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
$996
per person
Nov 3 - Nov 10
found 15 hours ago
Roundtrip non-stop flight included
Appleton (ATW) 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 Cross Insurance Arena and Thompson's Point are located nearby.
Evalina Hotel
Downtown Portland
$1,500
per person
Nov 3 - Nov 10
found 15 hours ago
Roundtrip non-stop flight included
Appleton (ATW) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
Blind Tiger Portland – Carleton Street
West End
$1,369
per person
Nov 3 - Nov 10
found 15 hours ago
Roundtrip non-stop flight included
Appleton (ATW) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Thompson's Point and Maine Mall are located nearby.
Beautiful place
Reviewed on Sep 20, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
$1,338
per person
Nov 3 - Nov 10
found 15 hours ago
Roundtrip non-stop flight included
Appleton (ATW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Thompson's Point and Portland Head Light are located nearby.
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
The Docent's Collection at 178 Middle Street
Downtown Portland
$1,327
per person
Nov 3 - Nov 10
found 15 hours ago
Roundtrip non-stop flight included
Appleton (ATW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
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
Blind Tiger Portland - Danforth Street.
West End
$1,623
per person
Nov 3 - Nov 10
found 15 hours ago
Roundtrip non-stop flight included
Appleton (ATW) 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.
Place was charming and quirky. Very comfortable and well located.
Reviewed on Sep 18, 2026
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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 2484 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
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 ...
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 ...
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 ...
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 ...
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 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 ...
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 ...
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 ...
Inn at St John Portland In-Town
939 Congress St Portland ME
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
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 ...
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 ...
Oceanfront Studio w/ Private Dock in Harpswell!
Harpswell ME
Stay at this apartment in Harpswell. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Mitchell Field and Bailey Island Bridge ...
Embassy Suites by Hilton Portland Maine
1050 Westbrook Street Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
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.
Sat, Jan 9 - Wed, Jan 20
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$179
Roundtrip
found 6 days ago
Tue, Nov 10 - Tue, Nov 17
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$219
Roundtrip
found 6 days ago
Tue, Nov 10 - Tue, Nov 17
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$227
Roundtrip
found 6 days ago
Tue, Nov 10 - Tue, Nov 17
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$227
Roundtrip
found 6 days ago
Tue, Nov 10 - Tue, Nov 17
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$277
Roundtrip
found 6 days ago
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