Great Diamond Island Vacation Packages 2025/2026 from $620

Great Diamond Island flight + hotel vacation packages

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

Hilton Garden Inn Portland Airport

$620

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Portland (PWM)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. There's a gym on site, and a 24-hour front desk and a terrace are also provided.

Portland Harbor Hotel

Downtown Portland

$642

per person

Dec 23 - Dec 27

found 1 day 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.

Inn By The Sea

$863

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip flight included

Baltimore (BWI) 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 Docent's Collection - New Opening

Downtown Portland

$822

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Portland (PWM)

This hotel features free WiFi in public areas, concierge services, and self parking. 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. Luggage storage is also provided.

Hilton Garden Inn Portland Downtown Waterfront

Downtown Portland

$665

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Portland (PWM)

This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and laundry facilities.

Top Great Diamond Island hotels deals

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Free Cancellation

Reserve now, pay when you stay

$83 nightly

$92 total

Nov 20 - Nov 21

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

The Westin Portland Harborview

157 High St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$98 total

Dec 1 - Dec 2

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.

Portland Harbor Hotel

468 Fore Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$165 nightly

$183 total

Nov 23 - Nov 24

Total with taxes and fees

Pet friendly

Free WiFi

DoubleTree by Hilton Hotel Portland

363 Maine Mall Rd South Portland ME

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$88 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free self parking and a free airport shuttle. A business center, a coffee shop, and free WiFi in public areas are also on offer.

Fireside Inn & Suites Portland

81 Riverside St Portland ME

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$105 total

Nov 21 - Nov 22

Total with taxes and fees

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

Pool

Pet friendly

Holiday Inn Portland-By the Bay by IHG

88 Spring St Portland ME

Free Cancellation

$78 nightly

$86 total

Nov 30 - Dec 1

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

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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 great live music and entertainment choices.

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 $620. 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.