Title: Great Diamond Island Vacation Packages 2026 from $321 | Expedia.com

[Great Diamond Island Travel Guide](https://expedia.com/Great-Diamond-Island.dx6342016)[Hotels in Great Diamond Island](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)[Flights to Great Diamond Island](https://expedia.com/Cheap-Flights-To-Great-Diamond-Island.d6342016.Travel-Guide-Flights)[Car Rentals in Great Diamond Island](https://expedia.com/Car-Rentals-In-Great-Diamond-Island.d6342016.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6342016/fbb7e9ac-5d97-4416-ad7f-d1a6bdfac217.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Great Diamond Island Vacations from $321

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
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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
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Plan, book, and manage your trip all in one place

## The Latest Great Diamond Island vacation packages

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

$321

per person

May 8 - May 10

found 21 hours ago

Roundtrip flight included

New York (NYC) to Portland (PWM)

9/10 Wonderful! (1,000 reviews)

The room was very clean!

Reviewed on Oct 31, 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

![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 19 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

![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 19 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

![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 21 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

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)

### Discover the most popular places to visit in Great Diamond Island

![State Theatre](https://images.trvl-media.com/place/553248621532668181/12c8418f-9a14-4f93-8c30-2ed80351964b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### State Theatre

4.5/5(88 reviews)

The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.

[](https://expedia.com/State-Theatre-Downtown-Portland.d553248621532668181.Vacation-Attraction)

![Portland Museum of Art](https://images.trvl-media.com/place/6077214/5da73be5-0bbe-40d4-9f90-562d37bd733f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Portland Museum of Art

4.5/5(258 reviews)

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

[](https://expedia.com/Portland-Museum-Of-Art-Downtown-Portland.d6077214.Vacation-Attraction)

![East End Beach](https://images.trvl-media.com/place/6326357/191640a3-578a-49c8-8b3c-7316c332da71.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

[](https://expedia.com/East-End-Beach-East-End.d6326357.Vacation-Attraction)

### What to do in Great Diamond Island

![Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour](https://mediaim.expedia.com/localexpert/44927495/42f8f2e5-289d-480a-a822-cc8751cc6b66.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

$10

per traveler

[](https://expedia.com/things-to-do/downtown-portland-coastal-vibe-and-old-mansions-with-in-add-audio-tour.a44927495.activity-details)

![Portland Self-Guided Driving Audio Tour](https://mediaim.expedia.com/localexpert/45719150/c5757d24-772a-4314-9a5b-385c37350ecc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Portland Smartphone Audio Tour: Self-Guided Drive

$15

per traveler

[](https://expedia.com/things-to-do/portland-smartphone-audio-tour-self-guided-drive.a45719150.activity-details)

![Ultimate Portland Self-Guided Driving GPS Audio Tour](https://mediaim.expedia.com/localexpert/44941422/8edf0b39-e377-40e8-9427-6d82cf3b7f7d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Ultimate Portland Self-Guided Driving GPS Audio Tour

$17

per traveler

**100%** of travellers recommend

[](https://expedia.com/things-to-do/ultimate-portland-self-guided-driving-gps-audio-tour.a44941422.activity-details)

[See all activities in Great Diamond Island](https://expedia.com/things-to-do/search?rid=6342016)

## Great Diamond Island Hotel Deals

![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/c479d2b6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Westin Portland Harborview

157 High St Portland ME

Fully refundableReserve now, pay when you stay

$114 nightly

$126 total

Apr 26 - Apr 27

Total with taxes and fees

8.8/10 Excellent! (1,005 reviews)

I chose this hotel specifically because it was advertised as pet-friendly, as I was traveling with my well-trained dog. While the location was convenient and the room itself was comfortable, the experience was soured by the lack of transparency regarding the pet policy. When I booked, the additional ...

Reviewed on Apr 6, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F26%2F2026&endDate=4%2F27%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true&regionId=6342016)

![Cambria Hotel Portland Downtown-Old Port](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981687/2540bb39_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

$126 nightly

$139 total

Apr 15 - Apr 16

Total with taxes and fees

9.4/10 Exceptional! (1,186 reviews)

Clean, quiet, good stay.

