Cheap Flights to Woodstock from $79

How Much Does it Cost To Fly To Woodstock?

The cheapest prices found with in the last 7 days for return flights were $135 and $79 for one-way flights to Woodstock for the period specified. Prices and availability are subject to change. Additional terms apply

Sat, Jan 9 - Sun, Jan 10
BOS
Logan Intl.
LEB
Lebanon Municipal
$135 Roundtrip, found 4 days ago
$135
Roundtrip
found 4 days ago
Select Cape Air flight, departing Sat, Jan 9 from Logan Intl. to Lebanon Municipal, returning Sun, Jan 10, priced at $135 found 4 days ago
OriginDestinationTravel DatesFlights From*
DCAWest LebanonOctober 28 to October 29$334
JFKWest LebanonDecember 1 to December 7$482
DCANorth ClarendonDecember 29 to January 2$502
JFKNorth ClarendonOctober 30 to November 2$505
PHLWest LebanonOctober 22 to October 29$515
PHLNorth ClarendonOctober 31 to November 4$519
EWRWest LebanonOctober 18 to October 18$525
EWRNorth ClarendonNovember 20 to November 23$525
LAXWest LebanonNovember 15 to November 19$608
TPANorth ClarendonDecember 12 to December 19$620
CLTWest LebanonOctober 28 to November 2$620
LAXNorth ClarendonOctober 17 to October 23$654
ATLNorth ClarendonOctober 12 to October 14$683
TPAWest LebanonDecember 18 to December 23$685
DENNorth ClarendonOctober 24 to October 30$701
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWest LebanonOctober 3 to October 7$536
ATLWest LebanonOctober 2 to October 9$785
TPAWest LebanonOctober 2 to October 10$845
*Prices include taxes and fees

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
$143 nightly
The price is $157 total per night from Oct 27 to Oct 28
$157 total
Oct 27 - Oct 28
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! (623 reviews)
"This place is amazing! Keyless check-in and entry was a breeze. Will stay again. Loved it!"

Reviewed on Sep 24, 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
$257 nightly
The price is $283 total per night from Oct 27 to Oct 28
$283 total
Oct 27 - Oct 28
Total with taxes and fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,004 reviews)
"It’s over priced for a hotel requires us to drive to Woodstock and its restaurants and amenities. Although it was not full we were allocated a room at far end of the hotel where WiFi was poor and the room was a bit smaller because stairway next to the room took out part of the space.The pool and ..."

Reviewed on Sep 26, 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
$709 nightly
The price is $780 total per night from Oct 27 to Oct 28
$780 total
Oct 27 - Oct 28
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. ...
Opens in a new windowWoodstock Inn & Resort
Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road Woodstock VT
$143 nightly
The price is $157 total per night from Oct 27 to Oct 28
$157 total
Oct 27 - Oct 28
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! (623 reviews)
"This place is amazing! Keyless check-in and entry was a breeze. Will stay again. Loved it!"

Reviewed on Sep 24, 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
$257 nightly
The price is $283 total per night from Oct 27 to Oct 28
$283 total
Oct 27 - Oct 28
Total with taxes and fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,004 reviews)

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

Travelers say...
"It’s over priced for a hotel requires us to drive to Woodstock and its restaurants and amenities. Although it was not full we were allocated a room at far end of the hotel where WiFi was poor and the room was a bit smaller because stairway next to the room took out part of the space.The pool and ..."

Reviewed on Sep 26, 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
$143 nightly
The price is $157 total per night from Oct 27 to Oct 28
$157 total
Oct 27 - Oct 28
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! (623 reviews)
"This place is amazing! Keyless check-in and entry was a breeze. Will stay again. Loved it!"

Reviewed on Sep 24, 2026

Opens in a new windowSleep Woodstock Motel
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
$336 nightly
The price is $370 total per night from Oct 27 to Oct 28
$370 total
Oct 27 - Oct 28
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! (996 reviews)
"We loved everything about this hotel. It was a short walk to get downtown. Rooms were very clean. We loved the different areas for coffee so we didn’t have to walk too far in the morning."

Reviewed on Sep 26, 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
$709 nightly
The price is $780 total per night from Oct 27 to Oct 28
$780 total
Oct 27 - Oct 28
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. ...
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.
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Price was $852, price is now $793 per person
$793
per person
Oct 28 - Oct 31
found 12 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,653, price is now $1,380 per person
$1,380
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $933, price is now $859 per person
$859
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Don't see what you're looking for?
See all available trips from Orlando to Woodstock
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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.

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