Title: Great Island Vacation Packages 2026 from $760 | Expedia.com

[Great Island Travel Guide](https://expedia.com/Great-Island.dx553248635976193455)[Hotels in Great Island](https://expedia.com/Great-Island-Hotels.d553248635976193455.Travel-Guide-Hotels)[Vacation Rentals in Great Island](https://expedia.com/Great-Island-Vacation-Rentals.d553248635976193455.Travel-Guide-VacationRentals)[Flights to Great Island](https://expedia.com/Cheap-Flights-To-Great-Island.d553248635976193455.Travel-Guide-Flights)[Car Rentals in Great Island](https://expedia.com/Car-Rentals-In-Great-Island.d553248635976193455.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248635976193455/b810478a-1b10-4d3d-875c-106512d8fc7d.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Great Island Vacations from $760

## 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 Island vacation packages

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

$760

per person

May 11 - May 16

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Portland (PWM)

9.2/10 Wonderful! (1,776 reviews)

Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great.

Reviewed on Mar 24, 2026

![The Docent's Collection at 121 Middle Street](https://images.trvl-media.com/lodging/39000000/38780000/38770100/38770068/148140d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Docent's Collection at 121 Middle Street

Downtown Portland

Save 100% on your flight

$803

per person

May 11 - May 16

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Portland (PWM)

9.6/10 Exceptional! (275 reviews)

Property is in an excellent location with so much to see and do (and eat) in walking distance. My room was clean, quiet, and well maintained. Staff interaction was minimal (by design) but the few times I spoke with the concierge on site she was pleasant and accommodating. My only negative comment is regarding the toiletry products. I’m a toilet paper snob and that angel soft just doesn’t cut it. Overall I am beyond satisfied with my stay and would absolutely stay here again.

Reviewed on Mar 22, 2026

![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

$803

per person

May 5 - May 11

found 16 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Portland (PWM)

9/10 Wonderful! (1,000 reviews)

The room was very clean!

Reviewed on Oct 31, 2025

![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

$1,249

per person

Jun 16 - Jun 20

found 9 hours ago

Roundtrip non-stop flight included

Chicago (CHI) to Portland (PWM)

9.4/10 Exceptional! (304 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

![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

$1,491

per person

Jun 4 - Jun 7

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Portland (PWM)

9.4/10 Exceptional! (1,007 reviews)

Check in was smooth and set the tone for a relaxed upscale experience. Valet available and doorman took our bags to the room. Room was great, beautiful ocean view, soft and silky sheets/down bedding. Pool and hot tub were amazing. Was so beautiful and peaceful hearing the waves crash against the rocks. Well worth it!

Reviewed on Mar 24, 2026

Don't see what you're looking for?

See all available trips from Columbus to Great Island

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-25/2026-05-02/?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 Island

#### Bailey Island Bridge

4.5/5(9 reviews)

Find out about the history of Bailey Island when you spend time at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails. 

[](https://expedia.com/Bailey-Island-Bridge-Bailey-Island.d6077256.Vacation-Attraction)

#### Land's End Gift Shop

Enjoy an outing to Land's End Gift Shop during your stay in Bailey Island. While you're in the area, find time to visit its shops. 

[](https://expedia.com/Lands-End-Gift-Shop-Bailey-Island.d553248621532668102.Vacation-Attraction)

#### Cobwork Bridge

You can find out about the history of Bailey Island when you stop by Cobwork Bridge. Stroll along the seaside or seek out the hiking trails. 

[](https://expedia.com/Cobwork-Bridge-Bailey-Island.d553248621532668105.Vacation-Attraction)

## Great 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

$98 nightly

$108 total

Apr 12 - Apr 13

Total with taxes and fees

8.8/10 Excellent! (1,003 reviews)

The staff was very helpful. Breakfast was included. Full service, not continental. Really good food. Parking was validated. No surprises on put bill. Definitely recommended.

Reviewed on Mar 22, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true&regionId=553248635976193455)

![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/c90266f6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Fully refundable

$77 nightly

$85 total

Apr 13 - Apr 14

Total with taxes and fees

8/10 Very Good! (1,404 reviews)

Clean room , nice pool area and quiet ,will say that the beds are kinda uncomfortable but if you’re there for a night it’s not too bad ! I’d come back again.

Reviewed on Mar 22, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F13%2F2026&endDate=4%2F14%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true&regionId=553248635976193455)

![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

$161 nightly

$178 total

Apr 5 - Apr 6

Total with taxes and fees

9.2/10 Wonderful! (1,774 reviews)

Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great.

Reviewed on Mar 24, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true&regionId=553248635976193455)

[See all 2,072 properties in Great Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F26%2F2026&endDate=3%2F27%2F2026&regionId=553248635976193455)

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 Island Vacation Packages

## Great Island Essential Information

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

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- [4 Star Hotels in Hermit Island ](https://www.expedia.com/4Star-Hermit-Island-Hotels.s40-0-d6341836.Travel-Guide-Filter-Hotels)
- [B&B in Hermit Island ](https://www.expedia.com/Hermit-Island-Bed-And-Breakfast.d6341836-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [3 Star Hotels in Hermit Island ](https://www.expedia.com/3Star-Hermit-Island-Hotels.s30-0-d6341836.Travel-Guide-Filter-Hotels)

