Title: Great Diamond Island Vacation Packages 2026 from $669 | 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 $669

## 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 

Save 100% on your flight

$669

per person

Apr 13 - Apr 19

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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

![Cliff House Maine](https://images.trvl-media.com/lodging/4000000/3990000/3981200/3981160/eb122fc0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cliff House Maine

Bald Head

Save 100% on your flight

$1,513

per person

Apr 20 - Apr 26

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Portland (PWM)

9.4/10 Exceptional! (1,001 reviews)

Went for our honeymoon and fell in love with this place! Will definitely go back!

Reviewed on Feb 26, 2026

![The Weldon Hotel](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/38875013_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Weldon Hotel

Downtown Portland

$716

per person

May 9 - May 12

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Portland (PWM)

9.8/10 Exceptional! (86 reviews)

Location is excellent. Short walking distance to every good restaurant and shop. The property was very nice and clean. The kitchen is very well equipped. The gym is very good sized for the size of the apartment building with 13 units in it. The management’s communication was prompt and friendly and responded to all of our wishes. However, the place is advertised as a hotel, but don’t expect services as in a hotel. It resembles more a short term rental home - no cleaning service and no lobby. Otherwise everything was very nice in the apartment and we had a great time.

Reviewed on Jan 3, 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

$811

per person

May 9 - May 12

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Portland (PWM)

9.6/10 Exceptional! (249 reviews)

Check-in and check-out are a breeze, easy access to a city parking lot on the block (needed as there was a snow ban on parking when I visited!). In terms of the space itself - clean, well appointed, spacious. Honestly a treat to stay here!

Reviewed on Feb 23, 2026

![Blind Tiger Portland - Danforth Street.](https://images.trvl-media.com/lodging/1000000/210000/200300/200246/4e66cf6e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Blind Tiger Portland - Danforth Street.

West End

$891

per person

May 9 - May 12

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Portland (PWM)

9.6/10 Exceptional! (161 reviews)

The whole was cozy! Well curated style and knowledgeable staff.

Reviewed on Jan 5, 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/2026-03-27/2026-04-03/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_6342016)

### 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)

![Spring Point Ledge Lighthouse is the only caisson-style light station in the USA that visitors can walk to. Located on the breakwater at Southern Maine Community College in South Portland.](https://images.trvl-media.com/place/6077216/66b598f5-9cf2-462e-8d29-6ce35cd28e10.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### University of Southern Maine

4/5(102 reviews)

Explore the campus of University of Southern Maine during your stay in Portland. Stroll along the seaside or attend a sporting event in the area. 

[](https://expedia.com/University-Of-Southern-Maine-Oakdale.d6077216.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

![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Westin Portland Harborview

157 High St Portland ME

Fully refundableReserve now, pay when you stay

$98 nightly

$108 total

Mar 15 - Mar 16

Total with taxes and fees

8.8/10 Excellent! (1,002 reviews)

Parking to hotel was was very poor , trash overflowing waterlogged elevators , felt unsafe. Visited the restaurant on top floor waited 15 minutes to be acknowledged and left , not that busy staff not interested - very very poor. Front desk failed to activate parking causing me to be stuck at gate ...

Reviewed on Feb 26, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true&regionId=6342016)

![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

Mar 5 - Mar 6

Total with taxes and fees

8/10 Very Good! (1,378 reviews)

The room was very clean, and the staff was very friendly. The only thing that was disappointing was that when we got ready, and went to use the hot tub it was cold.

Reviewed on Feb 26, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F5%2F2026&endDate=3%2F6%2F2026&selected=7171&PinnedHotelID=7171&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

$156 nightly

$173 total

Mar 1 - Mar 2

Total with taxes and fees

9.2/10 Wonderful! (1,777 reviews)

Location was great, staff was friendly (especially adam at the front desk) but the bed was very uncomfortable, pillows were cheap and deflated, and the whole "resort fee" was very offputting. I would rather just be told a real rate when I book over getting an extra few hundred in charges. The 35$ ...

Reviewed on Feb 23, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true&regionId=6342016)

[See all 2,264 properties in Great Diamond Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F28%2F2026&endDate=3%2F1%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 Maine Narrow Gauge Railroad Company and Museum ](https://www.expedia.com/Maine-Narrow-Gauge-Railroad-Company-And-Museum-Hotels.0-l6327514-0.Travel-Guide-Filter-Hotels)
- [Hotels near Munjoy Hill ](https://www.expedia.com/Munjoy-Hill-Portland-Hotels.0-n553248635976477266-0.Travel-Guide-Filter-Hotels)
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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)
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- [B&B in Portland ](https://www.expedia.com/Portland-Bed-And-Breakfast.d181420-aaBedAndBreakfast.Travel-Guide-Accommodation)
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- [Flights to Peaks Island ](https://www.expedia.com/Cheap-Flights-To-Peaks-Island.d6151240.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)
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- [Mackworth Island State Park ](https://www.expedia.com/Mackworth-Island-Falmouth.d6077250.Vacation-Attraction)
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- [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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