Great Island Vacation Packages 2026 from $587

Great Island flight + hotel vacation packages

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

Grasshopper Inn

Save 100% on your flight

$587

per person

May 29 - May 31

found 1 day ago

Roundtrip flight included

New York (NYC) to Portland (PWM)

This inn features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free cooked-to-order breakfast each morning. A communal living room, a picnic area, and express check-in are also on offer.

Cliff House Maine

Bald Head

Save 100% on your flight

$1,090

per person

May 23 - May 26

found 1 day ago

Roundtrip flight included

New York (NYC) to Portland (PWM)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, laundry service, and valet parking. Relax with a drink at one of the 2 poolside bars and enjoy perks like free self parking.

Blind Tiger Portland - Danforth Street.

West End

Save 100% on your flight

$841

per person

May 15 - May 18

found 13 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

Ogunquit River Inn & Suites

$684

per person

May 22 - May 25

found 13 hours ago

Roundtrip flight included

New York (JFK) to Portland (PWM)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a seasonal outdoor pool on site, and a terrace and a garden are also provided.

Portland Harbor Hotel

Downtown Portland

$707

per person

May 20 - May 23

found 22 hours ago

Roundtrip flight included

Baltimore (BWI) 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.

Top Great Island hotels deals

The Westin Portland Harborview

157 High St Portland ME

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$126 total

Apr 26 - Apr 27

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

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Free Cancellation

$134 nightly

$149 total

Apr 20 - Apr 21

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking and a safe deposit box are also offered on site.

Pet friendly

Free WiFi

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$170 nightly

$188 total

Apr 26 - Apr 27

Total with taxes and fees

Pet friendly

Free WiFi

Holiday Inn Portland-By the Bay by IHG

88 Spring St Portland ME

Free Cancellation

$93 nightly

$103 total

Apr 14 - Apr 15

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

$122 nightly

$135 total

Apr 20 - Apr 21

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

Hyatt Place Portland Downtown - Old Port Square

433 Fore St Portland ME

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$119 total

Apr 13 - Apr 14

Total with taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Valet parking, a coffee shop, and a snack bar/deli are also offered.

Free airport shuttle

Pet friendly

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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.

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 $587. 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.