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

$390

per person

Jan 11 - Jan 14

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Portland (PWM)

9.2/10 Wonderful! (1,851 reviews)

84 Main

$599

per person

Dec 17 - Dec 20

found 4 hours ago

Roundtrip non-stop flight included

Houston (HOU) to Portland (PWM)

9.8/10 Exceptional! (58 reviews)

The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.

Reviewed on Jul 17, 2026

Inn By The Sea

$571

per person

Jan 11 - Jan 14

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Portland (PWM)

9.6/10 Exceptional! (333 reviews)

Great pet friendly resort that allowed the dog to remain in the room while dining in the restaurant. Pet was allowed in the lounge area where they offered the same dining room menu, if you wanted to bring you pet along . Pet treats and food and water dishes already in place in the room.

Reviewed on Oct 22, 2026

White Barn Inn & Spa, Auberge Collection

Save 100% on your flight

$1,827

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

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

9.6/10 Exceptional! (124 reviews)

Cliff House Maine

Bald Head

$936

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

9.4/10 Exceptional! (1,002 reviews)

Clean room, beautiful views, great that you can get coffee or tea at stations. Menu was expensive for what you get and not enough choices

Reviewed on Oct 22, 2026

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5* Kid friendly vacations in Great Diamond Island

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

White Barn Inn & Spa, Auberge Collection

Save 100% on your flight

$1,827

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

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

9.6/10 Exceptional! (124 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Great Diamond Island

View all trips

3 Night Kid friendly vacations in Great Diamond Island

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

Portland Harbor Hotel

Downtown Portland

$390

per person

Jan 11 - Jan 14

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Portland (PWM)

9.2/10 Wonderful! (1,851 reviews)

84 Main

$599

per person

Dec 17 - Dec 20

found 4 hours ago

Roundtrip non-stop flight included

Houston (HOU) to Portland (PWM)

9.8/10 Exceptional! (58 reviews)

The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.

Reviewed on Jul 17, 2026

Inn By The Sea

$571

per person

Jan 11 - Jan 14

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Portland (PWM)

9.6/10 Exceptional! (333 reviews)

Reviewed on Oct 22, 2026

Don't see what you're looking for?

See all available trips from Columbus to Great Diamond Island

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4 Night Kid friendly vacations in Great Diamond Island

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

Portland Harbor Hotel

Downtown Portland

$595

per person

Jan 13 - Jan 17

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

9.2/10 Wonderful! (1,851 reviews)

Inn By The Sea

$784

per person

Jan 6 - Jan 10

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

9.6/10 Exceptional! (333 reviews)

Reviewed on Oct 22, 2026

Canopy by Hilton Portland Waterfront

Downtown Portland

$1,063

per person

Dec 30 - Jan 3

found 1 day ago

Roundtrip flight included

Washington (DCA) to Portland (PWM)

9.4/10 Exceptional! (1,007 reviews)

Great stay & great location!

Reviewed on Oct 20, 2026

Don't see what you're looking for?

See all available trips from Columbus to Great Diamond Island

View all trips

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 $390. 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.

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.