Long Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
- Rest easyPlan, book, and manage your trip all in one place
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
CA $831
per person
Nov 20 - Nov 24
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,864 reviews)
This was our favorite hotel on our trip. The property is very clean and well maintained. The restaurant food was delicious. Valet service was great. Location in town was perfect very close to shopping and activities.
Reviewed on Oct 15, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
CA $1,101
per person
Nov 20 - Nov 24
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (400 reviews)
Amazing location and lots of space in Portland Maine. We loved it!!
Reviewed on Oct 14, 2026
Ready to book your vacation to Long Island?
Long Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
CA $118
CA $131 total
Nov 1 - Nov 2
includes taxes & fees
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
CA $163
CA $181 total
Nov 16 - Nov 17
includes taxes & fees
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
CA $126
CA $140 total
Oct 29 - Oct 30
includes taxes & fees
8.2/10 Very good! (1,021 reviews)
"Basic room...comfy bed....sauna and whirlpool area was nice....small very basic gym area but ok...nice grab and bag breakfast small but basic and tasty...staff was very nice tried to help with wi fi sign in but my outlook was not operating there....parking ample...close to amenities ie eateries....shopping...and ..."
Reviewed on Oct 15, 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.
Frequently asked questions
How much does a Long Island vacation package cost?
You'll find cheap prices from CA $673 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 vacation to Long Island costs.
What are the cheapest months to go to Long Island?
January, February and March are great times to look for cheap Long Island vacation packages. Opting to travel in quieter periods means you can typically find reduced prices on accommodations and flights.
How many days is enough for Long Island?
With around 2 days, you'll have enough time to experience popular neighbourhoods like Downtown Portland and Old Port during your Long Island vacation. Make sure to also add East End Beach and Eastern Promenade to your must-see list. In the mood for more adventures? Consider exploring outside of Long Island on day trips and tours.
How to find the best Long Island package deals?
Landing a cheap Long Island package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Long Island package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Long Island vacation as a package?
An Expedia vacation package could land you great savings when compared to booking hotels and flights separately. Better still, you can personalize your Long Island getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Long Island?
If you're planning a spontaneous Long Island trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Long Island?
- Choose your dates: The things you plan to do in Long Island and your preferred season will help you decide when to travel.
- Set your budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Long Island. Then, choose a property that fits your budget, whether that's a wallet-friendly stay or a deluxe getaway.
- Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in Long Island. Then, estimate how long you'll need at each, as well as any travel time.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Long Island vacation package that brings all your bookings together.
Explore a world of travel with Expedia
- Family Hotels in Portland
- Resorts in Casco Bay Islands
- Cabin Rentals in Portland
- Cottages in Portland
- Clarion Pointe South Portland
- Freeport Hotels
- Holiday Inn Express Hotel & Suites South Portland by IHG
- Munjoy Hill Hotels
- Beach Hotel Hotels in Old Orchard Beach
- Pet-Friendly Hotels in Great Diamond Island
- Courtyard by Marriott Portland Airport
- Hotels with Free Parking in Portland
- Oceanfront Hotels in Portland
- Motels in Scarborough
- B&B in Portland
- Inn By The Sea
- Hotels near Maine Mall
- Best Western Merry Manor Inn
- Hotels near Thompson's Point
- Downtown Portland Hotels
- Doubletree by Hilton Hotel Portland
- Inn On Peaks Island
- Pet-Friendly Hotels in Portland
- Portland Hotels
- Old Port Hotels
- Comfort Inn South Portland Airport
- Tru by Hilton Portland Airport Area
- Hotels near Cross Insurance Arena
- South Portland Hotels
- Ogunquit Hotels
- Hotels near Portland Intl. Jetport
- Home2 Suites by Hilton Portland Airport
- Beach Hotel Hotels in Portland
- Boutique Hotels in Portland
- Motels in Portland
- Long Creek Hotel by IHG
- Blind Tiger Portland
- Waterpark Hotels in Portland
- Hotels with Free Airport Shuttle in Portland
- Cheap Hotels in Portland
- Peaks Island Hotels
- Cheap Hotels in South Portland
- Quality Inn & Suites South Portland
- Portland Sheraton at Sable Oaks
- Hotels with Kitchenettes in Portland
- Old Orchard Beach Hotels
- Flights from Detroit (DTW) to Portland (PWM)
- Flights from Halifax (YHZ) to Portland (PWM)
- Flights from Calgary (YYC) to Portland (PWM)
- Flights from Montreal (YUL) to Portland (PWM)
- Flights to Great Diamond Island
- Flights from Edmonton (YEG) to Portland (PWM)
- Flights from Ottawa (YOW) to Portland (PWM)
- Flights from Buffalo (BUF) to Portland (PWM)
- Flights from Vancouver (YVR) to Portland (PWM)
- Flights from Portland Intl. Jetport
- Flights from Fredericton (YFC) to Portland (PWM)
- Flights from Toronto (YYZ) to Portland (PWM)
- Flights from Boston (BOS) to Portland (PWM)
- Flights from Moncton (YQM) to Portland (PWM)
- Flights to Portland
- Portland Vacations
- Windham Vacations
- Desert of Maine
- Portland Museum of Art
- East End Beach
- Palace Playland
- Ogunquit Beach
- Marden's Surplus and Salvage
- Ll Bean Flagship Store
- Camp Ellis Beach
- Casco Vacations
- Durham Vacations
- Westbrook Vacations
- Poland Vacations
- Scarborough Vacations
- Bailey Island Vacations
- Old Orchard Beach Pier
- Higgins Beach
- Gooch's Beach
- Scarborough Beach State Park
- Portland Head Light
- Freeport Vacations
- Ocean Park Vacations
- Visit Old Orchard Beach
- Visit Portland
- Popham Beach State Park
- Aquaboggan Water Park
- Visit Ferry Village
- Seashore Trolley Museum
- Old Orchard Beach Vacations
- Visit Old Port
- Maine Mall
- South Portland Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
