Great Diamond Island Vacation Packages 2026 from $502

Great Diamond Island flight + hotel vacation packages

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

Portland Harbor Hotel

Downtown Portland

$502

per person

Apr 21 - Apr 25

found 1 day 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 Docent’s Collection – Thompson Block

Downtown Portland

$535

per person

Apr 21 - Apr 25

found 1 day 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.

The Weldon Hotel

Downtown Portland

$538

per person

Apr 21 - Apr 25

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Portland (PWM)

A 24-hour gym, self parking, and a virtual front desk are featured at this aparthotel. 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. Free WiFi in public areas is also provided.

84 Main

$764

per person

Mar 28 - Apr 3

found 7 hours ago

Roundtrip non-stop flight included

Raleigh (RDU) to Portland (PWM)

This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. Luggage storage and laundry facilities are also provided.

Blind Tiger Portland - Danforth Street.

West End

$667

per person

Apr 21 - Apr 25

found 1 day 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 Diamond Island hotels deals

The Westin Portland Harborview

157 High St Portland ME

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$108 total

Mar 2 - Mar 3

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

$77 nightly

$85 total

Feb 19 - Feb 20

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

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$163 total

Feb 16 - Feb 17

Total with taxes and fees

Pet friendly

Free WiFi

Old Orchard Beach Inn

6 Portland Ave Old Orchard Beach ME

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$95 total

Feb 15 - Feb 16

Total with taxes and fees

A seasonal outdoor pool, free self parking, and wedding services are featured at this bed & breakfast. WiFi in public areas is free. A garden, a library, and a picnic area are also on offer.

Pool

Parking included

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$141 total

Mar 1 - Mar 2

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

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$128 total

Feb 26 - Feb 27

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

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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

State Theatre

You can make plans for a show at State Theatre during your trip to Portland. Experience the area's acclaimed theater scene and great live music.

Portland Museum of Art

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

East End Beach

If a restful vacation is part of your travel plans, East End Beach might be the perfect place to seek out during your trip to Portland.

Frequently asked questions

How much are vacation packages to Great Diamond Island?

Exciting adventures await you in Great Diamond Island, with Travelocity vacation packages starting from just $502. Including hotels and flights, these amazing deals make it easy to experience more of our wonderful planet.

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

With at least 400 partner airlines and 1,000,000 properties all over the world, you can't go wrong with Travelocity. Scroll through our comprehensive range and score an incredible Great Diamond Island package deal. Isn't it amazing when vacation planning is that easy?

Why should I purchase my Great Diamond Island vacation package with Travelocity?

Whether you're planning a month-long vacation or a last-minute trip, we have plenty of amazing destinations to choose from at a good price. In addition, we provide round-the-clock support, top-notch service and a Price Match Guarantee. Save yourself the effort and time and lock in your dream vacation today.

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

You certainly can with our Great Diamond Island vacation packages. With one of these, there are loads of ways to make your travel budget go further. Bundle any two or more car, flight, hotel and tour bookings and see the savings grow. With a rental car, all the landmarks in and around Great Diamond Island are an unforgettable road trip away.