewed on Mar 6, 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/2026-04-11/2026-04-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Mountain 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 $1,264 per person May 8 - May 11 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/2026-04-11/2026-04-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Mountain vacations in Great Diamond Island Price found within the past 48 hours. Click for updated prices. ![HomeAwhile](https://images.trvl-media.com/lodging/121000000/120690000/120687300/120687259/72fd64d9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### HomeAwhile $283 per person May 22 - May 25 found 1 day ago Roundtrip flight included New York (JFK) to Portland (PWM) No reviews ![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 $618 per person May 22 - May 25 found 1 day ago Roundtrip flight included New York (JFK) to Portland (PWM) 9.2/10 Wonderful! (1,766 reviews) Very convenient. Helpful staff. The room was very small and not a great space for relaxing. Reviewed on Mar 8, 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 $955 per person May 8 - May 11 found 1 day ago Roundtrip flight included New York (NYC) to Portland (PWM) 9.4/10 Exceptional! (1,005 reviews) Great hotel with super nice views! Reviewed on Mar 1, 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/2026-04-11/2026-04-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Mountain 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 $711 per person May 31 - Jun 4 found 12 hours ago Roundtrip flight included Minneapolis (MSP) to Portland (PWM) 9.2/10 Wonderful! (1,766 reviews) Very convenient. Helpful staff. The room was very small and not a great space for relaxing. Reviewed on Mar 8, 2026 ![The Weldon Hotel](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/9fd24e5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Weldon Hotel Downtown Portland Save 100% on your flight $814 per person May 31 - Jun 4 found 12 hours ago Roundtrip flight included Minneapolis (MSP) to Portland (PWM) 9.8/10 Exceptional! (93 reviews) Clean and comfortable. The gym was great. Reviewed on Mar 6, 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 $838 per person May 18 - May 22 found 1 day ago Roundtrip flight included New York (NYC) to Portland (PWM) 9.4/10 Exceptional! (302 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/2026-04-11/2026-04-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find amazing mountains vacations in Great Diamond Island #### How to plan for a mountain vacation in Great Diamond Island? The first step to planning your mountain vacation to Great Diamond Island is to decide what dates you want to go. In the winter months, fresh snowfall means you could hit the slopes at ski resorts near Great Diamond Island, while summer invites you to enjoy scenic hikes. It's a good idea to choose the type of accommodation you'd prefer, too. On Expedia, you'll encounter a vast array of options in Great Diamond Island, from famous chain hotels to charming cabins. The [vacation planning page](https://www.expedia.com/lp/b/vacations/planning) has more tips for organizing your Great Diamond Island mountain vacation. #### What amenities should I look for when booking a mountain resort in Great Diamond Island? When booking accommodation for your mountain vacation to Great Diamond Island, check to see if where you're staying has heating. Great Diamond Island's mountain air means it can feel fresh at night. If you're craving a special stay, look to see if the hotel offers mountain view rooms, or has a pool or hot tub to unwind in the evenings. Expedia's handy search filters include all these amenities and more, making it a breeze to book the right place to stay on your Great Diamond Island vacation package. #### Why should I choose a package for my mountain vacation in Great Diamond Island? Choosing a package for your Great Diamond Island vacation often works out cheaper thanks to the savings you get for bundling up your flights and hotel. You'll typically find it costs more when booking these separately. On Expedia, the green label even shows you how much you're saving. Packages also tend to be more flexible, meaning it's more likely you can cancel for free in case your 2026 plans change. You can usually secure your package by paying a small upfront deposit, whereas booking flights separately requires full payment. #### What does a Great Diamond Island package typically include? Return flight tickets, your accommodation, and applicable taxes are typically included when you book a mountain vacation package to Great Diamond Island from $283\. Hotels may include breakfast and Wi-Fi, while the airfare may include checked luggage. Certain resorts may even include ski passes. As each Great Diamond Island vacation package is different, be sure to double-check what's included before you confirm. If you want a hassle-free trip, consider booking Great Diamond Island all-inclusive vacation packages as these include all meals. #### How can I book my Great Diamond Island on Expedia? Comparing some of the best deals using the search wizard is one of the first steps to booking your Great Diamond Island mountain vacation on Expedia. Take advantage of the search filters to narrow down hundreds of options at the click of a button. If you've got a strict budget, use the maximum price filter to set your limit. When you've pinned down your Great Diamond Island package vacation, book it in just a few clicks. You'll also have the option to spread the cost with Expedia's [payment plans](https://www.expedia.com/lp/b/vacations/payment-plans). #### Why book your Great Diamond Island mountain vacation with Expedia? With meaty exclusive deals you won't find anywhere else, you'll keep more cash in your pocket when booking your Great Diamond Island vacation package on Expedia. No matter your preferences or tastes, you'll find the right place to stay thanks to the wide selection of accommodation. There are even last-minute deals, too. And if that's not enough, join One Key for free. Expedia's reward program lets you earn points on eligible trips and also gives you access to juicy member-only discounts. #### Can I cancel my mountain vacation package booking? Yes, as most of Expedia's mountain vacation packages to Great Diamond Island are flexible, you can often cancel for free. Doing so is easy, too—log in to the “Trips” section and follow the steps. Don't forget to double-check the cancellation policy before booking, as not all Great Diamond Island vacation packages are flexible. The good news is Expedia will display this to you before payment. Take advantage of the free cancellation search filter so you'll be able to narrow down your search to view only flexible Great Diamond Island vacation packages. #### What types of mountain accommodations are available in Great Diamond Island? 5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to Great Diamond Island. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation. ## 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 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](https://www.expedia.com/lp/theme-vacations/mountain-vacations/205/Arkansas) > - [Kentucky Mountain Vacations ](https://www.expedia.com/lp/theme-vacations/mountain-vacations/219/Kentucky) > - [United States of America Mountain Vacations ](https://www.expedia.com/lp/theme-vacations/mountain-vacations/201/United-States-of-America) > - [South Carolina Mountain Vacations ](https://www.expedia.com/lp/theme-vacations/mountain-vacations/242/South-Carolina) > - [Iron Mountain Vacations ](https://www.expedia.com/lp/theme-vacations/mountain-vacations/553248634539843305/Iron) > - [Alabama Mountain Vacations ](https://www.expedia.com/lp/theme-vacations/mountain-vacations/202/Alabama) > - [Buffalo Mountain Vacations ](https://www.expedia.com/lp/theme-vacations/mountain-vacations/3000405545/Buffalo) > - [West Virginia Mountain Vacations ](https://www.expedia.com/lp/theme-vacations/mountain-vacations/250/West-Virginia) ## More 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