Reviewed on Apr 6, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F15%2F2026&endDate=4%2F16%2F2026&selected=77981687&PinnedHotelID=77981687&HadPinnedHotel=true&regionId=6342016)

![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/1a7f326f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Portland Harbor Hotel

468 Fore Street Portland ME

Fully refundableReserve now, pay when you stay

$165 nightly

$183 total

Apr 12 - Apr 13

Total with taxes and fees

9.2/10 Wonderful! (1,763 reviews)

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

Reviewed on Apr 6, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true&regionId=6342016)

[See all 2,364 properties in Great Diamond Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&regionId=6342016)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

## Find the Best Great Diamond Island Vacation Packages

## Great Diamond Island Essential Information

| Language        | English                              |
| --------------- | ------------------------------------ |
| Currency        | U.S dollars                          |
| Closest Airport | Portland Intl. Jetport Airport (PWM) |

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- [Hotels near East End ](https://www.expedia.com/East-End-Portland-Hotels.0-n553248635975850491-0.Travel-Guide-Filter-Hotels)
- [Hotels near Portland Observatory ](https://www.expedia.com/Portland-Observatory-Hotels.0-l6077226-0.Travel-Guide-Filter-Hotels)
- [Hotels near Southern Maine Community College ](https://www.expedia.com/Southern-Maine-Community-College-Hotels.0-l553248621555471470-0.Travel-Guide-Filter-Hotels)
- [Hotels near Old Port ](https://www.expedia.com/Old-Port-Portland-Hotels.0-n6172121-0.Travel-Guide-Filter-Hotels)
- [Hotels near Willard Beach ](https://www.expedia.com/Willard-Beach-South-Portland-Hotels.0-n643570660110589952-0.Travel-Guide-Filter-Hotels)
- [3 Star Hotels in Willard Beach ](https://www.expedia.com/3Star-Willard-Beach-South-Portland-Hotels.s30-n643570660110589952-0.Travel-Guide-Filter-Hotels)
- [Hotels with Free Airport Shuttle in Portland ](https://www.expedia.com/Portland-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d181420-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels)
- [B&B in Portland ](https://www.expedia.com/Portland-Bed-And-Breakfast.d181420-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Hotels near Willard Beach ](https://www.expedia.com/Willard-Beach-Hotels.0-l6077248-0.Travel-Guide-Filter-Hotels)
- [Hotels near Gilsland Farm Audubon Center ](https://www.expedia.com/Gilsland-Farm-Audubon-Center-Hotels.0-l553248621532668096-0.Travel-Guide-Filter-Hotels)
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- [Flights to Portland ](https://www.expedia.com/Cheap-Flights-To-Portland.d181420.Travel-Guide-Flights)
- [Flights to Peaks Island ](https://www.expedia.com/Cheap-Flights-To-Peaks-Island.d6151240.Travel-Guide-Flights)
- [Flights from Peaks Island ](https://www.expedia.com/lp/flights/6151240/flights-from-peaks-island)
- [Flights to Long Island ](https://www.expedia.com/Cheap-Flights-To-Long-Island.d6046209.Travel-Guide-Flights)
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- [Peaks Island Vacations ](https://www.expedia.com/Peaks-Island.d6151240.Destination-Travel-Guides)
- [Long Island Vacations ](https://www.expedia.com/Long-Island.d6046209.Destination-Travel-Guides)
- [Umbrella Cover Museum ](https://www.expedia.com/Umbrella-Cover-Museum-Peaks-Island.d6326400.Vacation-Attraction)
- [Visit Peaks Island ](https://www.expedia.com/Peaks-Island.dx6151240)
- [Visit Long Island ](https://www.expedia.com/Long-Island.dx6046209)
- [Mackworth Island State Park ](https://www.expedia.com/Mackworth-Island-Falmouth.d6077250.Vacation-Attraction)
- [East End Beach ](https://www.expedia.com/East-End-Beach-East-End.d6326357.Vacation-Attraction)
- [Spring Point Ledge Lighthouse ](https://www.expedia.com/Spring-Point-Ledge-Lighthouse-Maine.d6327870.Vacation-Attraction)
- [Eastern Promenade ](https://www.expedia.com/Eastern-Promenade-East-End.d6326369.Vacation-Attraction)
- [Bug Light ](https://www.expedia.com/Bug-Light-South-Portland.d6077242.Vacation-Attraction)
- [Fort Preble ](https://www.expedia.com/Fort-Preble-South-Portland.d6077244.Vacation-Attraction)
- [South Portland Historical Society Museum ](https://www.expedia.com/South-Portland-Historical-Society-Museum-South-Portland.d6327768.Vacation-Attraction)
- [Maine Narrow Gauge Railroad Company and Museum ](https://www.expedia.com/Maine-Narrow-Gauge-Railroad-Company-And-Museum-Portland.d6327514.Vacation-Attraction)
- [Portland Vacations ](https://www.expedia.com/Portland.d181420.Destination-Travel-Guides)
- [Southern Maine Community College ](https://www.expedia.com/Southern-Maine-Community-College-Willard-Beach.d553248621555471470.Vacation-Attraction)
- [Casco Bay Lines Ferry Terminal ](https://www.expedia.com/Casco-Bay-Lines-Ferry-Terminal-Downtown-Portland.d553248621533120972.Vacation-Attraction)
- [Gilsland Farm Audubon Center ](https://www.expedia.com/Gilsland-Farm-Audubon-Center-Falmouth.d553248621532668096.Vacation-Attraction)
- [Maine Jewish Museum ](https://www.expedia.com/Maine-Jewish-Museum-East-Bayside.d6327496.Vacation-Attraction)
- [Maine Sports Hall of Fame ](https://www.expedia.com/Maine-Sports-Hall-Of-Fame-Downtown-Portland.d553248621532668067.Vacation-Attraction)
- [Lyric Music Theater ](https://www.expedia.com/Lyric-Music-Theater-Ferry-Village.d6326805.Vacation-Attraction)
- [Visit Old Port ](https://www.expedia.com/Portland-Old-Port.dx6172121)
- [N.w. Barrett Gallery ](https://www.expedia.com/NW-Barrett-Gallery-Downtown-Portland.d553248621558114904.Vacation-Attraction)
- [Visit Willard Beach ](https://www.expedia.com/South-Portland-Willard-Beach.dx643570660110589952)
- [Old Port Vacations ](https://www.expedia.com/Old-Port.d6172121.Destination-Travel-Guides)
- [Visit Portland ](https://www.expedia.com/Portland.dx181420)
- [Merrill Auditorium ](https://www.expedia.com/Merrill-Auditorium-Downtown-Portland.d6077222.Vacation-Attraction)
- [Downtown Portland Vacations ](https://www.expedia.com/Downtown-Portland.d6174134.Destination-Travel-Guides)
- [South Portland Vacations ](https://www.expedia.com/South-Portland.d6769.Destination-Travel-Guides)

