$52 Cheap flights to Town of Olive

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Cheap flights to Town of Olive from $52 One Way, $102 Round Trip

$102 return flights and $52 one-way flights to Town of Olive were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Sep 12 - Wed, Sep 16
RDU
Raleigh
SWF
Newburgh
$102 Roundtrip, found 9 hours ago
$102
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Sat, Sep 12 from Raleigh to Newburgh, returning Wed, Sep 16, priced at $102 found 9 hours ago
Fri, Sep 11 - Mon, Sep 14
CHS
Charleston
SWF
Newburgh
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Sep 11 from Charleston to Newburgh, returning Mon, Sep 14, priced at $107 found 2 days ago
Sat, Sep 12 - Wed, Sep 16
RDU
Raleigh
SWF
Newburgh
$107 Roundtrip, found 9 hours ago
$107
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Sat, Sep 12 from Raleigh to Newburgh, returning Wed, Sep 16, priced at $107 found 9 hours ago
Sat, Sep 12 - Wed, Sep 16
RDU
Raleigh
SWF
Newburgh
$112 Roundtrip, found 9 hours ago
$112
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Sat, Sep 12 from Raleigh to Newburgh, returning Wed, Sep 16, priced at $112 found 9 hours ago
Wed, Sep 23 - Sat, Sep 26
RDU
Raleigh
SWF
Newburgh
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Sep 23 from Raleigh to Newburgh, returning Sat, Sep 26, priced at $117 found 4 days ago
Wed, Sep 23 - Sat, Sep 26
RDU
Raleigh
SWF
Newburgh
$122 Roundtrip, found 4 days ago
$122
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Sep 23 from Raleigh to Newburgh, returning Sat, Sep 26, priced at $122 found 4 days ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
TPANewburghJune 27 to July 4$402
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Town of Olive Accommodation Deals

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St Hunter NY
$169 nightly
The price is $182 total per night from Jul 12 to Jul 13
$182 total
Jul 12 - Jul 13
Total with taxes and fees
Stay at this hotel in Hunter. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
9.2/10 Wonderful! (977 reviews)
"Excellent location! Clean property and REALLY spacious rooms. You’re close to hiking spots as well as cute coffee shops and restaurants."

Reviewed on Jun 23, 2026

Opens in a new windowHunter Lodge, a Bluebird by Lark
SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

2.5 out of 5
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $94 total per night from Jul 1 to Jul 2
$94 total
Jul 1 - Jul 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Highland. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
7.8/10 Good! (1,002 reviews)
"Needed a clean no-frills place to stay during a road trip. Free breakfast, nice staff, clean roadside hotel. Would stay again."

Reviewed on Jun 22, 2026

Opens in a new windowSureStay Plus Hotel by Best Western Highland Poughkeepsie
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
$187 nightly
The price is $209 total per night from Jul 16 to Jul 17
$209 total
Jul 16 - Jul 17
Total with taxes and fees
Book a stay at this luxury holiday park in Saugerties. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9/10 Wonderful! (516 reviews)
"Nice stay with family"

Reviewed on Jun 21, 2026

Opens in a new windowAutoCamp Catskills
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Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$260 nightly
The price is $294 total per night from Jun 28 to Jun 29
$294 total
Jun 28 - Jun 29
Total with taxes and fees
Book a stay at this business-friendly inn in Rhinebeck. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.2/10 Very Good! (905 reviews)
"We thought we were going to be on the historic hotel but instead placed at the conference center which is delemare inn. Didn’t realize there were two properties"

Reviewed on Jun 22, 2026

Opens in a new windowBeekman Arms and Delamater Inn
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 Olive

Finding cheap flights to Town of Olive is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Town of Olive flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Town of Olive through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Town of Olive—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Town of Olive flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Town of Olive with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

Frequently asked questions

How much is a flight to Town of Olive?
Last week, prices ranged between $102 and $402 for a round-trip flight to Town of Olive. One-way fares departing from Charleston (CHS) dropped to a low $52.
How to book the cheapest flight to Town of Olive?
With some of the most competitive flight deals around, you can jet for less with Orbitz. The following tips and hints will help you score cheap flights to Town of Olive — and leave you with cash to spare:

  • Depending on where you're taking off from, select the 'Nearby airports' function (located under the departure and arrival form fields). In some instances, other departure points offer more value for money.
  • If your travel plans aren't set in stone, click on the 'Show flexible dates' option to browse flight deals for alternative departure dates. You may find an even better fare.
  • You can also select the 'Show options' link to filter results for your preferred carrier, seating class, nonstop flights and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you want to fly.
  • If you know your travel dates, get booking. Ticket prices usually climb as the departure date nears.
  • Consider bundling your hotels, flights and car rental into a package with Orbitz to save cash.
  • If possible, don't travel in the busy season. Airfares often hit their highest during school breaks, summer and other vacation periods like Thanksgiving and Christmas.

What is the best time to book a flight to Town of Olive?
Purchase your flights to Town of Olive in January. This is the best month for bargain fares, followed by February and August. Snap up cheap flights and make your dream vacation a reality with Orbitz.
What day of the week is the cheapest to book a flight to Town of Olive?
When it comes to cheap fares to Town of Olive, the best days to make a booking are generally Tuesdays, Wednesdays and Saturdays. A fabulous flight deal is just clicks away with Orbitz.
What is the cheapest day of the week to fly to Town of Olive?
If you're after cheap flights to Town of Olive, leave at the start of the week. Orbitz data from 2020 shows Monday is the most affordable day to set off, followed by Tuesday. Saturday has the most expensive fares, so avoid flying on this day and do your bank account a favor.
What is the cheapest month to fly to Town of Olive?
To pick up cheap flights to Town of Olive, you should pack your suitcase and take off in August. Orbitz data has found that this is generally a great month to save a bundle on your airfare. If you're hoping to jet to Town of Olive during June, it's worth remembering that this is the least affordable time of year to travel.
Which airlines allow free cancellation?
Life changes, and we believe your ticket should be able to do the same. That's why Orbitz makes it a cinch to search for fares with free cancellation and no change fees. Just enter your travel details and then choose "Filter by flexible change policies." How's that for easy?
What do I need for the flight to Town of Olive?
From onboard activities to travel basics like a pillow, there are some things a frequent flyer won't leave home without. To ensure you're all set for your adventure, have a read through this handy list:

  • Ensure that you have your travel paperwork and some identification. For international journeys, you'll require your passport. When you book your tickets, always use the same name, birth date and gender as written on your government-issued ID.
  • A properly packed carry-on bag is just the ticket for a great flight experience. Given your flight to Town of Olive is no short hop, take a few snacks and activities to keep you happy. A book, magazine or e-reader will help the hours pass.
  • Plane cabins often get chilly. Even if you're traveling during the height of summer, make sure you take a sweater on board just in case.

How do I get cheap first-class/business deals to Town of Olive?
If you think a first or business-class ticket is out of your price range, think again. Here are just a few tips to help you find a premium flight to Town of Olive for a whole lot less:

  • Be more flexible with your travel dates and hold out for deals on business or first-class airfares.
  • Look for a low-cost airline that offers seats in business class. They often come with more legroom and a glass of bubbly — but without the high price.
  • Bid for an upgrade in online auctions or upgrade your seat with points earned through loyalty programs.

What is the best time to go to Town of Olive?
Town of Olive is a fantastic getaway destination year-round, but the most popular months are April, August and November. If you're into warmer weather, consider heading there during the summer. Like most destinations in the Northern Hemisphere, the summer season commences June 20. Temperatures usually range between 55 ºF and 80 ºF during the day.

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.