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.
The Kennebunk Inn

The Kennebunk Inn

2.5 out of 5
per person
May 31 - Jun 5
found 1 hour ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a grocery/convenience store, and a library are also on offer.
Nautical Mile

Nautical Mile

2.5 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 16
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
A seasonal outdoor pool is featured at this aparthotel, along with free self parking. A picnic area and a computer station are also provided.
Waldo Emerson Inn

Waldo Emerson Inn

3 out of 5
per person
May 31 - Jun 5
found 1 hour ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A business center, a terrace, and a garden are also on offer.
The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 25
found 9 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 16
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.

Top Great Diamond Island hotels deals

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
The price is $143 per night
$143
includes taxes & fees
$129 per night
May 11 - May 12
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

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $225 per night
$225
includes taxes & fees
$204 per night
Apr 28 - Apr 29
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
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $181 per night
$181
includes taxes & fees
$164 per night
Apr 27 - Apr 28
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking and a safe deposit box are also offered on site.
Pet friendly
Free WiFi
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $93 per night
$93
includes taxes & fees
$84 per night
Apr 30 - May 1
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
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
939 Congress St, Portland, ME
The price is $97 per night
$97
includes taxes & fees
$89 per night
Apr 27 - Apr 28
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
La Quinta Inn & Suites by Wyndham Portland

La Quinta Inn & Suites by Wyndham Portland

2.5 out of 5
340 Park Ave, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $99 per night
$99
includes taxes & fees
$89 per night
Apr 30 - May 1
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
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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 great live music and entertainment choices.

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 $941. 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

Browse Great Diamond Island vacation photos for more inspiration

Photo by Robbie Martin
Photo by Robbie Martin