Great Island Vacation Packages 2026 from $373

Great Island flight + hotel vacation packages

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

Portland Harbor Hotel

Downtown Portland

$373

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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.

Inn By The Sea

$1,142

per person

Apr 9 - Apr 16

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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.

The McKernan Inn

$451

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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.

Blind Tiger Portland - Danforth Street.

West End

$1,068

per person

Apr 9 - Apr 16

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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.

The Docent’s Collection – Thompson Block

Downtown Portland

$433

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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.

Top Great Island hotels deals

The Westin Portland Harborview

157 High St Portland ME

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$108 total

Feb 8 - Feb 9

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

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

Reserve now, pay when you stay

$78 nightly

$87 total

Jan 22 - Jan 23

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

Long Creek Hotel by IHG

171 Philbrook Ave South Portland ME

Free Cancellation

$78 nightly

$85 total

Jan 22 - Jan 23

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like on-the-go breakfast and free self parking.

Pool

Hot Tub

Holiday Inn Portland-By the Bay by IHG

88 Spring St Portland ME

Free Cancellation

$78 nightly

$86 total

Jan 29 - Jan 30

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

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$143 total

Jan 22 - Jan 23

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

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$136 total

Jan 27 - Jan 28

Total with taxes and fees

Pet friendly

Free WiFi

Don't see what you're looking for?

See all available properties in Great Island

View all properties

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

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.

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.

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 $373. 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.