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

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## Top Cheap vacation packages in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.

![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

$531

per person

May 8 - May 10

found 23 hours 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

![Cliff House Maine](https://images.trvl-media.com/lodging/4000000/3990000/3981200/3981160/50b1cace_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cliff House Maine

Bald Head

Save 100% on your flight

$1,096

per person

May 23 - May 26

found 1 day ago

Roundtrip flight included

New York (NYC) to Portland (PWM)

9.4/10 Exceptional! (1,002 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

![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

$975

per person

Jun 28 - Jul 2

found 21 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

9.2/10 Wonderful! (1,766 reviews)

Staff was amazingly nice and helpful! It will definitely be our favorite hotel in Maine! Thank you guys!

Reviewed on Apr 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

$1,178

per person

Jun 21 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Portland (PWM)

9.4/10 Exceptional! (309 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

![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

$1,081

per person

May 8 - May 10

found 23 hours 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/2026-05-08/2026-05-15/?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

$1,723

per person

Jun 25 - Jun 28

found 22 hours ago

Roundtrip flight included

New York (LGA) 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/2026-05-08/2026-05-15/?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.

![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

$817

per person

Jun 4 - Jun 7

found 11 hours ago

Roundtrip flight included

New York (NYC) to Portland (PWM)

9.4/10 Exceptional! (690 reviews)

Historic, cozy, and charming mansions and rooms...our stay was amazing.

Reviewed on Mar 15, 2026

![Cliff House Maine](https://images.trvl-media.com/lodging/4000000/3990000/3981200/3981160/50b1cace_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cliff House Maine

Bald Head

Save 100% on your flight

$1,096

per person

May 23 - May 26

found 1 day ago

Roundtrip flight included

New York (NYC) to Portland (PWM)

9.4/10 Exceptional! (1,002 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

![Hidden Pond](https://images.trvl-media.com/lodging/26000000/25010000/25007300/25007294/4116a1fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hidden Pond

Save 100% on your flight

$1,525

per person

May 21 - May 24

found 1 day ago

Roundtrip flight included

New York (JFK) to Portland (PWM)

8.6/10 Excellent! (12 reviews)

Exceptionnel cabins, great restaurant, quiet comfortable luxury. Was disappointed by the very high amour of packaging with their food served in plastic containers if you eat by the pool and for all in room dining meals, which is truly excessive and sad to see. I also wish there was a more attractive spa services with steam bath, hot and cold plunge.

Reviewed on Jun 1, 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/2026-05-08/2026-05-15/?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.

![Comfort Inn & Suites Scarborough - Portland](https://images.trvl-media.com/lodging/3000000/2220000/2213300/2213298/019d1b14_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Comfort Inn & Suites Scarborough - Portland

$427

per person

May 22 - May 26

found 1 day ago

Roundtrip flight included

New York (JFK) to Portland (PWM)

7/10 Good! (853 reviews)

We stayed for one night. Place was clean, staff friendly. Pool was small but nice.

Reviewed on Apr 6, 2026

![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

$1,017

per person

May 22 - May 26

found 8 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

9.2/10 Wonderful! (1,766 reviews)

Staff was amazingly nice and helpful! It will definitely be our favorite hotel in Maine! Thank you guys!

Reviewed on Apr 6, 2026

![The McKernan Inn](https://images.trvl-media.com/lodging/106000000/105380000/105370700/105370688/1c19bdab_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The McKernan Inn

$1,042

per person

Jun 28 - Jul 2

found 21 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

9.2/10 Wonderful! (93 reviews)

Beachfront old building labelled "Hospitality" has the best view I have ever seen for breakfast. Watch seals and fishing boats pass by while eating (included with room) continental breakfast freshly prepared just for you. Super private, clean, and well maintained. Feels historic, beach and walking path outside front door. Campus location, has campus security and feels very safe. Kids loved playing on the oceanfront. Makes good base for seeing Portland, but is located in South Portland. Check out the lighthouses!

Reviewed on Apr 7, 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/2026-05-08/2026-05-15/?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 $427, 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. 

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## 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.

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