Kid friendly Vacations in Great Diamond Island 2026

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Flight and Kid friendly hotel deals in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.

Canopy by Hilton Portland Waterfront

Downtown Portland

CA $830

per person

Dec 4 - Dec 6

found 1 hour ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

9.4/10 Exceptional! (1,006 reviews)

Cliff House Maine

Bald Head

CA $3,718

per person

Oct 8 - Oct 12

found 6 hours ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

9.4/10 Exceptional! (1,001 reviews)

The Westin Portland Harborview

Downtown Portland

CA $1,823

per person

Oct 11 - Oct 16

found 17 hours ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

9/10 Wonderful! (1,005 reviews)

Great lication, clean, nice hotel.

Reviewed on Sep 8, 2026

Holiday Inn Portland-By the Bay by IHG

Downtown Portland

CA $1,585

per person

Oct 11 - Oct 16

found 17 hours ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

9/10 Wonderful! (1,633 reviews)

Staff was very friendly and helpful. The room was spacious and comfortable. The location is very good. It's not right in the heart of the tourist district, but very close by. Portland is a walking city anyway. Word to the wise: we had a spectacular view of the ocean. Pay the extra few dollars to get this view - it is worth it.

Reviewed on Sep 7, 2026

Inn By The Sea

CA $1,579

per person

Nov 4 - Nov 7

found 23 hours ago

Roundtrip non-stop flight included

Edmonton (YEA) to Portland (PWM)

9.6/10 Exceptional! (328 reviews)

Lovely property. Very well maintained and taken care of. The option of pool or beach is a plus. Although we didn’t utilize the activities available each day.. it seemed very family friendly. Definitely will be back but hopefully reserve a bigger room or suite. Charming outdoor seating on the huge lawn but mostly in the sun. An indoor lobby with some comfy seating would be great.

Reviewed on Aug 13, 2026

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3 Night Kid friendly holidays in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.

Portland Harbor Hotel

Downtown Portland

CA $1,272

per person

Nov 4 - Nov 7

found 23 hours ago

Roundtrip non-stop flight included

Edmonton (YEA) to Portland (PWM)

9.2/10 Wonderful! (1,828 reviews)

Staff was great, but rooms and amenities were incredibly dated. The bathroom had no ventilation, a very old shower, and mediocre product options. The rooms were very bare bones and not warm or inviting. There was nothing all that special about this property and certainty not worth the nightly rate.

Reviewed on Sep 6, 2026

Inn By The Sea

CA $1,579

per person

Nov 4 - Nov 7

found 23 hours ago

Roundtrip non-stop flight included

Edmonton (YEA) to Portland (PWM)

9.6/10 Exceptional! (328 reviews)

Reviewed on Aug 13, 2026

The Weldon Hotel

Downtown Portland

CA $1,663

per person

Nov 4 - Nov 7

found 23 hours ago

Roundtrip non-stop flight included

Edmonton (YEA) to Portland (PWM)

9.8/10 Exceptional! (115 reviews)

My Husband and I are road tripping to PEI and stopped in Portland to do sightseeing and rest up. The king guest suite was awesome to say the least. Check in was better than standard big hotel. Free parking just steps away, great walkable location to shops and waterfront. As a construction professional, the place was done with care and detail and loaded with smart amenities. I could easily live here. New bedding and comfortable. Amanda gave great local tourist information. Ate at Dry Dock and had the best Fish and Chips and fish tacos. Don’t pass this unique stay up!!!!

Reviewed on Sep 5, 2026

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4 Night Kid friendly holidays in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.

Ogunquit River Inn & Suites

Moody

CA $1,246

per person

Oct 8 - Oct 12

found 6 hours ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

9/10 Wonderful! (1,016 reviews)

Everything was great

Reviewed on Sep 7, 2026

The Docent's Collection at 121 Middle Street

Downtown Portland

CA $3,153

per person

Oct 8 - Oct 12

found 6 hours ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

9.6/10 Exceptional! (377 reviews)

The Docent's Collection at 178 Middle Street

Downtown Portland

CA $2,885

per person

Oct 8 - Oct 12

found 6 hours ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

9.6/10 Exceptional! (58 reviews)

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What are some benefits of booking a family-friendly vacation?

Whether it's luxurious or cheap, family vacations in Great Diamond Island are among the most memorable experiences you'll ever have with your family. It can be a great way to bond and explore new destinations with the people you love most. Plus, it's easy to keep an eye on your little ones without having to worry about how they are with a sitter back home. You may even meet some other families and establish long-lasting friendships.

How can I find the best family-friendly vacations?

Using search filters makes finding the perfect family-friendly vacation easy. You can implement the search filter for family-friendly accommodations specifically, but that's just the beginning. You'll also find search filters for price range along with the desired number of bedrooms, so you can ensure you have enough space for everyone you want to bring to Great Diamond Island.

Are there cheap family vacations to Great Diamond Island?

Price varies quite a bit, ranging from to . The price you'll be paying depends on a variety of factors, and you can filter for them all. You can implement a filter for your budget limitations and also remove any 4- and 5-star stays from your search. You can even filter by accommodation type, which can present you with cheap alternatives to what is typically considered standard.

When should I book family-friendly vacation packages?

The right time to book family-friendly vacation packages in Great Diamond Island depends on what you're looking for. If you're looking to save, booking during least popular month tends to be cheaper compared to the rest of the year, though that's not always a guarantee. Keep in mind that the off-season and the busy season differ from place to place, with family-friendly vacations in Canada being very different compared to options in France and Spain, for example.

Can I book an all-inclusive family vacation in Great Diamond Island?

Yes, you'll find plenty of all-inclusive family vacation packages for Great Diamond Island. To see what's available, just select the all-inclusive filter on your search.

How can I book the best family activity vacation?

If you're looking to make the most out of the available activities in Great Diamond Island, you'll need to consider what your family likes to do. Cater your itinerary to your family's interests, and you'll create memories that you and your kids will hold on to for the rest of your lives whether it's family ski vacations in Great Diamond Island or something a bit more relaxed.

Can I find luxury family vacations in Great Diamond Island?

If you're looking for a luxury family vacation to Great Diamond Island, you can use search filters to find the best options available. Activate the filter for 5-star packages to only see the best of the best. Plus, you'll find a range of first-class flights available to make even the journey there top-of-the-line.

How can I search for family vacation deals?

Finding deals is easy when you take advantage of the array of available search filters. You can set budget limitations and remove 4- and 5-star options from your search. If you don't want to miss out on your favourite amenities, however, you can consider travelling during , which often have lower prices because of the off-season in Great Diamond Island.

Can I book a family vacation package that is fully refundable?

If you're looking for a fully refundable reservation, you won't have to look far on Expedia. Quite a few properties in Great Diamond Island are fully refundable. You can search for this feature, but always make sure to check the specific property's policies and requirements before booking.

Why should I book my family trip with Expedia?

When you book with Expedia, you can book your accommodation and your flight together, with some discounts available for doing both at once. Additionally, you may be able to enjoy special discounts with Expedia Rewards that will earn you points you can then put toward discounts for subsequent bookings.