Great Diamond Island Vacation Packages
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Top Great Diamond Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $1,512, price is now CA $1,293 per person
CA $1,293
per person
Dec 10 - Dec 13
found 17 hours ago
Roundtrip flight included
Toronto (YTZ) to Portland (PWM)
9.6/10 Exceptional! (419 reviews)
We loved everything. The only thing is the mattress is a little soft and you easily roll to the middle!
Reviewed on Oct 27, 2026
Great Diamond Island Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Nov 19 to Nov 20
CA $151
CA $167 total
Nov 19 - Nov 20
includes taxes & fees
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
The price is CA $113 per night from Nov 11 to Nov 12
CA $113
CA $126 total
Nov 11 - Nov 12
includes taxes & fees
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
The price is CA $101 per night from Nov 19 to Nov 20
CA $101
CA $110 total
Nov 19 - Nov 20
includes taxes & fees
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.
What to do in Great Diamond Island
Harbor Lights and Sights Cruise
CA $86
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $109
per adult
92% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
CA $83
per adult
80% of travellers recommend
Frequently asked questions
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- Beach Hotel Hotels in Portland
- Cheap Hotels in Portland
- Holiday Inn Express Hotel & Suites South Portland by IHG
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- Hotels with Free Parking in Portland
- Munjoy Hill Hotels
- Home2 Suites by Hilton Portland Airport
- Tru by Hilton Portland Airport Area
- South Portland Hotels
- Downtown Portland Hotels
- Family Hotels in Portland
- Boutique Hotels in Portland
- Hotels near Cross Insurance Arena
- Best Western Merry Manor Inn
- Hotels near Portland Intl. Jetport
- Hotels near Maine Mall
- Hotels with Kitchenettes in Portland
- Hotels near Thompson's Point
- Blind Tiger Portland
- B&B in Portland
- Quality Inn & Suites South Portland
- Cottages in Portland
- Oceanfront Hotels in Portland
- Courtyard by Marriott Portland Airport
- Old Orchard Beach Hotels
- Portland Hotels
- Clarion Pointe South Portland
- Cheap Hotels in South Portland
- Inn On Peaks Island
- Doubletree by Hilton Hotel Portland
- Pet-Friendly Hotels in Portland
- Hotels with Free Breakfast in Portland
- Old Port Hotels
- Pet-Friendly Hotels in Great Diamond Island
- Long Creek Hotel by IHG
- Cabin Rentals in Portland
- Portland Sheraton at Sable Oaks
- Ogunquit Hotels
- Comfort Inn South Portland Airport
- Waterpark Hotels in Portland
- Freeport Hotels
- Beach Hotel Hotels in Old Orchard Beach
- Motels in Portland
- Hotels with Free Airport Shuttle in Portland
- Flights from Moncton (YQM) to Portland (PWM)
- Flights from Halifax (YHZ) to Portland (PWM)
- Flights from Vancouver (YVR) to Portland (PWM)
- Flights to Great Diamond Island
- Flights from Ottawa (YOW) to Portland (PWM)
- Flights from Portland Intl. Jetport
- Flights from Edmonton (YEG) to Portland (PWM)
- Flights from Calgary (YYC) to Portland (PWM)
- Flights from Fredericton (YFC) to Portland (PWM)
- Flights from Detroit (DTW) to Portland (PWM)
- Flights to Portland
- Flights from Toronto (YYZ) to Portland (PWM)
- Flights from Montreal (YUL) to Portland (PWM)
- Flights from Buffalo (BUF) to Portland (PWM)
- Flights from Boston (BOS) to Portland (PWM)
- Portland Museum of Art
- Gooch's Beach
- Popham Beach State Park
- Westbrook Vacations
- Casco Vacations
- Camp Ellis Beach
- Higgins Beach
- Ll Bean Flagship Store
- Old Orchard Beach Pier
- East End Beach
- Freeport Vacations
- Portland Vacations
- Portland Head Light
- Visit Ferry Village
- Maine Mall
- South Portland Vacations
- Ogunquit Beach
- Desert of Maine
- Seashore Trolley Museum
- Windham Vacations
- Marden's Surplus and Salvage
- Palace Playland
- Visit Portland
- Bailey Island Vacations
- Kennebunkport Vacations
- Scarborough Vacations
- Scarborough Beach State Park
- Durham Vacations
- Aquaboggan Water Park
- Visit Old Orchard Beach
- Old Orchard Beach Vacations
- Visit Old Port
- Ocean Park Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
