Cheap Flights to Woodstock from $90

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How Much Does it Cost To Fly To Woodstock?

The cheapest prices found with in the last 7 days for return flights were $179 and $90 for one-way flights to Woodstock for the period specified. Prices and availability are subject to change. Additional terms apply

Fri, Aug 14 - Sun, Aug 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Aug 14 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Aug 16, priced at $179 found 2 days ago
OriginDestinationTravel DatesFlights From*
DCANorth ClarendonSeptember 17 to September 19$388
JFKNorth ClarendonAugust 21 to August 23$392
PHLNorth ClarendonAugust 22 to August 26$412
TPAWest LebanonAugust 13 to August 19$423
TPANorth ClarendonJuly 8 to July 10$453
PHLWest LebanonJuly 7 to July 14$455
DCAWest LebanonJuly 20 to July 20$479
DENWest LebanonSeptember 3 to September 7$549
CLTWest LebanonSeptember 4 to September 8$592
LAXWest LebanonJuly 12 to July 22$599
EWRNorth ClarendonJune 19 to June 21$613
DENNorth ClarendonJuly 28 to August 2$619
CLTNorth ClarendonJuly 4 to July 9$640
LAXNorth ClarendonJune 24 to June 29$668
EWRWest LebanonAugust 19 to September 24$1,056
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWest LebanonJune 19 to June 26$502
JFKNorth ClarendonJune 19 to June 21$537
EWRNorth ClarendonJune 19 to June 21$613
DCAWest LebanonJune 21 to June 25$644
PHLWest LebanonJune 19 to June 21$772
ATLNorth ClarendonJune 21 to June 25$790
TPAWest LebanonJune 19 to June 21$875
LAXNorth ClarendonJune 19 to June 22$876
EWRWest LebanonJune 20 to July 22$1,324
*Prices include taxes and fees

Woodstock Flight Information

Traveling to
Woodstock
Lowest Price
$179
Number of Airlines Serving
Airlines Serving
JetBlue Airways, Cape Air
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Woodstock Accommodation Deals

Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road Woodstock VT
$133 nightly
The price is $147 total per night from Jun 24 to Jun 25
$147 total
Jun 24 - Jun 25
Total with taxes and fees
Stay at this motel in Woodstock. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
9.6/10 Exceptional! (581 reviews)
"As a dog owner, this was the perfect stay. It is so convenient to have your car right there. The AC worked VERY well and the room was tidy, beautiful, and well kept. Everything worked great and appreciated the coffee in the morning! Just note you may not have great cell service, so knowing your room ..."

Reviewed on Jun 10, 2026

Opens in a new windowSleep Woodstock Motel
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.

Luxury Hotels in Woodstock

On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$211 nightly
The price is $232 total per night from Jul 5 to Jul 6
$232 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,004 reviews)
"Beautiful place to stay"

Reviewed on Jun 12, 2026

Opens in a new windowOn The River Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$509 nightly
The price is $560 total per night from Jun 28 to Jun 29
$560 total
Jun 28 - Jun 29
Total with taxes and fees
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (583 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."

Reviewed on May 22, 2026

Opens in a new windowWoodstock Inn & Resort
Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road Woodstock VT
$133 nightly
The price is $147 total per night from Jun 24 to Jun 25
$147 total
Jun 24 - Jun 25
Total with taxes and fees
Stay at this motel in Woodstock. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
9.6/10 Exceptional! (581 reviews)
"As a dog owner, this was the perfect stay. It is so convenient to have your car right there. The AC worked VERY well and the room was tidy, beautiful, and well kept. Everything worked great and appreciated the coffee in the morning! Just note you may not have great cell service, so knowing your room ..."

Reviewed on Jun 10, 2026

Opens in a new windowSleep Woodstock Motel
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.

Family Friendly Hotels in Woodstock

On The River Inn
Great for families

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$211 nightly
The price is $232 total per night from Jul 5 to Jul 6
$232 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,004 reviews)

Families like: Kids pool, playground, game room, skiing nearby

Travelers say...
"Beautiful place to stay"

Reviewed on Jun 12, 2026

Opens in a new windowOn The River Inn
Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road Woodstock VT
$133 nightly
The price is $147 total per night from Jun 24 to Jun 25
$147 total
Jun 24 - Jun 25
Total with taxes and fees
Stay at this motel in Woodstock. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
9.6/10 Exceptional! (581 reviews)
"As a dog owner, this was the perfect stay. It is so convenient to have your car right there. The AC worked VERY well and the room was tidy, beautiful, and well kept. Everything worked great and appreciated the coffee in the morning! Just note you may not have great cell service, so knowing your room ..."

