Cheap flights To Woodstock (VSF) from $78

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights to Woodstock from $78 One Way, $155 Round Trip

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

Thu, Jan 28 - Sun, Jan 31
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 14 hours ago
$155
Roundtrip
found 14 hours ago
Select Cape Air flight, departing Thu, Jan 28 from Logan Intl. to Lebanon Municipal, returning Sun, Jan 31, priced at $155 found 14 hours ago
Sat, Jul 25 - Sun, Jul 26
BOS
Logan Intl.
LEB
Lebanon Municipal
$172 Roundtrip, found 10 hours ago
$172
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Sat, Jul 25 from Logan Intl. to Lebanon Municipal, returning Sun, Jul 26, priced at $172 found 10 hours ago
Sat, Jul 25 - Sun, Jul 26
BOS
Logan Intl.
LEB
Lebanon Municipal
$173 Roundtrip, found 10 hours ago
$173
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Sat, Jul 25 from Logan Intl. to Lebanon Municipal, returning Sun, Jul 26, priced at $173 found 10 hours ago
Fri, Oct 9 - Fri, Oct 9
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$174 Roundtrip, found 1 day ago
$174
Roundtrip
found 1 day ago
Select Cape Air flight, departing Fri, Oct 9 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Oct 9, priced at $174 found 1 day ago
Sun, Jul 19 - Thu, Jul 23
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, found 18 hours ago
$175
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Sun, Jul 19 from Logan Intl. to Lebanon Municipal, returning Thu, Jul 23, priced at $175 found 18 hours ago
Sat, Jul 25 - Sun, Jul 26
BOS
Logan Intl.
LEB
Lebanon Municipal
$178 Roundtrip, found 10 hours ago
$178
Roundtrip
found 10 hours ago
Select Cape Air flight, departing Sat, Jul 25 from Logan Intl. to Lebanon Municipal, returning Sun, Jul 26, priced at $178 found 10 hours ago
Sun, Jul 19 - Thu, Jul 23
BOS
Logan Intl.
LEB
Lebanon Municipal
$179 Roundtrip, found 18 hours ago
$179
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Sun, Jul 19 from Logan Intl. to Lebanon Municipal, returning Thu, Jul 23, priced at $179 found 18 hours ago
Fri, Oct 16 - Sun, Oct 18
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 14 hours ago
$180
Roundtrip
found 14 hours ago
Select Cape Air flight, departing Fri, Oct 16 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 18, priced at $180 found 14 hours ago
Sat, Jul 25 - Sun, Jul 26
BOS
Logan Intl.
LEB
Lebanon Municipal
$182 Roundtrip, found 10 hours ago
$182
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Sat, Jul 25 from Logan Intl. to Lebanon Municipal, returning Sun, Jul 26, priced at $182 found 10 hours ago
Mon, Jul 27 - Tue, Aug 4
BOS
Logan Intl.
LEB
Lebanon Municipal
$184 Roundtrip, found 6 hours ago
$184
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Mon, Jul 27 from Logan Intl. to Lebanon Municipal, returning Tue, Aug 4, priced at $184 found 6 hours ago

Woodstock Flight Information

Traveling To
Woodstock
Destination Airport IATA Code
VSF
Number of Airlines Serving
Airlines
Cape Air, JetBlue Airways
Flight Price
$155
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.
Sinclair Inn Bed and Breakfast
4.0-star property

Sinclair Inn Bed and Breakfast

Sep 10 - Sep 14

4 night stay

Orlando (MCO) to Springfield (VSF)

American Airlines • Non-stop roundtrip • Coach
Price was $852, price is now $764 per person
$764
per person
found 1 day ago
The Shire Woodstock
3.0-star property

The Shire Woodstock

Aug 20 - Aug 24

4 night stay

Orlando (MCO) to Springfield (VSF)

JetBlue Airways • Non-stop • Coach

Springfield (VSF) to Orlando (MCO)

Cape Air • Non-stop • Coach
Price was $1,782, price is now $1,451 per person
$1,451
per person
found 1 day ago
Jackson Gore Village, A Vail Resorts Property
3.0-star property

Jackson Gore Village, A Vail Resorts Property

Aug 20 - Aug 24

4 night stay

Orlando (MCO) to Springfield (VSF)

JetBlue Airways • Non-stop • Coach

Springfield (VSF) to Orlando (MCO)

Cape Air • Non-stop • Coach
Price was $978, price is now $888 per person
$888
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Orlando to Woodstock
View all trips

Woodstock

Save money on your flights to Woodstock as well as on hotel and car packages.

 

Free Fees

Snap up cheap Woodstock flights at Orbitz, and pay no booking fees. We also don’t charge fees when your plans change or are cancelled. While you’re there, check out our low fare deals on flights to other locations besides flights to Woodstock.

Everyday Is a Great Day to Save Even More

Get bonus points from Orbitz, the best discount travel planner in the business. Use your Orbitz Visa to take advantage of sales on Woodstock flights, or pile on points by using it for gas, groceries, and other everyday goods and services. Pack your wallet with even more savings using our cutting-edge suite of mobile tools.

Mix and Match

At Orbitz, we turned a great idea from the world of fashion into another way for you to save money. When you shop our low cost tickets on flights to any destination, don’t be afraid to mix and match different airlines for maximum savings on your Woodstock flights air ticket. Save more on air travel every day in every way at Orbitz.

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 $155 and $231 this week. Starting your journey from Boston (BOS)? The lowest one-way tickets started at just $78.
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.