Great Diamond Island Vacation Packages 2026 from $638

Great Diamond Island flight + hotel vacation packages

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

Portland Regency Hotel & Spa

Downtown Portland

$638

per person

May 6 - May 10

found 6 hours ago

Roundtrip flight included

Minneapolis (MSP) to Portland (PWM)

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.

The Weldon Hotel

Downtown Portland

Save 100% on your flight

$834

per person

May 6 - May 10

found 6 hours ago

Roundtrip flight included

Minneapolis (MSP) 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.

The Docent’s Collection – Thompson Block

Downtown Portland

Save 100% on your flight

$890

per person

May 6 - May 10

found 6 hours ago

Roundtrip flight included

Minneapolis (MSP) 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.

Blind Tiger Portland - Danforth Street.

West End

Save 100% on your flight

$1,040

per person

May 6 - May 10

found 6 hours ago

Roundtrip flight included

Minneapolis (MSP) 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.

Portland Harbor Hotel

Downtown Portland

$712

per person

May 6 - May 10

found 6 hours ago

Roundtrip flight included

Minneapolis (MSP) 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 Diamond Island hotels deals

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.

Portland Harbor Hotel

468 Fore Street Portland ME

Free Cancellation

Reserve now, pay when you stay

$148 nightly

$164 total

Feb 18 - Feb 19

Total with taxes and fees

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

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.

Tru by Hilton Portland Airport Area

369 Maine Mall Road South Portland ME

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$81 total

Feb 23 - Feb 24

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.

Hampton Inn Portland Downtown - Waterfront

209 Fore St Portland ME

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$99 total

Feb 22 - Feb 23

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the free buffet breakfast each morning.

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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 $638. 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.