Great Diamond Island Vacation Packages 2025 from $651

Great Diamond Island flight + hotel vacation packages

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

Best Western Freeport Inn

per person

Aug 1 - Aug 6

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Portland (PWM)

This hotel doesn't skimp on freebies - guests receive 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 an off-leash area. There's a seasonal outdoor pool on site, and a 24-hour front desk and express check-out are also provided.

Portland Harbor Hotel

Downtown Portland

Save 100% on your flight

per person

Aug 29 - Sep 2

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) 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.

Blind Tiger Portland – Carleton Street

West End

Save 100% on your flight

per person

Aug 29 - Sep 2

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Portland (PWM)

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free local cuisine breakfast each morning. A terrace and a garden are also provided.

The Docent's Collection

Downtown Portland

Save 100% on your flight

per person

Aug 29 - Sep 2

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) 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.

Ogunquit River Inn & Suites

per person

Aug 15 - Aug 18

found 1 hour ago

Roundtrip flight included

Cleveland (CLE) to Portland (PWM)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a seasonal outdoor pool on site, and a terrace and a garden are also provided.

Top Great Diamond Island hotels deals

Inn at Diamond Cove

22 Mckinley Court, Great Diamond Island, Portland, ME

Free Cancellation

Reserve now, pay when you stay

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A marina, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Make the most of the gym and outdoor tennis court, and relax with drinks at one of the 3 bars/lounges.

Pool

Free WiFi

La Quinta Inn & Suites by Wyndham Portland

340 Park Ave, Portland, ME

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This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and a free airport shuttle. Business travelers can take advantage of the business center. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

The Westin Portland Harborview

157 High St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

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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

Inn at St John Portland In-Town

939 Congress St, Portland, ME

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This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A lobby fireplace, a computer station, and luggage storage are also on offer.

Breakfast included

Pet friendly

Canopy by Hilton Portland Waterfront

9 Center Street, Portland, ME

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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 Harbor Hotel

468 Fore Street, Portland, ME

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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

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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 great live music.

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 $651. 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.