Great Diamond Island Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Great Diamond Island vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Portland Harbor Hotel
Downtown Portland
9.2/10 Wonderful! (1,823 reviews)
Oct 25 - Oct 29
4 night stay
Cincinnati (CVG) to Portland (PWM)
Southwest Airlines • Non-stop roundtrip • Coach
Price was $973, price is now $751 per person
$751
per person
found 1 day ago
The front desk ladies were the best!
Reviewed on Sep 21, 2026
3.5-star property
The Docent's Collection at 121 Middle Street
Downtown Portland
9.6/10 Exceptional! (382 reviews)
Oct 25 - Oct 29
4 night stay
Cincinnati (CVG) to Portland (PWM)
Southwest Airlines • Non-stop roundtrip • Coach
Price was $1,057, price is now $852 per person
$852
per person
found 1 day ago
Other than being a little hard to find, this spot was wonderful and so much nicer than a hotel room! Great location.
Reviewed on Sep 18, 2026
3.5-star property
The Docent's Collection at 178 Middle Street
Downtown Portland
9.6/10 Exceptional! (61 reviews)
Oct 25 - Oct 29
4 night stay
Cincinnati (CVG) to Portland (PWM)
Southwest Airlines • Non-stop roundtrip • Coach
Price was $1,054, price is now $850 per person
$850
per person
found 1 day ago
Staff was very very good and super quick to respond.. I really liked the location for my visit bc everything was easily walkable. Room was comfortable but a little interesting walking all the way across for bathroom. A few small glitches with electrical probably just bc it’s done recently renovated.
Reviewed on Sep 18, 2026
Top rated hotels for your Great Diamond Island vacation package
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Free Cancellation
6.94 mi from city center
$87 nightly
The price is $95 total per night
$95 total
Oct 18 - Oct 19
Total with taxes and fees
Guests staying at Quality Inn & Suites South Portland enjoy free WiFi in public areas, free newspapers, and a picnic area. If you drive, put free parking to good use. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a vending machine and a garden.
Breakfast included
Pet friendly
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Free Cancellation
7.42 mi from city center
$110 nightly
The price is $120 total per night
$120 total
Oct 18 - Oct 19
Total with taxes and fees
Renovated in 2022, Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel offers a gym, free WiFi in public areas, and coffee in a common area. There's free parking, as well as a free airport shuttle (available 24 hours). The front desk is staffed 24/7 to help with dry cleaning or laundry, and answer any questions about the accommodations. This smoke-free hotel also has a vending machine.
Breakfast included
Free airport shuttle
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Free Cancellation
Reserve now, pay when you stay
4.9 mi from city center
$108 nightly
The price is $119 total per night
$119 total
Oct 18 - Oct 19
Total with taxes and fees
Guests staying at Clarion Hotel Portland Airport ME enjoy an indoor pool, a gym, and free WiFi in public areas. There's free parking, as well as a free airport shuttle (available on request). Multilingual staff at the 24-hour front desk can assist with concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Great Diamond Island
View all propertiesLowest 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.
Things to do
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
90% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
$59
per adult
Explore More Ways to Travel with Travelocity
- Hotels near Gilsland Farm Audubon Center
- Romantic Getaways & Hotels in East Deering
- Hotels near Maine Jewish Museum
- Hotels near East End Beach
- Munjoy Hill Hotels
- Hotels near Portland Observatory
- Hotels with Pool in Long Island
- Long Island Hotels
- Motels in Long Island
- Apartments in Peaks Island
- Hostels in Peaks Island
- Business Hotels in Peaks Island
- Hotels with Hot Tubs in Peaks Island
- Peaks Island Hotels
- Motels in Peaks Island
- Resorts in Peaks Island
- Hotels near Eastern Promenade
- Hotels near Umbrella Cover Museum
- Hotels near Fort Gorges
- Hotels near Richard Boyd Art Gallery
- 5 Star Hotels in East End
- Beach Resorts & in East End
- Boutique Hotels in East End
- Cheap Hotels in East End
- Hotels with Pool in East End
- Luxury Hotels in East End
- Oceanfront Hotels in East End
- Romantic Getaways & Hotels in East End
- Spa Resorts & in East End
- Hotels near Willard Beach
- Hotels near Portland Harbor Museum
- B&B in Portland
- Cottages in Portland
- Hostels in Portland
- Beach Resorts & in Portland
- Boutique Hotels in Portland
- Cheap Hotels in Portland
- Kid Friendly Hotels in Portland
- Hotels with Bar in Portland
- Hotels with Hot Tubs in Portland
- Hotels with an Indoor Pool in Portland
- Oceanfront Hotels in Portland
- Pet Friendly Hotels in Portland
- Romantic Getaways & Hotels in Portland
- Portland Hotels
- Motels in Portland
- Cabin Rentals in South Portland
- Hotels with Free Parking in Downtown Portland
- Downtown Portland Hotels
- Hotels near Casco Bay Lines Ferry Terminal
- Hotels near Southern Maine Community College
- Cheap Hotels in Willard Beach
- Willard Beach Hotels
- Flights from Peaks Island
- Flights from Charlotte to Portland
- Flights from Chicago to Portland
- Flights from Cincinnati to Portland
- Flights from Cleveland to Portland
- Flights from Denver to Portland
- Flights from Detroit to Portland
- Flights from Minneapolis - St. Paul to Portland
- Flights from New Orleans to Portland
- Flights from New York to Portland
- Flights from Philadelphia to Portland
- Flights from Salt Lake City to Portland
- Flights from Portland
- Flights from Newark to Portland
- Flights from Allentown to Portland
- Phippsburg Vacations
- Saco Vacations
- Old Orchard Beach Parasail
- Yarmouth Vacations
- Higgins Beach
- Cumberland Center Vacations
- Seacoast Adventure
- Eartha
- Raymond Vacations
- Frye Island Vacations
- New Gloucester Vacations
- Goose Rocks Beach
- Scarborough Vacations
- Brunswick Vacations
- Cape Elizabeth Vacations
- Old Orchard Beach Pier
- Funtown Splashtown USA
- Charles Q. Clapp House
- Old Orchard Beach Vacations
- Brunswick Golf Course
- Portland Vacations
- South Portland Vacations
- Wyler Gallery
- Gulf of Maine
- Casco Bay
- Windham Vacations
- Biddeford Vacations
- Freeport Vacations
- Georgetown Historical Society
- Biddeford City Theater
- Portland vacation rentals
- Hotels in Old Port
- Oceanfront Hotels in Portland
- Bed & breakfast in Portland
- Motels in Portland
- Hotels in Peaks Island
- Hotels in South Portland
- Car rentals in Portland
- Pet-friendly Hotels in Portland
- Hotels in Downtown Portland
- Hotels with Free Airport Shuttle in Portland
- Flights to Portland
- Hotels in Portland
- Cheap Hotels in Portland
