Great Diamond Island Vacation Packages 2025 from $452

Great Diamond Island flight + hotel vacation packages

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

Nautical Mile by Capital Vacations

per person

Apr 9 - Apr 13

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

A seasonal outdoor pool is featured at this aparthotel, along with free self parking. A picnic area and a computer station are also provided.

Cliff House Maine

Save 100% on your flight

per person

Mar 20 - Mar 24

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

84 Main

per person

Mar 6 - Mar 10

found 7 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) 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.

The Harraseeket Inn & Event House

per person

Feb 17 - Feb 24

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Portland (PWM)

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking.

Hilton Garden Inn Freeport Downtown

per person

Feb 17 - Feb 24

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Portland (PWM)

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

Top Great Diamond Island hotels deals

Portland Harbor Hotel

468 Fore Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$177

includes taxes & fees

$160 per night

Jan 21 - Jan 22

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.

Pet friendly

Free WiFi

Canopy by Hilton Portland Waterfront

9 Center Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$150

includes taxes & fees

$135 per night

Jan 27 - Jan 28

This hotel features 2 restaurants and a 24-hour gym. WiFi in public areas is free. Valet parking, a lobby fireplace, and a communal living room are also offered.

Pet friendly

Free WiFi

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$134

includes taxes & fees

$122 per night

Jan 26 - Jan 27

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

Holiday Inn Portland-By the Bay, an IHG Hotel

88 Spring St, Portland, ME

Free Cancellation

$108

includes taxes & fees

$98 per night

Jan 20 - Jan 21

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.

Tru by Hilton Portland Airport Area

369 Maine Mall Road, South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$88

includes taxes & fees

$81 per night

Feb 2 - Feb 3

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 Regency Hotel & Spa

20 Milk Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$165

includes taxes & fees

$149 per night

Jan 22 - Jan 23

A full-service spa, a spa 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.

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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

4.5/5(88 reviews)

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

Portland Museum of Art

4.5/5(255 reviews)

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

Victoria Mansion

4.5/5(121 reviews)

You can find out about the history of Portland with a trip to Victoria Mansion. Experience the area's acclaimed theater scene and entertainment choices.

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 $452. 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.