Great Diamond Island Kid friendly Vacations 2026

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Top Kid friendly vacation packages in Great Diamond Island

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

Portland Harbor Hotel

Downtown Portland

$864

per person

Nov 15 - Nov 20

found 18 hours ago

Roundtrip flight included

Dallas (DAL) 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

$1,430

per person

Nov 15 - Nov 20

found 17 hours ago

Roundtrip flight included

Dallas (DAL) 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

Kennebunkport Captains Collection

$2,022

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Portland (PWM)

9.4/10 Exceptional! (736 reviews)

It was a charming and authentic historic stay in a great location close to everything. The staff were super friendly and helpful. And the bed was divinely comfortable!

Reviewed on Sep 6, 2026

Longfellow Hotel

Parkside

$904

per person

Nov 15 - Nov 20

found 17 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

9.6/10 Exceptional! (186 reviews)

Oceanfront Home - Beach Access - Deck + Ping Pong

Save 100% on your flight

$5,044

per person

Nov 20 - Nov 27

found 7 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

No reviews

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3 Night Kid friendly vacations in Great Diamond Island

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

Canopy by Hilton Portland Waterfront

Downtown Portland

$710

per person

Nov 14 - Nov 17

found 17 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

9.4/10 Exceptional! (1,006 reviews)

Room design very simple and elegant

Reviewed on Sep 4, 2026

Inn By The Sea

$791

per person

Nov 14 - Nov 17

found 20 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

9.6/10 Exceptional! (328 reviews)

Reviewed on Aug 13, 2026

Portland Harbor Hotel

Downtown Portland

$1,105

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

9.2/10 Wonderful! (1,828 reviews)

Reviewed on Sep 6, 2026

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4 Night Kid friendly vacations in Great Diamond Island

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

Blind Tiger Portland – Carleton Street

West End

$796

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip flight included

New York (NYC) to Portland (PWM)

9.6/10 Exceptional! (129 reviews)

Evalina Hotel

Downtown Portland

Save 100% on your flight

$1,086

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip flight included

New York (NYC) to Portland (PWM)

10/10 Exceptional! (11 reviews)

The Docent's Collection at 178 Middle Street

Downtown Portland

$1,087

per person

Oct 24 - Oct 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

9.6/10 Exceptional! (58 reviews)

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How can I find the best family vacation packages in Great Diamond Island?

For fam-tastic vacation packages in Great Diamond Island, check the family-friendly filter and add child-charming amenities, like water parks and pools. Read reviews written by other broods to be sure your chosen stay packs plenty of rest and play.

How can I book family-friendly vacations in Great Diamond Island on a budget?

For family- and wallet-friendly trips, filter your search results by budget. You can also sort by price. When bringing the whole brigade on a budget, consider staying in low season or outside the city or. To save more coin, accommodation with a kitchen can be your friend—a bowl of pasta at home is always cheaper than feeding the team at a restaurant.

What does a family trip to Great Diamond Island cost?

You could book your amazing family trip to Great Diamond Island just $710. But with so many brilliant breaks on offer, there’s something for every wallet. Prices and availability are subject to change. Additional terms may apply.

When is the best time of year for family vacations to Great Diamond Island?

If you’re crowd-cautious, the quieter months of are positively perfect in Great Diamond Island. But it’s if you’d rather mingle with the masses. Match your wardrobe to the weather and it’s always a wonderful time to visit Great Diamond Island.

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

Check the all-inclusive filter for an all-you-could-ever-wish-for family vacay. Click more of your favorite filters for even more extravagance. Perhaps an ocean view, spa, or hot tub. Maybe a water park, epic kids club, or activities galore.

How can I plan a fun family vacation in Great Diamond Island?

Search for stays with kid-satisfying extras, like water parks, and teenage-friendly free Wi-Fi, so they can post about all their vacation adventures for all their buddies back home. Book up local attractions, excursions, and experiences—and they might even put their phone down for a few minutes.

How can I find Great Diamond Island family vacation deals?

Delightful deals often dwell outside high season, so move your travel dates around for top deals. You can also book up a little away from the major Great Diamond Island landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains.

Can I book a Great Diamond Island family vacation package with free cancellation and/or flexible dates?

Free cancellation makes for a hassle-free family vacation. Filter by payment option to find fully flexible trips, including buy now, pay later options.

Why should I book my Great Diamond Island family trip with Expedia?

You can easily find fun for all the family with the super-handy filters. It’s easy to build your dream kid-friendly vacation in just a few clicks. And you can bundle your accommodation, airfare, and car rental in just a few more.