Great Diamond Island Vacations from $683

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The Latest Great Diamond Island vacation packages

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

The Meadowmere Resort

$683
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
8.6/10 Excellent! (1,009 reviews)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

West End
Save 100% on your flight
$2,237
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (189 reviews)
This hotel is amazing. The rooms, beds, and all the details are so incredible. I wish I could have stayed longer. Check in was a breeze as well. You can tell they take a lot of care and thought into the property. I will definitely be back

Reviewed on Jul 25, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

Moody
$939
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
The hotel staff were pleasant, helpful, and welcoming. The lobby is well maintained. The room we stayed in was spacious, clean and had more toiletries than I expected. It is about 2-miles from the main intersection that has shops, restaurants and the beach, but the Ogunquit Trolley stops right in front of the hotel. The trolley runs from 9AM-9PM from 7/1 - 10/15 (cash only). For anyone considering this hotel, I would strongly recommend it.

Reviewed on Aug 10, 2026

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

West End
Save 100% on your flight
$1,960
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (128 reviews)
Evalina Hotel

Evalina Hotel

Downtown Portland
Save 100% on your flight
$1,326
per person
Oct 22 - Oct 25
found 2 days ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
10/10 Exceptional! (7 reviews)
It was our first time visiting Portland, and the Evalina exceeded our expectations. The location is perfect, right on Commercial Street, with plenty of restaurants and shops nearby. The ferry and cruise ports are also just a 5–10 minute walk away, making it easy to visit the different islands. The suite was comfortable and thoughtfully equipped with everything we could need, including an umbrella for rainy days, coffee and a French press, tea, a washer and dryer, and so much more. Communication was excellent throughout our stay as well. We truly enjoyed our visit, and the next time we’re in Portland, the Evalina will be our first choice!

Reviewed on Aug 8, 2026

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What to do in Great Diamond Island

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 Lighthouse Boat Cruise with Oysters & Prosecco

Portland Explorer: Boat Cruise with Oysters & Prosecco

$137
per adult
Portland Explorer: Boat Cruise with Oysters & Prosecco
Portland, Maine: Tour in Vintage Fire Engine

Portland, Maine: Tour in Vintage Fire Engine

$45
per adult
90% of travellers recommend
Portland, Maine: Tour in Vintage Fire Engine
See all activities in Great Diamond Island

Great Diamond Island Hotel Deals

Clarion Pointe South Portland

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME
Fully refundable
$93 nightly
$101 total
Sep 9 - Sep 10
Total with taxes and fees
Clarion Pointe South Portland
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME
Fully refundable
$131 nightly
$145 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (1,624 reviews)
"It did the job for 3 nights. A little out dated, the mattress felt like a old school spring bed. Bathroom small and could have been updated. Positive: pricing, close to Thompson Point, and cheap Uber to downtown Portland"

Reviewed on Aug 10, 2026

Clarion Hotel Portland Airport ME
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

738 Main Street South Portland ME
Fully refundable
$96 nightly
$105 total
Aug 17 - Aug 18
Total with taxes and fees
6.4/10 (1,043 reviews)
"Dejeuner était bon et pour le prix payer c'était très bien."

Reviewed on Aug 11, 2026

Quality Inn & Suites South Portland
See all 2,451 properties in Great Diamond Island
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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