Long Island Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Long Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
$1,120
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maine Mall and Cross Insurance Arena are located nearby.
Blind Tiger Portland - Danforth Street.
West End
$1,457
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions Thompson's Point and Portland Head Light are located nearby.
Perfect location & beautiful stay! Very unique property. Great recommendations & lovely hospitality. We will definitely come back the next time we’re in Portland!
:)
Reviewed on Aug 23, 2026
The Weldon Hotel
Downtown Portland
$1,260
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Maine Mall and Cross Insurance Arena are located nearby.
The unit was great. The kitchen and it's utensils are excellent.
The turntable record player gives a classic wonderful back in time.
We would suggest more soaking towels under the sink. And keep the corner of the rug not in the living room not slippery.
Other than that it was a wonderfully clean and high end place to stay close to the Old Port.
Reviewed on Aug 24, 2026
Blind Tiger Portland – Carleton Street
West End
$1,303
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions State Theatre and Cross Insurance Arena are located nearby.
Evalina Hotel
Downtown Portland
$1,511
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Thompson's Point and Portland Head Light are located nearby.
Great location! Fun space! Comfortable and clean!
Reviewed on Aug 17, 2026
Portland Regency Hotel & Spa
Downtown Portland
$1,210
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.
The staff was really lovely and helpful. A lovely, very well located historic property. The spa was very nice!
Reviewed on Aug 25, 2026
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See all available trips from Columbus to Long Island
View all tripsLong Island Vacation Packages
Trying to save time and money on your upcoming vacation to Long Island? Well, AARP Travel Center Powered by Expedia® is here to help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Long Island incredible. Our Travel Center is a one-stop shop where you can put together the best vacation package for you. AARP Travel Center has an amazing list of flights and lodgings, and Long Island things to do to pick from.
Long Island Hotels
With 2545 hotels and resorts in Long Island to choose from, you will find one that is perfect for you.
From Long Island hotels with multiple pools and on-site restaurants, to boutique accommodations that add all the thoughtful amenities, you'll get a hotel here that will make your trip one to remember. With AARP Travel Center's Long Island hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.
Things to do in Long Island
Long Island is the perfect spot when you need to get away from it all. With only around 238 people here, this hidden-gem is good for a quite vacation. If you want to take walk through the past, then you are in luck as Long Island has a rich historic district.
If you need more suggestions, then make sure to click on AARP's "Things to Do" tab.
Book Together and Save
As an AARP Member, you get to benefit from all the great deals. You'll save on select hotels worldwide, flights, and even car rentals. No matter what Long Island vacation bundle you choose, you can rest easy knowing that you already saved on your trip. So what are you waiting for? Book today and get ready for your Long Island vacation.
Top Hotel Deals
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's ...
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Comfort Inn South Portland Airport
90 Maine Mall Rd South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Waves Oceanfront Resort
87 W Grand Ave Old Orchard Beach ME
Book a stay at this beach hotel in Old Orchard Beach. Enjoy free parking, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean ...
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
The Westin Portland Harborview
157 High St Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Portland Harbor Hotel
468 Fore Street Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff ...
Spark by Hilton Portland Airport Maine Mall
461 Maine Mall Rd South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Best Western Merry Manor Inn
700 Main St South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sun, Oct 4 - Fri, Oct 9
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$217
Roundtrip
found 2 hours ago
Fri, Oct 30 - Mon, Nov 2
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$222
Roundtrip
found 1 day ago
Tue, Oct 27 - Mon, Nov 2
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$237
Roundtrip
found 4 days ago
Fri, Oct 30 - Mon, Nov 2
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$245
Roundtrip
found 1 day ago
Sat, Sep 26 - Wed, Sep 30
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$257
Roundtrip
found 15 hours ago
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