- [Flights to Orrs Island ](https://www.expedia.com/Cheap-Flights-To-Orrs-Island.d3000440072.Travel-Guide-Flights)
- [Flights to Harpswell ](https://www.expedia.com/Cheap-Flights-To-Harpswell.d553248635077688915.Travel-Guide-Flights)
- [Flights to Cundys Harbor ](https://www.expedia.com/Cheap-Flights-To-Cundys-Harbor.d3000439764.Travel-Guide-Flights)
- [Flights to Bailey Island ](https://www.expedia.com/Cheap-Flights-To-Bailey-Island.d6046825.Travel-Guide-Flights)
- [Flights to Sebasco Estates ](https://www.expedia.com/Cheap-Flights-To-Sebasco-Estates.d180774.Travel-Guide-Flights)
- [Flights from Hermit Island ](https://www.expedia.com/lp/flights/6341836/flights-from-hermit-island)

- [Visit Orrs Island ](https://www.expedia.com/Orrs-Island.dx3000440072)
- [Paddleworks ](https://www.expedia.com/Paddleworks-Orrs-Island.d553248621532668107.Vacation-Attraction)
- [Cundys Harbor Vacations ](https://www.expedia.com/Cundys-Harbor.d3000439764.Destination-Travel-Guides)
- [Visit Harpswell ](https://www.expedia.com/Harpswell.dx553248635077688915)
- [Bailey Island Bridge ](https://www.expedia.com/Bailey-Island-Bridge-Bailey-Island.d6077256.Vacation-Attraction)
- [Visit Cundys Harbor ](https://www.expedia.com/Cundys-Harbor.dx3000439764)
- [Ash Cove Pottery ](https://www.expedia.com/Ash-Cove-Pottery-Harpswell.d553248621532668104.Vacation-Attraction)
- [Visit Bailey Island ](https://www.expedia.com/Bailey-Island.dx6046825)
- [Bailey Island Vacations ](https://www.expedia.com/Bailey-Island.d6046825.Destination-Travel-Guides)
- [Sebasco Estates Vacations ](https://www.expedia.com/Sebasco-Estates.d180774.Destination-Travel-Guides)
- [Visit Sebascodegan Island ](https://www.expedia.com/Sebascodegan-Island.dx553248635975859087)
- [Visit Sebasco Estates ](https://www.expedia.com/Sebasco-Estates.dx180774)
- [Land's End Gift Shop ](https://www.expedia.com/Lands-End-Gift-Shop-Bailey-Island.d553248621532668102.Vacation-Attraction)
- [Hermit Island Vacations ](https://www.expedia.com/Hermit-Island.d6341836.Destination-Travel-Guides)
- [Visit Hermit Island ](https://www.expedia.com/Hermit-Island.dx6341836)

- [Car rentals near Orrs Island ](https://www.expedia.com/Car-Rentals-In-Orrs-Island.d3000440072.Car-Rental-Guide)
- [Car rentals near Harpswell Center ](https://www.expedia.com/Car-Rentals-In-Harpswell-Center.d553248635975848499.Car-Rental-Guide)
- [Car rentals near Harpswell ](https://www.expedia.com/Car-Rentals-In-Harpswell.d553248635077688915.Car-Rental-Guide)
- [Island Car Rentals Rental Cars in Harpswell ](https://www.expedia.com/Island-Car-Rentals-Car-Rentals-In-Harpswell.d553248635077688915-c1132.Car-Rental-Guide-Suppliers)
- [Convertible Car Rentals in Harpswell ](https://www.expedia.com/Convertible-Car-Rentals-In-Harpswell.d553248635077688915-tConvertible.Car-Rental-Guide-Class)
- [Avis Canaries Rental Cars in Harpswell ](https://www.expedia.com/Avis-Canaries-Car-Rentals-In-Harpswell.d553248635077688915-c1135.Car-Rental-Guide-Suppliers)
- [Car rentals near Cundys Harbor ](https://www.expedia.com/Car-Rentals-In-Cundys-Harbor.d3000439764.Car-Rental-Guide)
- [Car rentals near Bailey Island ](https://www.expedia.com/Car-Rentals-In-Bailey-Island.d6046825.Car-Rental-Guide)
- [Enterprise Rental Cars in Bailey Island ](https://www.expedia.com/Enterprise-Car-Rentals-In-Bailey-Island.d6046825-c15.Car-Rental-Guide-Suppliers)
- [Car rentals near Sebasco ](https://www.expedia.com/Car-Rentals-In-Sebasco.d553248635975749228.Car-Rental-Guide)
- [Car rentals near Sebascodegan Island ](https://www.expedia.com/Car-Rentals-In-Sebascodegan-Island.d553248635975859087.Car-Rental-Guide)
- [Car rentals near Sebasco Estates ](https://www.expedia.com/Car-Rentals-In-Sebasco-Estates.d180774.Car-Rental-Guide)

- [Orrs Island Vacation Rentals ](https://www.expedia.com/Orrs-Island-Vacation-Rentals.d3000440072.Travel-Guide-VacationRentals)
- [Bailey Island Vacation Rentals ](https://www.expedia.com/Bailey-Island-Vacation-Rentals.d6046825.Travel-Guide-VacationRentals)
- [Hermit Island Vacation Rentals ](https://www.expedia.com/Hermit-Island-Vacation-Rentals.d6341836.Travel-Guide-VacationRentals)

- [Things to do in Harpswell ](https://www.expedia.com/Things-To-Do-In-Harpswell.d553248635077688915.Travel-Guide-Activities)

\* 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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