Cheap flights To Woodstock (VSF) from $55

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Cheap Flights to Woodstock from $55 One Way, $133 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Jan 2 - Mon, Jan 5
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$133 Roundtrip, found 5 days ago
$133
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Fri, Jan 2 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jan 5, priced at $133 found 5 days ago
Tue, Dec 30 - Fri, Jan 2
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$135 Roundtrip, found 5 days ago
$135
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Dec 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jan 2, priced at $135 found 5 days ago
Sun, Dec 28 - Fri, Jan 2
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$145 Roundtrip, found 5 days ago
$145
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sun, Dec 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jan 2, priced at $145 found 5 days ago
Thu, Jan 15 - Mon, Jan 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 2 days ago
$155
Roundtrip
found 2 days ago
Select Cape Air flight, departing Thu, Jan 15 from Logan Intl. to Lebanon Municipal, returning Mon, Jan 19, priced at $155 found 2 days ago
Thu, Jan 15 - Mon, Jan 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 2 days ago
$155
Roundtrip
found 2 days ago
Select Cape Air flight, departing Thu, Jan 15 from Logan Intl. to Lebanon Municipal, returning Mon, Jan 19, priced at $155 found 2 days ago
Mon, Dec 29 - Wed, Dec 31
BOS
Logan Intl.
LEB
Lebanon Municipal
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select Cape Air flight, departing Mon, Dec 29 from Logan Intl. to Lebanon Municipal, returning Wed, Dec 31, priced at $157 found 3 days ago
Tue, Jan 6 - Wed, Jan 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$158 Roundtrip, found 3 hours ago
$158
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Tue, Jan 6 from Logan Intl. to Lebanon Municipal, returning Wed, Jan 7, priced at $158 found 3 hours ago
Thu, Jan 15 - Mon, Jan 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Jan 15 from Logan Intl. to Lebanon Municipal, returning Mon, Jan 19, priced at $159 found 2 days ago
Wed, Dec 10 - Wed, Dec 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$289 Roundtrip, found 1 day ago
$289
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Dec 10 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Wed, Dec 10, priced at $289 found 1 day ago
Wed, Dec 10 - Tue, Dec 16
TPA
Tampa Intl.
RUT
Rutland Southern Vermont Regional
$299 Roundtrip, found 4 days ago
$299
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Dec 10 from Tampa Intl. to Rutland Southern Vermont Regional, returning Tue, Dec 16, priced at $299 found 4 days ago

Woodstock Flight Information

Traveling To
Woodstock
Destination Airport IATA Code
VSF
Number of Airlines Serving
Airlines
JetBlue Airways, Cape Air
Flight Price
$133
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Woodstock economy flight packages

Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn
3.0-star property

Deerfield Valley Inn

Dec 20 - Dec 27

7 night stay

Dallas (DFW) to Springfield (VSF)

American Airlines • Roundtrip • Coach
Price was $1,073, price is now $750 per person
$750
per person
found 11 hours ago
The Covered Bridge Inn
2.5-star property

The Covered Bridge Inn

Dec 20 - Dec 27

7 night stay

Dallas (DFW) to Springfield (VSF)

American Airlines • Roundtrip • Coach
Price was $1,019, price is now $773 per person
$773
per person
found 11 hours ago
Latchis Hotel
2.5-star property

Latchis Hotel

Dec 20 - Dec 27

7 night stay

Dallas (DFW) to Springfield (VSF)

American Airlines • Roundtrip • Coach
Price was $981, price is now $797 per person
$797
per person
found 11 hours ago
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Woodstock

Orbitz is your one stop for guaranteed low prices on Woodstock flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

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Orbitz will find you discount air fare for flights to Woodstock and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

Get Free Travel Advice By Calling the Orbitz Hotline

Our experts will make things even easier by helping you to find the best budget flights to Woodstock Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

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Our state of the art mobile apps will allow you to book cheap flights to Woodstock from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

Frequently asked questions

What is the best airport to fly to in Woodstock?
Lebanon Municipal Airport (LEB), around 10 miles east of central Woodstock, is one choice. Rutland Southern Vermont Regional Airport (RUT) will also get you to this city's doorstep. Compare the flight deals to both airports, as well as which terminal is closer to wherever you're staying.
How much is a flight to Woodstock?
Travelers from far and wide landed round-trip deals ranging between $133 and $299 this week. Starting your journey from Boston (BOS)? The lowest one-way tickets started at just $55.
How to book the cheapest flight to Woodstock?
With some of the most incredible flight deals around, bagging a bargain is easy with Orbitz. The following tips and hints will help you find cheap flights to Woodstock — and leave you with more money in your pocket:

