Deals on vacations and trips to Great Diamond Island

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Great Diamond Island flight + hotel vacation packages

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

River View Resort

2.5 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
This motel features an indoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. Enjoy the sauna and conveniences like a terrace and barbecue grills.
Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
This bed & breakfast 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. A coffee shop, a garden, and a snack bar/deli are also on offer.
The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 31 - Sep 7
found 20 hours ago
Roundtrip non-stop flight included
Columbus (CMH) 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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 31 - Sep 7
found 20 hours ago
Roundtrip non-stop flight included
Columbus (CMH) 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 McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.

Top Great Diamond Island hotels deals

Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
22 Mckinley Court, Great Diamond Island, Portland, ME
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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

La Quinta Inn & Suites by Wyndham Portland

3 out of 5
340 Park Ave, Portland, ME
Free Cancellation
Reserve now, pay when you stay
Get rates
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

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Free Cancellation
Reserve now, pay when you stay
Get rates
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

Inn at St John Portland In-Town

2.5 out of 5
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

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
Get rates
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

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
Get rates
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 showing street scenes as well as an individual femail

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.

State Theatre
Portland Museum of Art showing art and interior views as well as a small group of people

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.

Portland Museum of Art
East End Beach which includes general coastal views and a beach as well as a small group of people

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.

East End Beach

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 $722. 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.

Photos of local treasures

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Photo by Robbie Martin
Photo by Robbie Martin