Long Island Vacations from $533

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Your Long Island Vacation

The best way to experience this vibrant city is with a customized Long Island vacation package. Base yourself in the neighborhood of Parkside, which is good for festivals, markets and walking or go someplace else — our package deals are all about you. Like to explore your new surroundings? Portland Head Light, Portland Museum of Art and University of Southern Maine are just three of the top places to visit during a trip to Long Island. A couple of clicks is all it takes to build a customized Long Island vacation on Expedia.

The Latest Long Island Vacation Packages

Prices and availability subject to change. Additional terms may apply.
Residence Inn by Marriott Portland Downtown Waterfront

Residence Inn by Marriott Portland Downtown Waterfront

3 out of 5
East Bayside
per person
Jul 8 - Jul 11
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (1,001 reviews)
An outdated property but great location that serves our family purpose and needs. Staff was friendly; although no one really smiled with the exception of the front desk when we inquired to update our key cards. We are not sure if we stay here next time. May need to opt to a newer facility. Pros included pet friendly, pool and free breakfast. My little one did enjoy anll three and all three did put a smile on her face. Cushions on couches were old and didn’t feel clean. We have been frequenting this area for the last 7-8 years and have stayed here each time. Many great family memories but I think we may have outgrown this hotel. We prefer clean and new. Wished the lobby smell was the smell in our room.

Reviewed on Apr 19, 2024

Waldo Emerson Inn

Waldo Emerson Inn

3 out of 5
per person
Jun 28 - Jul 1
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
8.6/10 Excellent! (313 reviews)
Great place to relax and wind down. The innkeepers where excellent.

Reviewed on Oct 28, 2023

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Jun 1 - Jun 4
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9/10 Wonderful! (1,135 reviews)
Loved the spacious rooms and atmosphere

Reviewed on Apr 24, 2024

Hidden Pond

Hidden Pond

4 out of 5
per person
Jun 28 - Jul 1
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
8/10 Very Good! (6 reviews)
White Barn Inn & Spa, Auberge Resorts Collection

White Barn Inn & Spa, Auberge Resorts Collection

5 out of 5
per person
Jun 28 - Jul 1
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
9.6/10 Exceptional! (74 reviews)
Trash outside picture window to forest, under bathroom sink a bit scary, coffee order in morning was never delivered correctly

Reviewed on Apr 13, 2023

Long Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Population
210
Max Temp Winter
30ºF
Max Temp Summer
70ºF
Top Sights
State Theatre, Higgins Beach and East End Beach

Long Island Hotel Deals

Ramada Plaza by Wyndham Portland
Ramada Plaza by Wyndham Portland
3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is $85 per night from Apr 28 to Apr 29
$85
$94 total
includes taxes & fees
Apr 28 - Apr 29
7.4/10 Good! (1,001 reviews)
"Great experience!"

Reviewed on Apr 22, 2024

Ramada Plaza by Wyndham Portland
The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is $178 per night from May 6 to May 7
$178
$202 total
includes taxes & fees
May 6 - May 7
8.4/10 Very Good! (1,060 reviews)
Best location in Portland
"Fantastic (the best for comparable hotels) location. The room can feel dated compared to something like AC hotel, which is on the water but not central. Service is great, the Windows have interesting visitas. Bathrooms are dated and rooms are tighter than comparable."

Reviewed on Apr 18, 2024

The Westin Portland Harborview
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is $161 per night from Apr 28 to Apr 29
$161
$178 total
includes taxes & fees
Apr 28 - Apr 29
9/10 Wonderful! (1,164 reviews)
"The hotel’s decor truly captured the vibe of coastal Maine. Valet parking at the hotel was easy and efficient. Every employee was happy and helpful. I would stay here again."

Reviewed on Apr 23, 2024

Portland Harbor Hotel
See all 2,211 properties in Long Island
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 other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Long Island vacation package cost?
Discover the best of Long Island from just $533. We offer a wonderful selection of hotels, flights and rental cars to suit your budget. You can pick up even more discounts when you add some sightseeing tours to your package.
How do I get a cheap travel package to Long Island?
Imagine all the fun things you could do in Long Island with extra cash in your pocket. Watch your savings stack up when you combine your flights and hotel into a Long Island vacation package. You have plenty of choice with Expedia too. In fact, you can take your pick of over 550 air carriers and 1,000,000 properties throughout the world. Whether you’re taking off with the whole family or traveling on your own, planning a getaway to Long Island is better with a package.
How far in advance should I book my Long Island vacation?
It’s hard to pick the ideal time for airfares, but we usually say the earlier, the better. Most international journeys on Expedia become available up to a year in advance. If you’re unable to do so, don’t fret. Discounted prices occasionally appear within a few weeks of departure dates.
What does an Expedia Long Island travel package include?
Hotels, flights and a reliable car for your road trip adventures. Simply choose your preferred bundle and get access to incredible deals. Once you’ve made your booking, add on a couple of sightseeing tours and watch your savings grow. When it comes to planning your Long Island break, you’re in charge!
What should I know before booking a Long Island travel package?
Our prices are already low. However, you’ll pick up even better deals if you book your flights, hotels and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and loads of choice.
Can I choose my airline with a Long Island Expedia vacation package?
You can, and with over 550 airlines to choose from all over the world, you have plenty of choice. Scroll through the available options and see which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Long Island vacation package?
Yes, you can. We realize life happens, so we’re here to help if you have to make changes to your Long Island vacation package. You may be able to cancel or amend your itinerary at no cost if you’ve booked in the last 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Look up our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

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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.