  • Consider departing from or arriving at nearby airports to save money. Enter your preferred departure and arrival airports in the form fields, then choose the 'Nearby airports' function below. It will list your options, if any.
  • If your plans aren't written in stone, click on the 'Show flexible dates' option to scan the flight deals for different 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 whether you want to fly in the morning, afternoon or evening under 'Sort & Filter' to the left.
  • If you've sorted your travel dates, don't delay booking your flight. Ticket prices usually climb as the departure date gets closer.
  • Make even more savings on your adventure by bundling your flights, hotels and car rentals into one convenient package deal. Your wallet will thank you for it.
  • If you can, avoid traveling in peak seasons. Airfares are often at their most expensive during school breaks, summer and around other vacation times like Easter, Thanksgiving and Christmas.

What is the best time to book a flight to Woodstock?
Book in January, February or August for the lowest airfares to Woodstock. Once you've found a bargain, buy it — cheap flights are known to appear and vanish at the tap of a button.
What day of the week is the cheapest to book a flight to Woodstock?
To pick up a great flight deal, make a booking on a Tuesday, Wednesday or Saturday. These are usually the cheapest days to book tickets to Woodstock.
What is the cheapest day of the week to fly to Woodstock?
If you're after cheap flights to Woodstock, depart at the start of the week. Orbitz data from 2020 shows Monday is the cheapest day to set off, followed by Tuesday. Saturday has the most expensive fares, so avoid flying on this day and do your wallet a favor.
What is the cheapest month to fly to Woodstock?
To book cheap flights to Woodstock, you should depart in August. If getting a good deal on your ticket is your top priority, Orbitz data has found that this is generally the best month to take a trip. June is when fares are the most expensive.
Which airlines allow free cancellation?
Life changes, and your ticket should be able to do the same. That's why Orbitz makes it a cinch to search for flights with free cancellation and no change fees. Just enter your travel details and then choose "Filter by flexible change policies." How's that for peace of mind?
What do I need for the flight to Woodstock?
There's nothing more enjoyable than flying off on an adventure, but it's good to be prepared. These top tips will help get your trip off to a smooth start:

  • Your travel documents are the most important items you'll need to carry on your flight. To avoid any delays when checking in, make sure that the name on your ticket corresponds with your government-issued photo ID.
  • Take some activities to keep you busy on your journey to Woodstock. Books, magazines and electronic gadgets like laptops and tablets are perfect. Make sure you take a bottle of water with you as well. Even on a short flight, it's important to keep hydrated.
  • It can get chilly on the plane. If you'd rather not shiver your way through the flight, layer up.

How do I get cheap first-class/business deals to Woodstock?
If you think a business or first-class airfare is beyond your reach, you may want to think again. Here are some tips to help you score a premium flight to Woodstock for less:

  • Flexibility is important. By being open to different travel dates, you'll have more chances of landing a great deal on your airfares.
  • Search for a budget carrier that offers seats in business class. They often come with more space and a glass of Champagne — but at a more affordable price.
  • Make the most of your airline's rewards program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in online auctions.

How to get into Woodstock from the airport?
Walk off the plane at Lebanon Municipal Airport (LEB) and then collect the keys from one of two Lebanon Municipal Airport (LEB) car rental outlets on-site, Avis or Hertz. With a sweet set of wheels, getting to the heart of Woodstock from LEB will be a snap. All you have to do is set your GPS and cruise 10 miles to the west. You could also use public transportation or take a taxi into town and rent some wheels directly from the city center. Check out the deals available on our Woodstock car rentals.
What is the best time to go to Woodstock?
There's never a bad time to go to Woodstock, but January, June and August are the liveliest months. As with most of the Northern Hemisphere, the summer season kicks off June 20. If you'd rather get around in a short-sleeved top than a big winter jacket, this time of year may be perfect for you. Expect average daytime highs of 75 ºF and nighttime lows around 50 ºF.

More to Explore

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.