$257 Cheap flights to Town of Orleans

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Top places to visit in Town of Orleans

A suspension bridge over a calm river, surrounded by dense forest.
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Wellesley Island

Wellesley Island

Cheap flights to Town of Orleans from $257 One Way, $288 Round Trip

$288 return flights and $257 one-way flights to Town of Orleans were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Dec 1 - Tue, Jan 5
RIC
Richmond
ART
Watertown
$288 Roundtrip, found 1 day ago
$288
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Dec 1 from Richmond to Watertown, returning Tue, Jan 5, priced at $288 found 1 day ago
Thu, Nov 5 - Tue, Nov 10
MSY
New Orleans
ART
Watertown
$318 Roundtrip, found 1 day ago
$318
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Nov 5 from New Orleans to Watertown, returning Tue, Nov 10, priced at $318 found 1 day ago
Thu, Nov 5 - Mon, Nov 9
DFW
Dallas
ART
Watertown
$415 Roundtrip, found 6 hours ago
$415
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Thu, Nov 5 from Dallas to Watertown, returning Mon, Nov 9, priced at $415 found 6 hours ago
Wed, Oct 14 - Wed, Oct 21
ATL
Atlanta
ART
Watertown
$479 Roundtrip, found 1 day ago
$479
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Oct 14 from Atlanta to Watertown, returning Wed, Oct 21, priced at $479 found 1 day ago
Sun, Aug 30 - Sun, Sep 6
LGA
New York
ART
Watertown
$486 Roundtrip, found 1 day ago
$486
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Aug 30 from New York to Watertown, returning Sun, Sep 6, priced at $486 found 1 day ago
Sat, Feb 27 - Mon, Mar 1
CHS
Charleston
ART
Watertown
$516 Roundtrip, found 1 day ago
$516
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Feb 27 from Charleston to Watertown, returning Mon, Mar 1, priced at $516 found 1 day ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
ORDDexterAugust 21 to August 24$657
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Town of Orleans Accommodation Deals

Unique Historic Boathouse on a Stunning Private Island in the 1000 Islands

Unique Historic Boathouse on a Stunning Private Island in the 1000 Islands

Fishers Landing NY
Stay at this cottage in Town of Orleans. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Thousand Islands National Park and Boldt Castle are ...
10/10 Exceptional! (5 reviews)
"This boat house is adorable and views are amazing! And I can’t say enough about Ms. Phyllis & Ms Jen! They are wonderful!"

Reviewed on Aug 5, 2026

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Opens in a new windowUnique Historic Boathouse on a Stunning Private Island in the 1000 Islands
Cozy Rustic Cabin - 1000 Islands Getaway

Cozy Rustic Cabin - 1000 Islands Getaway

Wellesley Island NY
Stay at this cabin in Wellesley Island. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Thousand Islands National Park and ...
9.4/10 Exceptional! (13 reviews)
"The cabin was clean and comfortable. While the host communication was exceptional, the cabin does need someone who is checking on it more often opposed to a quick clean, as the toilet broke during our stay, the shower was leaking and the linens are quite old. I wouldn’t blame the hosts, most likely ..."

Reviewed on Aug 17, 2026

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Opens in a new windowCozy Rustic Cabin - 1000 Islands Getaway
Private 4-Acre Retreat • Sleeps 13 • Fire Pit • Playground, 5 min to State Park

Private 4-Acre Retreat • Sleeps 13 • Fire Pit • Playground, 5 min to State Park

Wellesley Island NY
$591 nightly
The price is $656 total per night from Aug 18 to Aug 19
$656 total
Aug 18 - Aug 19
Total with taxes and fees
Stay at this cabin in Wellesley Island. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Boldt Castle and Thousand Islands National ...
10/10 Exceptional! (3 reviews)
"The home is very clean and beautifully decorated. Located near Alex Bay and Clayton yet on a secluded rolling hill with wildflower gardens. Cute coffee nook- enjoyed coffee on deck each morning."

Reviewed on Aug 15, 2026

Opens in a new windowPrivate 4-Acre Retreat • Sleeps 13 • Fire Pit • Playground, 5 min to State Park
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Private Cabin in the Woods-Close to all amenities

Private Cabin in the Woods-Close to all amenities

Wellesley Island NY
Stay at this cabin in Wellesley Island. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Thousand Islands National Park and Boldt Castle ...
10/10 Exceptional! (8 reviews)
"Clean and convenient. Quiet and peaceful location with easy access to 81."

