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.
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
per person
Aug. 22 - Aug. 29
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
7.8/10 Good! (1,008 reviews)
Ok but nothing special

Reviewed on Jun. 16, 2024

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Jul. 22 - Jul. 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (902 reviews)
Outstanding views and customer service!

Reviewed on Jun. 17, 2024

Waldo Emerson Inn

Waldo Emerson Inn

3 out of 5
Save 100% on your flight
per person
Jul. 22 - Jul. 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8.6/10 Excellent! (313 reviews)
Great place to relax and wind down. The innkeepers where excellent.

Reviewed on Oct. 28, 2023

White Barn Inn & Spa, Auberge Resorts Collection

White Barn Inn & Spa, Auberge Resorts Collection

5 out of 5
Save 100% on your flight
per person
Jul. 22 - Jul. 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (75 reviews)
Very attentive. Valet even plugged in my plug-in hybrid Toyota

Reviewed on Jun. 12, 2024

Hidden Pond

Hidden Pond

4 out of 5
Save 100% on your flight
per person
Jul. 22 - Jul. 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8/10 Very Good! (6 reviews)
The service was not top notch for the price. Family pool was too small. Spa lacked a sauna and steam and had a small waiting area. We liked the overall ambiance, charming main lobby and outdoor shower in the room. The room overall was good. But other than the person at checkout who was great, we did not feel the other service people were excited to have us there.

Reviewed on Jun. 17, 2024

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 $177 per night from Jun. 18 to Jun. 19
CA $177
CA $193 total
includes taxes & fees
Jun 18 - Jun 19
8.4/10 Very Good! (1,607 reviews)
"Good solid stay close to hospital for 2 night layover. Clean, pleasant, friendly."

Reviewed on Jun. 15, 2024

Casco Bay Hotel, Ascend Hotel Collection
The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $372 per night from Jul. 1 to Jul. 2
CA $372
CA $423 total
includes taxes & fees
Jul 1 - Jul 2
8.4/10 Very Good! (1,049 reviews)
"All staff we encountered were incredibly kind and helpful. Beautiful, clean and well-located hotel."

Reviewed on Jun. 14, 2024

The Westin Portland Harborview
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 $399 per night from Jul. 1 to Jul. 2
CA $399
CA $494 total
includes taxes & fees
Jul 1 - Jul 2
9/10 Wonderful! (1,208 reviews)
"Good location and walkable."

Reviewed on Jun. 17, 2024

Portland Harbor Hotel
See all 2,140 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 $1,006, 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 LL Bean Flagship Store

LL Bean Flagship Store

4.5/5(50 reviews)

During your trip to Freeport, you can enjoy retail therapy at LL Bean Flagship Store. Stroll along the area's waterfront or simply enjoy its seafood restaurants.

LL Bean Flagship Store
Image for Higgins Beach

Higgins Beach

4.5/5(8 reviews)

At the mouth of the Spurwink River in Scarborough, take a stroll on the white sand or paddle a kayak over gentle waves.

Higgins Beach
Image for Portland Head Light

Portland Head Light

4.5/5(27 reviews)

Look out across the Atlantic Ocean from Portland’s iconic white lighthouse, which has presided over the southern Maine coastline since the 18th century.

Portland Head Light

What to do in Great Diamond Island

Image for Portland: Old Port Seafood Lovers Tour

Portland: Old Port Seafood Lovers Tour

CA $198
Per adult
Portland: Old Port Seafood Lovers Tour
Image for Sunset Lighthouse Harbor Cruise from Portland's Old Port

Sunset Lighthouse Harbor Cruise from Portland's Old Port

CA $122
Per adult
Sunset Lighthouse Harbor Cruise from Portland's Old Port
Image for Portland, Maine: Old Port Brewery & Pub Walking Tour

Portland, Maine: Old Port Brewery & Pub Walking Tour

CA $121
Per adult
Portland, Maine: Old Port Brewery & Pub Walking Tour
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.