Great Diamond Island Vacation Packages 2024/2025 from $738

Great Diamond Island flight + hotel vacation packages

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

Portland Harbor Hotel

Downtown Portland

per person

Feb 4 - Feb 11

found 13 hours ago

Roundtrip flight included

Detroit (DTW) 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

Downtown Portland

Save 100% on your flight

per person

Feb 4 - Feb 11

found 13 hours ago

Roundtrip flight included

Detroit (DTW) to Portland (PWM)

This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out and dry cleaning are also provided.

The Weldon Hotel

Downtown Portland

per person

Feb 4 - Feb 11

found 13 hours ago

Roundtrip flight included

Detroit (DTW) 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 McKernan Inn

per person

Feb 4 - Feb 11

found 13 hours ago

Roundtrip flight included

Detroit (DTW) to Portland (PWM)

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

Waldo Emerson Inn

per person

Feb 4 - Feb 11

found 13 hours ago

Roundtrip flight included

Detroit (DTW) to Portland (PWM)

This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free 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 and an off-leash area. A business center, a terrace, and a garden are also on offer.

Top Great Diamond Island hotels deals

La Quinta Inn & Suites by Wyndham Portland

340 Park Ave, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$91

includes taxes & fees

$83 per night

Nov 27 - Nov 28

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

Casco Bay Hotel, Ascend Hotel Collection

80 John Roberts Rd., South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$78

includes taxes & fees

$71 per night

Dec 8 - Dec 9

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Business travelers can take advantage of the free WiFi in public areas. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.

Breakfast included

Free airport shuttle

Portland Harbor Hotel

468 Fore Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$193

includes taxes & fees

$175 per night

Dec 10 - Dec 11

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

$136

includes taxes & fees

$123 per night

Dec 8 - Dec 9

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

Portland Regency Hotel & Spa

20 Milk Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$187

includes taxes & fees

$169 per night

Nov 26 - Nov 27

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.

Hot Tub

Spa

Hyatt Place Portland-Old Port

433 Fore St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

$143

includes taxes & fees

$129 per night

Dec 16 - Dec 17

The hotel's indoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. A restaurant, a 24-hour front desk, and a coffee shop are also provided.

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 acclaimed theater scene 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.

Eastern Promenade

5/5(1 review)

Explore the great outdoors at Eastern Promenade, a lovely green space in Portland. Stroll along the waterfront or attend a sporting event in the area.

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 $738. 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.