
Long Island Vacation Packages
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- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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
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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.

Portland Harbor Hotel
Downtown Portland
Price was CA $1,547, price is now CA $1,346 per person
CA $1,346
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
We could have moved right in and been happy for life. Flawless.
Reviewed on Mar 30, 2026

Blind Tiger Portland - Danforth Street.
West End
Price was CA $2,026, price is now CA $1,788 per person
CA $1,788
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!
Reviewed on Mar 10, 2026

The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $1,721, price is now CA $1,541 per person
CA $1,541
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
So spacious, decor is modern yet warm. Staff super friendly and helpful. Perfect location for concerts at Merrill, short walk.
Reviewed on Mar 28, 2026

Portland Regency Hotel & Spa
Downtown Portland
Price was CA $1,502, price is now CA $1,377 per person
CA $1,377
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,599 reviews)
Very nice hotel, located in the center of Portland. Will stay there again.
Reviewed on Apr 1, 2026

Kennebunkport Captains Collection
Price was CA $1,455, price is now CA $1,351 per person
CA $1,351
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (686 reviews)
Historic, cozy, and charming mansions and rooms...our stay was amazing.
Reviewed on Mar 15, 2026
Long Island Hotel Deals

The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Apr 26 to Apr 27
CA $158
CA $175 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
Breakfast was really good, free shuttle to town helped, the only problem was the bad was too small, but the rest was really good.
Reviewed on Mar 29, 2026

Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
The price is CA $109 per night from Apr 29 to Apr 30
CA $109
CA $120 total
Apr 29 - Apr 30
includes taxes & fees
8/10 Very Good! (1,409 reviews)
Everything was good except be nice if they didn’t charge for breakfast
Reviewed on Mar 31, 2026

Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Apr 5 to Apr 6
CA $159
CA $229 total
Apr 5 - Apr 6
includes taxes & fees
9.2/10 Wonderful! (1,767 reviews)
We could have moved right in and been happy for life. Flawless.
Reviewed on Mar 30, 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.
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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.







