
Great Diamond Island Vacations from $304
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The Latest Great Diamond Island vacation packages
Price found within the past 48 hours. Click for updated prices.

Kennebunkport Captains Collection
Price was $381, price is now $304 per person
$304
per person
Jan 30 - Feb 1
found 7 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
18.8/10 Exceptional! (649 reviews)
Room was so comfortable and clean. Fireplace was a nice amenity. Great shower. Staff was so friendly and kind. Delicious breakfast. Wonderful location, fantastic stay.
Reviewed on Nov 19, 2025

Blind Tiger Portland - Danforth Street.
West End
Price was $452, price is now $340 per person
$340
per person
Jan 23 - Jan 25
found 20 hours ago
Roundtrip non-stop flight included
New York (LGA) to Portland (PWM)
19.2/10 Exceptional! (161 reviews)
Wish they had a liquor license and could do a cocktail hour in addition to a breakfast service. Wish they had just a tad more breakfast options. Really wish they had a key pad and front door access! LOVED the fire places in every room. Property manager was lovely and friendly. Loved the snacks available and variety.
Reviewed on Oct 27, 2025

Cliff House Maine
Save 100% on your flight
Price was $764, price is now $590 per person
$590
per person
Jan 30 - Feb 1
found 7 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
18.8/10 Exceptional! (1,001 reviews)
What an amazing experience! Definitely heading back there
Reviewed on Nov 18, 2025

Blind Tiger Portland – Carleton Street
West End
Price was $584, price is now $456 per person
$456
per person
Jan 23 - Jan 25
found 20 hours ago
Roundtrip non-stop flight included
New York (LGA) to Portland (PWM)
19.2/10 Exceptional! (119 reviews)
Adorable spot in Portland, great location, really cool concept. Felt like an upgraded vacation rental. You don’t have the whole place to yourself but it basically feels like it. Check in and everything was seamless. The local recommendations, games, and snacks were a nice touch. We loved plays scrabble and drinking wine in the parlor. We do wish some items were a bit nicer given the cost. The bathroom could've had nicer facilities (cheap toilet seat, low water pressure) our bed was a rickety. The breakfast delivered was a nice touch but the contents itself kinda fell flat, not as curated as the website made it seem. Overall we still enjoyed our stay and the concept, but the website may have upsold it a bit.
Reviewed on Nov 11, 2025

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See all available trips from Columbus to Great Diamond Island
View all tripsDiscover the most popular places to visit in Great Diamond Island

State Theatre
4.5/5(88 reviews)
The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.

Portland Museum of Art
4.5/5(255 reviews)
Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

East End Beach
Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.
What to do in Great Diamond Island

Portland Smartphone Audio Tour: Self-Guided Drive
$17
per traveler

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
$10
per traveler
Great Diamond Island Hotel Deals

Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is $92 total per night from Nov 30 to Dec 1
$92 total
per night
Nov 30 - Dec 1
7.8/10 Good! (1,231 reviews)
Room was clean.everything worked . Staff was helpful and friendly.
Reviewed on Nov 11, 2025

The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is $98 total per night from Dec 7 to Dec 8
$98 total
per night
Dec 7 - Dec 8
8.8/10 Excellent! (1,000 reviews)
Clean room. Staff corrected a booking issue promptly.
Reviewed on Nov 9, 2025

Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is $157 total per night from Nov 23 to Nov 24
$157 total
per night
Nov 23 - Nov 24
9.2/10 Wonderful! (1,676 reviews)
Excellent location, helpful front desk, quiet, clean, well-appointed room.
Reviewed on Nov 18, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Great Diamond Island Vacation Packages
Great Diamond Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




















