Great Diamond Island Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Great Diamond Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Inn at St John Portland In-Town
Valley Street
$1,268
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and Cross Insurance Arena are located nearby.
Small breakfast area. Clerk not at all friendly. Bad neighborhood lots of homeless.
Reviewed on Sep 17, 2026
The Westin Portland Harborview
Downtown Portland
$1,662
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Portland Head Light are located nearby.
We enjoyed our stay, clean and comfortable rooms and a nice roof top bar. Close to shops and restaurants about a 20 minute walk to the waterfront.
Reviewed on Sep 17, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
$2,733
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Thompson's Point and Portland Head Light are located nearby.
Immaculate furnishings, hardware, linens, etc. More a rental apt or upscale AirBNB than an inn. Fine if that is what you were expecting. I was expecting more atmosphere (sterile) and service (minimal}.
Indifferent rating for service reflects a combination of staff belaboring obvious points on check in while being unresponsive on follow-up. Example: wanted to leave my bag there after an early checkout so I could spend a few hours around town prior to moving on. That proved too difficult…might as well have been dealing with robots.
Reviewed on Sep 16, 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
$2,481
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
Beautiful room and location. Didn't really use the amenities
Reviewed on Sep 14, 2026
Portland Regency Hotel & Spa
Downtown Portland
$1,980
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
Excellent location, great front of house staff. Historical building. Well designed rooms. Shuttle from airport.
Reviewed on Sep 15, 2026
Portland Harbor Hotel
Downtown Portland
$2,559
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
Lovely building, great responsive staff. The bistro terrace is fantastic, as well as the fire pit. We’ll likely stay here again if we come back to the area.
Reviewed on Sep 17, 2026
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See all available trips from Columbus to Great Diamond Island
View all tripsGreat Diamond Island Vacation Packages
Trying to save both time and money on your upcoming vacation to Great Diamond Island? The AARP Travel Center Powered by Expedia® can help you do both. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Great Diamond Island perfect. Our Travel Center is a one-stop shop where you can put together the best vacation package for you and your family. We have an amazing choice of accommodations and flight, as well as Great Diamond Island activities to pick from.
Great Diamond Island Hotels
You can choose from around 2406 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Great Diamond Island hot spots, we have plenty of options available.
From Great Diamond Island hotels with multiple pools and on-site restaurants, to boutique accommodations that add all the extra touches, you'll find a hotel here that will make your trip one to remember. With AARP Travel Center's Great Diamond Island hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Great Diamond Island
The fact that you are traveling to Great Diamond Island means your trip is already off to a terrific start. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
If you are looking for more, then head over to our "Things to Do" page for more inspiration or to book an activity in Great Diamond Island.
Book Together and Save
As an AARP Member, you get to take advantage of all the great savings. You can save on select hotels worldwide, flights, and even car rentals. No matter what Great Diamond Island vacation bundle you pick, your membership savings helps you get a great deal. So what are you waiting for? Bundle today and get ready for your Great Diamond Island vacation.
Top Hotel Deals
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's ...
Comfort Inn South Portland Airport
90 Maine Mall Rd South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
Portland Harbor Hotel
468 Fore Street Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff ...
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
The Westin Portland Harborview
157 High St Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Inn at St John Portland In-Town
939 Congress St Portland ME
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Oceanfront Studio w/ Private Dock in Harpswell!
Harpswell ME
Stay at this apartment in Harpswell. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Mitchell Field and Bailey Island Bridge ...
Spark by Hilton Portland Airport Maine Mall
461 Maine Mall Rd South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Embassy Suites by Hilton Portland Maine
1050 Westbrook Street Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
Don't see what you're looking for?
See all available properties in Great Diamond Island
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Jan 9 - Wed, Jan 20
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$179
Roundtrip
found 3 days ago
Tue, Nov 10 - Tue, Nov 17
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$219
Roundtrip
found 2 days ago
Tue, Nov 10 - Tue, Nov 17
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$227
Roundtrip
found 2 days ago
Tue, Nov 10 - Tue, Nov 17
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$227
Roundtrip
found 2 days ago
Tue, Nov 10 - Tue, Nov 17
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$277
Roundtrip
found 2 days ago
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All accommodation types in Great Diamond Island
More Types of Hotels
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