Great Diamond Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Great Diamond Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Inn at St John Portland In-Town

Inn at St John Portland In-Town

Valley Street
CA $738
per person
Oct 19 - Oct 23
found 21 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
8.6/10 Excellent! (1,118 reviews)
The Inn was a charming place to stay with it's quirky room layouts and charming lobby. The staff was exceedingly helpful. It IS a hundred year old Inn so you need to expect the "charm" over modern upgrades. We found the breakfast to be convenient with a substantial selection. It was a little further from the Port area - just a warning if you plan on walking "into town" Lovely place and we thoroughly enjoyed our stay!!

Reviewed on Sep 17, 2026

Portland Harbor Hotel

Portland Harbor Hotel

Downtown Portland
CA $1,574
per person
Oct 19 - Oct 23
found 21 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
9.2/10 Wonderful! (1,823 reviews)
I was disappointed. Overall, the hotel was nice, but I didn't like my room. It was on a busy street corner on the second floor, so very loud street noises, compounded by the construction outside. They were full, so couldn't move us. The room was also a handicap accessible room, so very barren looking. No light switch in the bathroom either and very dim lighting in the bathroom. Was not happy, particularly for the price.

Reviewed on Sep 17, 2026

The Meadowmere Resort

The Meadowmere Resort

CA $1,008
per person
Oct 19 - Oct 23
found 21 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
8.6/10 Excellent! (1,005 reviews)
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

Moody
CA $884
per person
Oct 19 - Oct 23
found 21 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
9/10 Wonderful! (1,016 reviews)
Unique hotel experience, great free breakfast

Reviewed on Sep 17, 2026

Kennebunkport Captains Collection

Kennebunkport Captains Collection

CA $1,481
per person
Oct 19 - Oct 23
found 21 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
9.4/10 Exceptional! (736 reviews)
We had a wonderful stay at the Nathaniel Lord Mansion. It was the right blend of having super helpful staff around but at the same time feeling like you were on your own in your own home. I loved that they thought of all of the little things you would care about like water for your room, sweet treats (the cookies were great) and how to get around. We also liked that we could easily walk to everything but we also used the bikes for exploring a bit further away. It was a delightful stay all around.

Reviewed on Sep 16, 2026

Ready to book your vacation to Great Diamond Island?

Choose your dates

Great Diamond Island Hotel Deals

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

80 John Roberts Rd. South Portland ME
Fully refundable
CA $153
per night
Oct 18 - Oct 19
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

738 Main Street South Portland ME
Fully refundable
CA $123
per night
Oct 18 - Oct 19
6.4/10 (1,132 reviews)
"Older facility without an elevator, which is challenging for older guests with heavy luggage who are staying on the 2nd floor. Staff were courteous and helpful."

Reviewed on Sep 17, 2026

Quality Inn & Suites South Portland
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
CA $151
per night
Oct 18 - Oct 19
Clarion Hotel Portland Airport ME
See all 2,397 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.

What to do in Great Diamond Island

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

CA $107
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland: Casco Bay Morning Lighthouse Cruise

Portland: Casco Bay Morning Lighthouse Cruise

CA $82
per adult
Portland: Casco Bay Morning Lighthouse Cruise
See all activities in Great Diamond Island

Frequently asked questions

How much does a Great Diamond Island vacation package cost?
Less than you might think — from just CA $738, 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.

Explore a world of travel with Expedia

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