Reviewed on Jun 10, 2026

Opens in a new windowSleep Woodstock Motel
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
$196 nightly
The price is $216 total per night from Jul 8 to Jul 9
$216 total
Jul 8 - Jul 9
Total with taxes and fees
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (935 reviews)
"It was a very comfortable and nice place to stay with a lot of things within walking distance and having it next to the river was fun. They also have bonfires that you can sit by at night. It was a wonderful day."

Reviewed on Jun 10, 2026

Opens in a new windowThe Shire Woodstock
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Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$509 nightly
The price is $560 total per night from Jun 28 to Jun 29
$560 total
Jun 28 - Jun 29
Total with taxes and fees
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (583 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."

Reviewed on May 22, 2026

Opens in a new windowWoodstock Inn & Resort
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.

Best Woodstock Flight and Hotel Packages

Woodstock flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $798, price is now $729 per person
$729
per person
Jul 31 - Aug 3
found 16 hours ago
Roundtrip flight included
New York (JFK) to Springfield (VSF)
Don't see what you're looking for?
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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

Frequently asked questions

Which airlines fly to Woodstock?
Is Woodstock the first destination on your unforgettable world adventure? Wise travelers recommend flying with Cape Air.
What airport is best to fly into Woodstock?
Featuring two airports, you have options when jetting into Woodstock. Bear in mind where you'll be basing yourself and spending a lot of your time, as this may help you settle on which flights you purchase. Lebanon Municipal Airport (LEB) is 10 mi from the sights and sounds of downtown, while RUT is 20 mi away.
Where to stay in Woodstock
Whether you'd like to splash some cash on accommodations or you just want someplace to use as a base, you'll find it in Woodstock. With 272 properties listed on Travelocity, you'll have no issues catching those Zs after a long day of incredible adventures.After a long day of exploring, nothing beats coming home to a luxurious room. The The Jackson House Inn and the 506 On the River Inn are the top upmarket properties to consider in Woodstock. If you'd prefer to spend your vacation budget on amazing Woodstock experiences, make a booking at the Braeside Lodging or the Sleep Woodstock Motel.
Places to visit in Woodstock
Relish in the feeling of your blood pumping as you snowboard down the fluffy snow at Suicide Six Ski Area. Like some more ideas? If you're mad about golf and wouldn't mind playing a quick round, make your way to Woodstock Country Club. But that's not all there is. Head to Billings Farm and Museum if you've tried all the well-known museums and you're hungry for more!
How to get through airport security fast when traveling to Woodstock
Your journey to Woodstock kicks off as soon as you've satisfied all the security checks. Here is a list of helpful tips and hints to make sure you get through quickly:

  • Airport security staff will request to see your boarding pass and travel ID upon arrival. Tuck them away in an accessible place, ready for inspection.
  • You'll need to stop the tunes for a few minutes. Headphones must be taken off and placed in a tray for X-raying. The same goes for items such as heavy jackets and belts.
  • Electronic devices such as phones, laptops and cameras need to be put through the X-ray machine separately. Make sure they're easily accessible.
  • When it comes to traveling with gels or liquids, each passenger is allowed a quart-sized clear zip-lock bag to keep containers no bigger than 3.4 ounces (100 milliliters).
  • Think about the type of footwear you want to travel in. Slippers are great because they're easy to step out of when you're at the security checkpoint. Try wearing a pair on your next flight!
  • Some places have stringent quarantine laws. Consider where you're headed to and whether or not you're permitted to fly with fresh fruit.

Plane Tickets To Woodstock

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Woodstock. Browse through our inventory to explore a wide range of cheap flights to Woodstock to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Woodstock as you anxiously await to exit the plane and explore what Woodstock has to offer. Considering all the amazing local food and culture in Woodstock, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Woodstock to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Woodstock without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Woodstock with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Woodstock today!

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.