Long Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Long Island Vacation
An easy way to experience this vibrant city is with a custom-made Long Island vacation package. Stay in the neighborhood of Parkside, which is great for festivals, markets and walking or choose someplace else — our packages are all about you. Sand Beach, Fifth Maine Museum and Little Diamond Island are just some of the sights worth visiting during your trip to Long Island. Whoever you're going away with and whatever your bank balance, your dream Long Island vacation is just a few clicks away with Expedia.
Top Long Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
Price was CA $1,743, price is now CA $1,343 per person
CA $1,343
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,003 reviews)
Great experience all around. Will definitely visit again if in the area.
Reviewed on May 25, 2026
The Meadowmere Resort
Price was CA $2,239, price is now CA $1,672 per person
CA $1,672
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
8.6/10 Excellent! (1,001 reviews)
Clean room , friendly Staff , Breakfast was great !!
Reviewed on May 13, 2026
Cape Arundel Inn and Resort
Price was CA $2,717, price is now CA $2,341 per person
CA $2,341
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (44 reviews)
The room was fantastic and the staff very friendly.
Reviewed on Feb 15, 2026
Long Island Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $295 per night from May 31 to Jun 1
CA $295
CA $379 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,769 reviews)
"An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow."
Reviewed on May 25, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $286 per night from May 31 to Jun 1
CA $286
CA $316 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,657 reviews)
"The place is wonderful. Just remember to get water from the lobby because it is not stocked in the rooms."
Reviewed on May 27, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $237 per night from May 31 to Jun 1
CA $237
CA $300 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,223 reviews)
"We stay here every time we visit our daughter in Portland."
Reviewed on May 27, 2026
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.
Explore a world of travel with Expedia
- B&B in Casco Bay Islands
- Chalets in Casco Bay Islands
- Beach Hotel Hotels in Casco Bay Islands
- Cheap Hotels in Casco Bay Islands
- Hotels with Free Breakfast in Casco Bay Islands
- Luxury Hotels in Casco Bay Islands
- Casco Bay Islands Hotels
- Vacation Homes in Casco Bay Islands
- Resorts in Casco Bay Islands
- Villas in Casco Bay Islands
- Cliff Island Hotels
- Hotels near East End Beach
- Hotels near Eastern Promenade
- Aparthotels in Great Diamond Island
- B&B in Great Diamond Island
- Chalets in Great Diamond Island
- Holiday Park Resorts in Great Diamond Island
- Hostels in Great Diamond Island
- Beach Hotel Hotels in Great Diamond Island
- Cheap Hotels in Great Diamond Island
- Green Hotels in Great Diamond Island
- Hotels with Bar in Great Diamond Island
- Independent Hotels in Great Diamond Island
- Lgbt Friendly Hotels in Great Diamond Island
- Luxury Hotels in Great Diamond Island
- Pet-Friendly Hotels in Great Diamond Island
- Romantic Hotels in Great Diamond Island
- Spa Hotels in Great Diamond Island
- Waterpark Hotels in Great Diamond Island
- Hotel Wedding Venues Hotels in Great Diamond Island
- Great Diamond Island Hotels
- Inns in Great Diamond Island
- Lodges in Great Diamond Island
- Resorts in Great Diamond Island
- Townhomes in Great Diamond Island
- Farmstay in Peaks Island
- B&B in Peaks Island
- Chalets in Peaks Island
- Guest Houses in Peaks Island
- Beach Hotel Hotels in Peaks Island
- Cheap Hotels in Peaks Island
- Golf Hotels in Peaks Island
- Mountain Hotels in Peaks Island
- Peaks Island Hotels
- Motels in Peaks Island
- Portland Hotels
- Hotels near Southern Maine Community College
- Hotels near Spring Point Ledge Lighthouse
- Oceanfront Hotels in Willard Beach
- Willard Beach Hotels
- Flights to Great Diamond Island
- Flights from Atlanta to Casco Bay Islands
- Flights from Boston to Casco Bay Islands
- Flights from Calgary to Casco Bay Islands
- Flights from Denver to Casco Bay Islands
- Flights from London to Casco Bay Islands
- Flights from Montreal to Casco Bay Islands
- Flights from Seattle to Casco Bay Islands
- Flights from Washington to Casco Bay Islands
- Flights from Edmonton to Casco Bay Islands
- Flights from Buffalo to Casco Bay Islands
- Aquaboggan Water Park
- Bailey Island Vacations
- Beech Ridge Motor Speedway
- Casco Bay Islands Vacations
- Visit Casco Bay Islands
- Cousins Island Vacations
- Desert of Maine
- Dunegrass Golf Club
- East End Beach
- Freeport Vacations
- Great Diamond Island Vacations
- Visit Great Diamond Island
- Great Island Vacations
- Higgins Beach
- Ll Bean Flagship Store
- Maine Mall
- Mclellan-Sweat Mansion
- Monkey Trunks Extreme Aerial Adventure Park
- Old Orchard Beach Pier
- Old Orchard Beach Vacations
- Palace Playland
- Pine Point Beach
- Portland Head Light
- Portland Museum of Art
- Portland Vacations
- Scarborough Beach State Park
- Scarborough Vacations
- Shaw Park
- South Portland Vacations
- State Theatre
- Westbrook Vacations
- Windham Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
