Great Diamond Island Romantic Vacations

Book a Romantic Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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 Romantic vacation packages in Great Diamond Island

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

Portland Harbor Hotel

Downtown Portland
$590
per person
Dec 10 - Dec 13
found 12 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.2/10 Wonderful! (1,864 reviews)
Inn By The Sea

Inn By The Sea

$931
per person
Dec 10 - Dec 13
found 12 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (333 reviews)
The Weldon Hotel

The Weldon Hotel

Downtown Portland
$823
per person
Dec 10 - Dec 13
found 12 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.8/10 Exceptional! (122 reviews)
This was the best accommodation in Portland that we have stayed at—by a wide margin. The building and unit itself are a dream. Spacious, quiet, elevated, fresh, clean, thoughtful touches, quality finishes and materials, comfortable, inviting, secure…I have nothing but praise for this property. My spouse and I waxed lyrical about it for the entire stay, “Oh my goodness, I wish we lived here.”, and “we’re home!”. Of course we were happy to get back to our real home back in Boston after our time at the Weldon came to a close, but it was sincerely a “home away from home” experience top to bottom. Book this place—you’ve found the one.

Reviewed on Oct 9, 2026

Kennebunkport Captains Collection

Kennebunkport Captains Collection

$1,051
per person
Dec 10 - Dec 13
found 2 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (751 reviews)
Old world charm, took you right back to the days of old and had you wondering what life was like back then. Appreciated the bikes to ride, rooms were excellent with the slight gribe that a little more light in the room would have been nice. Breakfasts were top notch.

Reviewed on Oct 7, 2026

Longfellow Hotel

Longfellow Hotel

Parkside
$785
per person
Dec 10 - Dec 13
found 2 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (192 reviews)
This hotel is amazing. Friendly staff- really good food and the spa was great.

Reviewed on Sep 21, 2026

Don't see what you're looking for?
See all available trips from Columbus to Great Diamond Island
View all trips

5* Romantic vacations in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.
White Barn Inn & Spa, Auberge Collection

White Barn Inn & Spa, Auberge Collection

$1,090
per person
Dec 18 - Dec 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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 Romantic vacations in Great Diamond Island

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

Portland Harbor Hotel

Downtown Portland
$590
per person
Dec 10 - Dec 13
found 12 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.2/10 Wonderful! (1,864 reviews)
Inn By The Sea

Inn By The Sea

$931
per person
Dec 10 - Dec 13
found 12 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (333 reviews)
The Weldon Hotel

The Weldon Hotel

Downtown Portland
$823
per person
Dec 10 - Dec 13
found 12 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.8/10 Exceptional! (122 reviews)
This was the best accommodation in Portland that we have stayed at—by a wide margin. The building and unit itself are a dream. Spacious, quiet, elevated, fresh, clean, thoughtful touches, quality finishes and materials, comfortable, inviting, secure…I have nothing but praise for this property. My spouse and I waxed lyrical about it for the entire stay, “Oh my goodness, I wish we lived here.”, and “we’re home!”. Of course we were happy to get back to our real home back in Boston after our time at the Weldon came to a close, but it was sincerely a “home away from home” experience top to bottom. Book this place—you’ve found the one.

Reviewed on Oct 9, 2026

Don't see what you're looking for?
See all available trips from Columbus to Great Diamond Island
View all trips

4 Night Romantic vacations in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

Downtown Portland
$1,068
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.6/10 Exceptional! (400 reviews)
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

Downtown Portland
$1,122
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.6/10 Exceptional! (70 reviews)
This place was wonderful! The staff was incredibly helpful and it was a time location for things to do and places to eat, all within walking distance. Would definitely recommend and stay again

Reviewed on Oct 7, 2026

Evalina Hotel

Evalina Hotel

Downtown Portland
$1,403
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
10/10 Exceptional! (13 reviews)
Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation system?) from a nearby establishment audible during business hours. Well, if you pick a hotel in the middle of things, you get the noise and bustle that comes from being in the middle of things. That said, we’d come again, but shoot for a penthouse/upper floor unit farther from the street-level mania.

Reviewed on Oct 5, 2026

Don't see what you're looking for?
See all available trips from Columbus to Great Diamond Island
View all trips

How to find a romantic Great Diamond Island vacation

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 $590. 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?

Things to do

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

$77
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

$59
per adult
80% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
Sunset Lighthouse Cruise Along Casco Bay

Sunset Lighthouse Cruise Along Casco Bay

$69
per adult
Sunset Lighthouse Cruise Along Casco Bay
See all activities in Great Diamond Island

More vacations you might like

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