Title: Great Diamond Island Vacation Packages 2026 from $736 | 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 $736

## Book a 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

## The Latest Great Diamond Island vacation packages

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 

$736

per person

Mar 16 - Mar 23

found 1 day ago

Roundtrip flight included

Detroit (DTW) 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

![The McKernan Inn](https://images.trvl-media.com/lodging/106000000/105380000/105370700/105370688/f7ebd781_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The McKernan Inn

$881

per person

Mar 16 - Mar 23

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Portland (PWM)

9/10 Wonderful! (83 reviews)

Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!

Reviewed on Dec 27, 2025

![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Portland Harbor Hotel

Downtown Portland

$808

per person

Mar 16 - Mar 23

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Portland (PWM)

9.2/10 Wonderful! (1,668 reviews)

Really nice room. Tub, separate shower, nice linens.

Reviewed on Feb 7, 2026

![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Portland Regency Hotel & Spa

Downtown Portland

$765

per person

Mar 16 - Mar 23

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Portland (PWM)

9.4/10 Exceptional! (1,512 reviews)

The room we were in was so loud. I think we were near all the plumbing. Didn't sleep well. Hotel was beautiful and the location was amazing.

Reviewed on Jan 30, 2026

![The Docent’s Collection – Thompson Block](https://images.trvl-media.com/lodging/39000000/38780000/38770100/38770068/e5025392_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Docent’s Collection – Thompson Block

Downtown Portland

$889

per person

Mar 16 - Mar 23

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Portland (PWM)

9.6/10 Exceptional! (249 reviews)

Room was very clean, neat vibe, tons of space! Made coming back from

Reviewed on Jan 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/2026-03-08/2026-03-15/?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 showing street scenes as well as an individual femail](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 showing art and interior views as well as a small group of people](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(255 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 which includes general coastal views and a beach as well as a small group of people](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

![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

$17

per traveler

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

![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)

![Ultimate Portland Self-Guided Driving GPS Audio Tour](https://mediaim.expedia.com/localexpert/44941422/00064774-1203-465f-8cee-e200125a2c6a.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

![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Fully refundableReserve now, pay when you stay

$77 nightly

$85 total

Feb 16 - Feb 17

Total with taxes and fees

8/10 Very Good! (1,351 reviews)

Great location great staff everything functioned.

Reviewed on Feb 6, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F16%2F2026&endDate=2%2F17%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true&regionId=6342016)

![Long Creek Hotel by IHG](https://images.trvl-media.com/lodging/1000000/30000/24300/24280/f3b41288_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Long Creek Hotel by IHG

171 Philbrook Ave South Portland ME

Fully refundable

$83 nightly

$90 total

Feb 11 - Feb 12

Total with taxes and fees

7.4/10 Good! (1,001 reviews)

Room was clean, bed was large and comfortable, staff was friendly. Sadly however, The pool and hot tub were closed.

Reviewed on Feb 2, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F11%2F2026&endDate=2%2F12%2F2026&selected=24280&PinnedHotelID=24280&HadPinnedHotel=true&regionId=6342016)

![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Portland Harbor Hotel

468 Fore Street Portland ME

Fully refundableReserve now, pay when you stay

$147 nightly

$163 total

Feb 11 - Feb 12

Total with taxes and fees

9.2/10 Wonderful! (1,751 reviews)

Wonderful stay!

Reviewed on Feb 7, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F11%2F2026&endDate=2%2F12%2F2026&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true&regionId=6342016)

[See all 2,265 properties in Great Diamond Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F9%2F2026&endDate=2%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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- [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)
- [Pet-friendly Hotels in Portland ](https://www.expedia.com/Portland-Hotels-Pet-Friendly-Hotel.0-0-d181420-tPetfriendlyHotel.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)
- [Flights from Portland Intl. Jetport ](https://www.expedia.com/lp/airports/pwm/flights-from-portland-intl-jetport-airport)

- [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 ](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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