Great Island Vacation Packages 2026 from $415

Great Island flight + hotel vacation packages

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

Portland Harbor Hotel

Downtown Portland

$415

per person

Mar 16 - Mar 19

found 19 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.

The McKernan Inn

$507

per person

Mar 16 - Mar 19

found 19 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

This inn features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a picnic area, and luggage storage are also on offer.

The Docent’s Collection – Thompson Block

Downtown Portland

$479

per person

Mar 16 - Mar 19

found 19 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out is provided and the front desk is staffed around-the-clock.

Inn By The Sea

$584

per person

Mar 16 - Mar 19

found 19 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the playground, onsite laundry facilities, and free supervised childcare. Enjoy the outdoor pool and perks like free valet parking.

Blind Tiger Portland - Danforth Street.

West End

$562

per person

Mar 16 - Mar 19

found 19 hours ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

This bed & breakfast doesn't skimp on freebies - guests receive free breakfast and free WiFi. Luggage storage and concierge services are also provided.

Top Great Island hotels deals

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

Reserve now, pay when you stay

$78 nightly

$87 total

Jan 15 - Jan 16

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and perks like free self parking and a free cruise terminal shuttle.

Pool

Hot Tub

The Westin Portland Harborview

157 High St Portland ME

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$117 total

Feb 4 - Feb 5

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Spa

Pet friendly

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$132 nightly

$147 total

Feb 3 - Feb 4

Total with taxes and fees

A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a roundtrip airport shuttle. There's a gym on site, and laundry facilities and concierge services are also offered.

Hot Tub

Spa

Tru by Hilton Portland Airport Area

369 Maine Mall Road South Portland ME

Free Cancellation

Reserve now, pay when you stay

$67 nightly

$73 total

Feb 8 - Feb 9

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Free airport shuttle

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$136 nightly

$150 total

Jan 25 - Jan 26

Total with taxes and fees

Pet friendly

Free WiFi

Holiday Inn Portland-By the Bay by IHG

88 Spring St Portland ME

Free Cancellation

$78 nightly

$86 total

Jan 19 - Jan 20

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free area shuttle.

Pool

Free airport shuttle

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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.

Popular places to visit

Bailey Island Bridge

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.

Paddleworks

Enjoy an outing to Paddleworks during your stay in Orrs Island. Wander the seaside and beaches in the area.

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.

Frequently asked questions

How much are vacation packages to Great Island?

With a Travelocity vacation package, you could be living it up in Great Island for a mere $415. Flights, tours and hotels — we have it all. You'll make great savings just for bundling together your bookings. And with all of that taken care of before you even go, you won't have a care in the world.

Where can I get the best vacation package deals for Great Island?

There are fantastic Great Island package deals to be gained with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties across the globe? Keep that in mind the next time you're ready to check another place off the old bucket list.

Why should I book my Great Island vacation package with Travelocity?

Because life is an amazing journey, and we have everything you could hope for to help you along the way. With our top-quality service and Price Match Guarantee, you can book your trip with confidence. Plus, you can sleep easy while you're on the road knowing we're here for you with our 24/7 support.

Can I save on my Great Island car rental if I combine it with my hotel or flight?

You certainly can with our Great Island vacation packages. With one of these, there are lots of ways to stretch your vacation budget further. Combine any two or more car, flight, hotel and tour bookings and watch your savings pile up. With a rental car, all the main sights around Great Island are a memorable road trip away.

Which airport is best for Great Island?

For passengers visiting Great Island, the most used airports are Portland Intl. Jetport Airport (PWM), Knox County Regional Airport (RKD) and Augusta State Airport (AUG).

What is there to do in Great Island?

Great Island is full to the brim with amazing things to see and do, however Paddleworks and Land's End Gift Shop are among the best of them.