Great Diamond Island Vacation Packages 2025/2026 from $304

Great Diamond Island flight + hotel vacation packages

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

Hampton Inn Portland Downtown - Waterfront

Downtown Portland

$304

per person

Feb 6 - Feb 9

found 13 hours ago

Roundtrip flight included

Dallas (DAL) to Portland (PWM)

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.

Portland Harbor Hotel

Downtown Portland

Save 100% on your flight

$317

per person

Feb 6 - Feb 9

found 13 hours ago

Roundtrip flight included

Dallas (DAL) 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.

Cliff House Maine

Save 100% on your flight

$928

per person

Feb 6 - Feb 9

found 13 hours ago

Roundtrip non-stop flight included

Dallas (DAL) 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.

Portland Regency Hotel & Spa

Downtown Portland

$357

per person

Feb 6 - Feb 9

found 13 hours ago

Roundtrip flight included

Dallas (DAL) 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.

Kennebunkport Captains Collection

$707

per person

Feb 6 - Feb 9

found 13 hours ago

Roundtrip non-stop flight included

Dallas (DAL) to Portland (PWM)

This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A garden, luggage storage, and concierge services are also on offer.

Top Great Diamond Island hotels deals

Clarion Hotel Portland

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

Nov 30 - Dec 1

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

Portland Harbor Hotel

468 Fore Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$165 nightly

$183 total

Nov 16 - Nov 17

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.

Pool

Free airport shuttle

Fireside Inn & Suites Portland

81 Riverside St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$110 total

Nov 15 - Nov 16

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

4.5/5(88 reviews)

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

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.

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 $304. 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.