Long Island Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Long Island Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
17 Oct - 22 Oct
found 7 hours ago
Return flight included
Minneapolis (MSP) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
Perfect location to enjoy old port

Reviewed on 13 Aug, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
per person
17 Oct - 22 Oct
found 7 hours ago
Return flight included
Minneapolis (MSP) to Portland (PWM)
9.6/10 Exceptional! (219 reviews)
Property is modern and clean and a great choice if staying more than one night. The 5:00 check in time is inconvenient and the additional rates for early check in are ridiculous. Our room was ready early even though the information given before check in stated early check in was not available, so we appreciated that. Bed was okay comfort-wise, but the pillows are awful. The biggest gripe I had was being woken by a very loud family with screaming kids well before 7:30 am on a day we looked forward to sleeping in. If this matters to you, the walls and floors are not very soundproof. This was a very unpleasant way to start the second day of a two-day trip. On a positive note, the staff was available via text and responded to our questions quickly and professionally. One suggestion-an exterior sign. The loft was hard to find, with only small signage on the entry doors which is not easily visible from the street. Overall we were happy and would stay again.

Reviewed on 11 Aug, 2025

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Save 100% on your flight
per person
17 Oct - 22 Oct
found 7 hours ago
Return flight included
Minneapolis (MSP) to Portland (PWM)
9.8/10 Exceptional! (114 reviews)
The Blind Tiger was a gem. It was convenient and private enough to enjoy with staff available 24/7 with and questions. The room, lobby and all areas were immaculate and brilliantly arranged. I would definitely go again!

Reviewed on 23 Jul, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
per person
17 Oct - 22 Oct
found 7 hours ago
Return flight included
Minneapolis (MSP) to Portland (PWM)
9.6/10 Exceptional! (149 reviews)
Small bathroom. No safe. No storage space. Everything else was above average.

Reviewed on 16 Jul, 2025

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
Save 100% on your flight
per person
17 Oct - 22 Oct
found 7 hours ago
Return flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (1,004 reviews)
This hotel is centrally located with many dining options in the Old Port area. It also has a nice rooftop bar with nice views. The room was spacious and very pleasant, everything was clean and well taken care of. Great place to stay in Portland!

Reviewed on 10 Aug, 2025

Top hotels in Long Island

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$162 per night from 24 Aug to 25 Aug
S$162
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (1,157 reviews)
"Great value and location."

Reviewed on 12 Aug, 2025

Days Inn by Wyndham Airport/Maine Mall
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is S$136 per night from 24 Aug to 25 Aug
S$136
24 Aug - 25 Aug
includes taxes & fees
7.6/10 Good! (136 reviews)
"Good place."

Reviewed on 12 Aug, 2025

Germaine Inn South Portland
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 S$188 per night from 1 Sept to 2 Sept
S$188
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (1,046 reviews)
"Motel was great the employees were awesome The only thing that was a concern was our patio it was not swept and did not have chairs to sit on"

Reviewed on 11 Aug, 2025

Ramada Plaza by Wyndham Portland
See all 2,518 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.

Frequently asked questions

How much does a Long Island holiday package cost?
You'll find cheap prices from S$1,610 on Expedia for your Long Island getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your holiday to Long Island costs.
What are the cheapest months to go to Long Island?
You can usually find lower prices and better availability in January, February and March. Take a look at our cheap Long Island holiday packages and you could score some great off-season discounts.
How many days is enough for Long Island?
Usually, a handful of days is enough to visit the major attractions during your Long Island holiday. But if you want to have some time to unwind or take day tours, think about extending your itinerary.
How to find the best Long Island package deals?
Use Expedia's filter tool to help you find some fabulous Long Island package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Long Island package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your holiday package as early as possible.
Is it cheaper to book a Long Island holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Long Island holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Long Island?
Score incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Long Island break.
How to plan a trip to Long Island?

  1. Pick your travel dates: What you'd like to do in Long Island and your preferred season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and food to flights and activities. Your accommodation will likely be the largest expense during your trip to Long Island.
  3. Decide how many days away: Start by listing all the activities and sights you'd like to experience in Long Island. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a Long Island holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.