Great Diamond Island Romantic Vacations 2026

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Top Romantic vacation packages in Great Diamond Island

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

Portland Harbor Hotel

Downtown Portland

$594

per person

Nov 8 - Nov 11

found 23 hours ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.2/10 Wonderful! (1,791 reviews)

The Weldon Hotel

Downtown Portland

$644

per person

Nov 8 - Nov 11

found 23 hours ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.8/10 Exceptional! (107 reviews)

The unit was great. The kitchen and it's utensils are excellent. The turntable record player gives a classic wonderful back in time. We would suggest more soaking towels under the sink. And keep the corner of the rug not in the living room not slippery. Other than that it was a wonderfully clean and high end place to stay close to the Old Port.

Reviewed on Aug 24, 2026

White Barn Inn & Spa, Auberge Collection

Save 100% on your flight

$5,386

per person

Oct 7 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

9.4/10 Exceptional! (123 reviews)

An amazing experience. Wonderful place, wonderful accommodation (we had the loft suite). Staff was great and smiling.

Reviewed on Aug 10, 2026

Inn By The Sea

$813

per person

Nov 8 - Nov 11

found 23 hours ago

Roundtrip flight included

Chicago (CHI) 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

$1,460

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Portland (PWM)

9.4/10 Exceptional! (733 reviews)

Such a great location and very nice house. I would recommend to anyone traveling, we lived it. Only thing to think about is the beds a a tad small. Other than that, it’s great.

Reviewed on Aug 24, 2026

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5* Romantic 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

$5,386

per person

Oct 7 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

9.4/10 Exceptional! (123 reviews)

An amazing experience. Wonderful place, wonderful accommodation (we had the loft suite). Staff was great and smiling.

Reviewed on Aug 10, 2026

Don't see what you're looking for?

See all available trips from Columbus to Great Diamond Island

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3 Night Romantic vacations in Great Diamond Island

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

The Weldon Hotel

Downtown Portland

$644

per person

Nov 8 - Nov 11

found 23 hours ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.8/10 Exceptional! (107 reviews)

Reviewed on Aug 24, 2026

Inn By The Sea

$813

per person

Nov 8 - Nov 11

found 23 hours ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.6/10 Exceptional! (328 reviews)

Reviewed on Aug 13, 2026

Kennebunkport Captains Collection

$1,460

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Portland (PWM)

9.4/10 Exceptional! (733 reviews)

Such a great location and very nice house. I would recommend to anyone traveling, we lived it. Only thing to think about is the beds a a tad small. Other than that, it’s great.

Reviewed on Aug 24, 2026

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See all available trips from Columbus to Great Diamond Island

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4 Night Romantic vacations in Great Diamond Island

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

Ogunquit River Inn & Suites

Moody

Save 100% on your flight

$621

per person

Sep 25 - Sep 29

found 14 hours ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9/10 Wonderful! (1,011 reviews)

The environment, especially the sound from the river.

Reviewed on Aug 25, 2026

Blind Tiger Portland - Danforth Street.

West End

Save 100% on your flight

$1,680

per person

Oct 21 - Oct 25

found 7 hours ago

Roundtrip flight included

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

9.6/10 Exceptional! (189 reviews)

Perfect location & beautiful stay! Very unique property. Great recommendations & lovely hospitality. We will definitely come back the next time we’re in Portland! :)

Reviewed on Aug 23, 2026

Portland Harbor Hotel

Downtown Portland

Save 100% on your flight

$1,411

per person

Sep 28 - Oct 2

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Portland (PWM)

9.2/10 Wonderful! (1,791 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Great Diamond Island

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How can I find the best Great Diamond Island vacation packages for couples?

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Great Diamond Island romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering and visiting outside busy months of .

How can I plan a great romantic trip to Great Diamond Island?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Great Diamond Island?

Put a price on love with stunning deals for duos starting at just $594. Stay during the quiet season, in , for breaks to make your bank balance smile. Prices and availability are subject to change. Additional terms may apply.

Can I book Great Diamond Island spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

What’s the best time of year for a romantic vacation in Great Diamond Island?

Book your romantic getaway during the quieter months of when you can have the place to yourself, pretty much. To show your partner off to the world, provide a more abundant audience.

How can I book romantic weekend getaway packages in Great Diamond Island?

To book a loved-up break in Great Diamond Island, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

Can I book a romantic trip to Great Diamond Island with free cancellation and/or flexible dates?

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Great Diamond Island romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?