Reviewed on Aug 12, 2026

Get rates
Opens in a new windowPrivate Cabin in the Woods-Close to all amenities
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Town of Orleans

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First-Timers

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Ports and Play

Be sure to check our cruise page for free shore excursions, onboard spending, balcony upgrades and other perks. Orbitz offers last-minute, luxury, weekend and summer cruises. You can even designate which port you want to sail from and pre-book on-shore activities. Get there on the cheap with discounts on flights to Town of Orleans and Town of Orleans flights. Get more bang for your travel buck at Orbitz.

Frequently asked questions

What is the best airport to fly to in Town of Orleans?
Watertown Intl. Airport (ART). It's the city's main airport and is located approximately 15 miles south of the center. You'll be unpacking your belongings and discovering the best of Town of Orleans shortly after flying in.
How much is a flight to Town of Orleans?
Travelers from far and wide scored round-trip bargains ranging from $288 to $657 this week. Arriving from New Orleans (MSY)? The cheapest one-way tickets were $257.
How to book the cheapest flight to Town of Orleans?
With some of the most exciting flight deals around, you'll always get more for your money with Orbitz. The following tips and hints will help you pick up cheap flights to Town of Orleans — and leave you with cash to spare:

  • Consider nearby airports for a better deal. Enter your preferred departure and arrival airports in the form fields, then select the 'Nearby airports' function below. It will show you any available options.
  • If your plans aren't set in concrete, click on the 'Show flexible dates' option to browse flight deals for multiple departure dates. You may find a cheaper fare.
  • To fine tune your results, hit 'Show options.' You can search based on seating class, airlines, nonstop flights and refundable flights. You can also select the time of day you'd like to fly under 'Sort & Filter' to the left.
  • If you know your travel dates, don't wait to book. Prices normally increase as the departure date nears.
  • Think about combining your flights, hotels and car rentals into a package deal with Orbitz to stretch your budget even further.
  • Don't fly during the busy season if possible. By steering clear of school vacations and summer, you can make amazing savings on your airfare.

What is the best time to book a flight to Town of Orleans?
Book in January, February or August for unbeatable fares to Town of Orleans. Once you've tracked down a bargain, snap it up — cheap flights are known to emerge and disappear in an instant.
What day of the week is the cheapest to book a flight to Town of Orleans?
In general, Tuesdays, Wednesdays and Saturdays are the cheapest days of the week to book a flight to Town of Orleans. If you're after the best airfares, search across those days and you could pick up an incredible flight deal.
What is the cheapest day of the week to fly to Town of Orleans?
Think about going early in the week to get cheap flights to Town of Orleans. Orbitz data from 2020 suggests Monday is generally the most affordable day to hop on a plane, followed by Tuesday. Saturday was found to have the highest ticket fares. Presumably, this is because most travelers prefer to begin their trip after a long working week.
What is the cheapest month to fly to Town of Orleans?
We won't keep you in suspense — based on Orbitz data, August is generally the cheapest month to fly. Ideal for those who crave a weekend getaway or just an escape from it all before the weather turns. Be aware that the least affordable time to fly is the height of summer, with fares at their highest in June.
Which airlines allow free cancellation?
If you think your travel plans could change, Orbitz will help you find a flexible ticket. All you have to do is select "Filter by flexible change policies" when searching for your flights. We'll show you all the airlines that include free cancellation within 24 hours and no change fees — along with our famous low prices.
What do I need for the flight to Town of Orleans?
Whether you're familiar with flying or it's your first time in the air, it's always great to be organized on your trip. Here are some things to take into consideration:

  • You'll need to take all applicable travel documents and identification. How much is influenced by where you're flying from. When reserving your ticket, you should always use the same name, gender and birth date as listed on your current ID.
  • A well-packed carry-on bag is just the ticket for flying in comfort. Given your flight to Town of Orleans is no quick hop, take some snacks and things to keep you entertained. Something to read or listen to is sure to help the hours pass.
  • Plane cabins often get quite cool. Even if you're traveling during the peak of summer, make sure you carry some warm clothes to keep comfortable.

How do I get cheap first-class/business deals to Town of Orleans?
There are ways of booking first or business-class tickets to Town of Orleans that won't burn a hole through your budget. Bag a seat at the front of the plane for less with these practical tips:

  • Flexibility is important. By being open to a few travel dates, you'll have more chances of picking up a deal on your airfares.
  • Search for a low-cost carrier that has business-class seats. They often come with extra space and a glass of Champagne — but at a more affordable price.
  • Bid for an upgrade in online auctions or upgrade your fare with points earned through loyalty programs.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.