Deals on vacations and trips to Great Diamond Island

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Great Diamond Island flight + hotel vacation packages

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Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $674, price is now $527 per person
$527
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Portland (PWM)
Free WiFi in public areas, a terrace, and a garden are available at this bed & breakfast. Enjoy the free on-the-go breakfast each morning. Concierge services are provided for your convenience.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,467, price is now $1,152 per person
$1,152
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
This bed & breakfast features free WiFi in public areas, concierge services, and self parking. Enjoy the free self-serve breakfast each morning. Luggage storage is also provided.
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was $815, price is now $654 per person
$654
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Portland (PWM)
This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out is also provided.
84 Main

84 Main

4 out of 5
Price was $1,304, price is now $1,053 per person
$1,053
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. Luggage storage and laundry facilities are also provided.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,341, price is now $1,119 per person
$1,119
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. Luggage storage and concierge services are also provided.

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
$91 nightly
The price is $101 total per night
$101 total
Dec 6 - Dec 7
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
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free Cancellation
$76 nightly
The price is $84 total per night
$84 total
Nov 18 - Nov 19
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
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Free Cancellation
Reserve now, pay when you stay
$77 nightly
The price is $86 total per night
$86 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
Hot Tub
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $187 total per night
$187 total
Nov 22 - Nov 23
Total with taxes and fees
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
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Free Cancellation
$61 nightly
The price is $66 total per night
$66 total
Nov 18 - Nov 19
Total with taxes and fees
This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.
Breakfast included
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
Free Cancellation
Reserve now, pay when you stay
$83 nightly
The price is $90 total per night
$90 total
Nov 22 - Nov 23
Total with taxes and fees
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
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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.

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 $527. 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

A calm sea with a sailboat and rocky coastline.
A large house with a red roof and a wooden dock extending into a body of water.
A house with a red roof on stilts over water, surrounded by trees and a grassy hill.
A dock with a small building, people, and colorful items.

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