Great Diamond Island Vacation Packages

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Top Great Diamond Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Casco Bay Hotel, Ascend Hotel Collection

Casco Bay Hotel, Ascend Hotel Collection

3.5 out of 5
per person
Oct. 29 - Nov. 4
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
8.6/10 Excellent! (2,038 reviews)
Close to airport and had a shuttle

Reviewed on Sep. 21, 2024

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Oct. 29 - Nov. 4
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (948 reviews)
There were dirty underwear and socks in a drawer. I expected them to move us out of the room but the manager just apologized. Not a big deal for me but the proper thing to do would have been to get customers out of the room. Instead we waited 1/2 hour for staff to come and remove and clean- I was disappointed. This was an anniversary get away We made reservations at their restaurant and I had requested champagne at the table because I was surprising my wife with a ring. They forgot the champagne. Apologized at the end. Picked up dessert. I expected much better at the cost of this property. Lovely property all in all

Reviewed on Sep. 23, 2024

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
per person
Oct. 29 - Nov. 4
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (172 reviews)
Great spot for downtown Portland

Reviewed on Sep. 11, 2024

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Oct. 29 - Nov. 4
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,319 reviews)
Beautiful hotel, spacious rooms, within walking distance to shops and restaurants. Friendly and helpful staff

Reviewed on Sep. 22, 2024

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Oct. 29 - Nov. 4
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (762 reviews)
Nice, clean hotel. Friendly staff

Reviewed on Sep. 17, 2024

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Great Diamond Island Hotel Deals

Casco Bay Hotel, Ascend Hotel Collection
Casco Bay Hotel, Ascend Hotel Collection
3.5 out of 5
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $107 per night from Oct. 20 to Oct. 21
CA $107
CA $117 total
includes taxes & fees
Oct 20 - Oct 21
8.4/10 Very Good! (2,112 reviews)
"Close to airport and had a shuttle"

Reviewed on Sep. 21, 2024

Casco Bay Hotel, Ascend Hotel Collection
Ramada Plaza by Wyndham Portland
Ramada Plaza by Wyndham Portland
3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Oct. 21 to Oct. 22
CA $142
CA $157 total
includes taxes & fees
Oct 21 - Oct 22
7.6/10 Good! (1,028 reviews)
"The staff was very friendly and courtesy"

Reviewed on Sep. 21, 2024

Ramada Plaza by Wyndham Portland
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $446 per night from Sep. 29 to Sep. 30
CA $446
CA $545 total
includes taxes & fees
Sep 29 - Sep 30
9/10 Wonderful! (1,345 reviews)
"For time spent walking around the harbor area of Portland-this hotel is perfect. Note: valet parking is $45 but you do receive a notice in advance and compared to options close by and peace of mind that your car is secure is worth it. Also-a $35 resort fee but if you eat/drink on the property they ..."

Reviewed on Sep. 22, 2024

Portland Harbor Hotel
See all 2,188 properties in Great Diamond Island
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Great Diamond Island vacation package cost?
Less than you might think — from just CA $724, as a matter of fact! By combining hotels, flights and car rentals into your own custom-built travel package, your getaway to Great Diamond Island is just clicks away.
How do I get a cheap travel package to Great Diamond Island?
Bundle your hotel and flight bookings, throw in extras such as activities or a rental car, and save with a Great Diamond Island vacation package. You won’t just walk away with awesome discounts on your adventure — you’ll have loads of choice at your fingertips too. When you book with Expedia, you’ll have your pick of over 550 partner airlines and 1,000,000 hotels worldwide. Your dream vacation starts right here, right now!
How far in advance should I book my Great Diamond Island vacation?
Smart travelers often book as early as possible. You can usually look up international airfares on Expedia up to 12 months before your flight. If you’ve left booking to the last minute, don’t despair. Bargain prices sometimes appear just weeks prior to departure.
What does an Expedia Great Diamond Island travel package include?
Hotels, flights and rental cars, or any combination of them — it’s totally up to you. Whether you’re venturing to Great Diamond Island with the kids or adventuring solo, there’s a package to suit your budget and style. Once you’ve made your booking, why not add on some tours or activities?
What should I know before booking a Great Diamond Island travel package?
When you book your hotels, flights and car rentals together, you’ll score awesome discounts. Whether you’re organizing a rural escape in a cottage or would rather stay in a fancy hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Great Diamond Island Expedia vacation package?
You sure can. We have more than 550 partner airlines around the world, so opt for the carrier that fits your needs.
If I'm not able to travel, can I cancel my Great Diamond Island vacation package?
It’s impossible to predict what the future holds, so it’s comforting to know that you can cancel or change your Great Diamond Island vacation package. If your booking was made in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Discover the most popular places to visit in Great Diamond Island

Image for State Theatre

State Theatre

4.5/5(5 reviews)

The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.

State Theatre
Image for Portland Museum of Art

Portland Museum of Art

5/5(5 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
Image for Victoria Mansion

Victoria Mansion

4/5(9 reviews)

Visit the remarkably preserved 19th-century manor house, located in downtown Portland. Get an authentic impression of life during that era.

Victoria Mansion

What to do in Great Diamond Island

Image for Lighthouse Lovers Cruise in Portland

Lighthouse Lovers Cruise in Portland

CA $53
Per adult
100% of travellers recommend
Lighthouse Lovers Cruise in Portland
Image for Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

CA $13
Per adult
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Image for Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

CA $84
Per adult
Afternoon Windjammer Cruise Along the Coast of Portland Maine
See all activities in Great Diamond Island

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.