- [Car rentals near Portland ](https://www.expedia.com/Car-Rentals-In-Portland.d181420.Car-Rental-Guide)
- [Car rentals near Peaks Island ](https://www.expedia.com/Car-Rentals-In-Peaks-Island.d6151240.Car-Rental-Guide)
- [Car rentals near Long Island ](https://www.expedia.com/Car-Rentals-In-Long-Island.d6046209.Car-Rental-Guide)
- [Car rentals near Umbrella Cover Museum ](https://www.expedia.com/Car-Rentals-In-Umbrella-Cover-Museum.d6326400.Car-Rental-Guide)
- [Car rentals near Bug Light ](https://www.expedia.com/Car-Rentals-In-Bug-Light.d6077242.Car-Rental-Guide)
- [Car rentals near Southern Maine Community College ](https://www.expedia.com/Car-Rentals-In-Southern-Maine-Community-College.d553248621555471470.Car-Rental-Guide)

- [Peaks Island Vacation Rentals ](https://www.expedia.com/Peaks-Island-Vacation-Rentals.d6151240.Travel-Guide-VacationRentals)
- [Portland Vacation Rentals ](https://www.expedia.com/Portland-Vacation-Rentals.d181420.Travel-Guide-VacationRentals)

- [Things to do in Portland ](https://www.expedia.com/Things-To-Do-In-Portland.d181420.Travel-Guide-Activities)

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