Search Cheap Flights to
Woodstock

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Woodstock Flights as Low as $513

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

Delta
Mon, Nov 2 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$513 Roundtrip, found 3 hours ago
$513
Roundtrip
found 3 hours ago
Select Delta flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $513 found 3 hours ago
United
Mon, Nov 2 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$549 Roundtrip, found 6 days ago
$549
Roundtrip
found 6 days ago
Select United flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $549 found 6 days ago
American Airlines
Tue, Oct 20 - Sat, Nov 7
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$553 Roundtrip, found 12 hours ago
$553
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Oct 20 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Sat, Nov 7, priced at $553 found 12 hours ago
United
Mon, Nov 2 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$563 Roundtrip, found 3 hours ago
$563
Roundtrip
found 3 hours ago
Select United flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $563 found 3 hours ago
United
Mon, Nov 2 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$569 Roundtrip, found 3 hours ago
$569
Roundtrip
found 3 hours ago
Select United flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $569 found 3 hours ago
United
Tue, Oct 20 - Sat, Nov 7
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$574 Roundtrip, found 12 hours ago
$574
Roundtrip
found 12 hours ago
Select United flight, departing Tue, Oct 20 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Sat, Nov 7, priced at $574 found 12 hours ago
United
Thu, Oct 29 - Tue, Nov 17
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$574 Roundtrip, found 1 day ago
$574
Roundtrip
found 1 day ago
Select United flight, departing Thu, Oct 29 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Tue, Nov 17, priced at $574 found 1 day ago
United
Tue, Oct 20 - Sat, Nov 7
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$579 Roundtrip, found 12 hours ago
$579
Roundtrip
found 12 hours ago
Select United flight, departing Tue, Oct 20 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Sat, Nov 7, priced at $579 found 12 hours ago
American Airlines
Tue, Oct 20 - Sat, Nov 7
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$584 Roundtrip, found 12 hours ago
$584
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Oct 20 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Sat, Nov 7, priced at $584 found 12 hours ago
United
Mon, Nov 2 - Sat, Nov 21
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$589 Roundtrip, found 5 hours ago
$589
Roundtrip
found 5 hours ago
Select United flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Sat, Nov 21, priced at $589 found 5 hours ago
American Airlines
Mon, Nov 2 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$594 Roundtrip, found 3 hours ago
$594
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $594 found 3 hours ago
United
Mon, Nov 2 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$595 Roundtrip, found 3 hours ago
$595
Roundtrip
found 3 hours ago
Select United flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $595 found 3 hours ago
American Airlines
Mon, Oct 26 - Sun, Nov 8
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$596 Roundtrip, found 4 days ago
$596
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Oct 26 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 8, priced at $596 found 4 days ago
United
Mon, Nov 2 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$599 Roundtrip, found 12 hours ago
$599
Roundtrip
found 12 hours ago
Select United flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $599 found 12 hours ago
American Airlines
Mon, Nov 2 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$604 Roundtrip, found 12 hours ago
$604
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $604 found 12 hours ago
American Airlines
Tue, Oct 20 - Sat, Nov 7
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$609 Roundtrip, found 12 hours ago
$609
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Oct 20 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Sat, Nov 7, priced at $609 found 12 hours ago

Cheap Flights to Woodstock

Fall in love at first flight with your vacation to Woodstock by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Woodstock on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Woodstock, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Woodstock

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Woodstock with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the VSF airport.

What is the cheapest month to fly to Woodstock?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Woodstock are in November, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Woodstock?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Woodstock.

What airport is best to fly into Woodstock?

When you’re planning your trip to Woodstock, convenience is the name of the game. Luckily, Woodstock Lebanon Municipal Airport is nearby so you can deplane and get going on checking off everything on your Woodstock must-do list.

How much are flights to Woodstock?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Woodstock on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $513, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Woodstock?

The trick to saving a stack of cash on your flight to Woodstock? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $513 right now, why wait?

Woodstock Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$607

Last Minute Hotel Deals in Woodstock

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
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! (604 reviews)
"I wouldn’t run back here. It’s a nice hotel in general. The gardens are pretty. Downsides are the facility’s. Outdoor pool area is average. Looks run down. There is no onsite indoor pool, gym, sauna etc , this is over 1 mile away and also is currently under construction. Breakfast was poor for a ..."

Reviewed on Sep 9, 2026

Get rates
Woodstock Inn & Resort
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast in our reviews. Popular attractions ...
9.6/10 Exceptional! (314 reviews)
"The inn and the grounds are beautifully maintained. The room was comfortable, and the restaurant on the premises was convenient but also had a great breakfast, well worth purchasing. The location was also great relative to downtown."

Reviewed on Sep 6, 2026

Get rates
The Jackson
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
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! (991 reviews)
"Lovely room for a quick stay! Staff was so kind and accommodating! 10/10 Highly recommend!"

Reviewed on Sep 7, 2026

Get rates
The Shire Woodstock
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
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 ...
Get rates
On The River Inn
Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road Woodstock VT
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! (611 reviews)
"I would highly recommend staying with Sleep Woodstock Motel. This is the absolutely nicest and comfy motel I have ever been in. I really enjoyed my stay. The staff is brilliantly professional and respectful. Thank you staff! Keep up the great work with the motel! Loved my stay!"

Reviewed on Sep 4, 2026

Get rates
Sleep Woodstock Motel
Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
2709 Woodstock Rd Woodstock VT
Stay at this guesthouse in Woodstock. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Union Arena Community Center and Ottaquechee ...
8.8/10 Excellent! (87 reviews)
"That property is excellent!"

Reviewed on Sep 5, 2026

Get rates
Lincoln Inn & Gallery
The Vesper

The Vesper

3 out of 5
21 Pleasant St Woodstock VT
Stay at this B&B in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Billings Park and Trail and Dana House Museum are located ...
Get rates
The Vesper
Deer Brook Inn

Deer Brook Inn

3 out of 5
4548 W Woodstock Rd Woodstock VT
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and climate control. Popular attractions Ottaquechee River and Union Arena Community Center are ...
10/10 Exceptional! (7 reviews)
"What an amazing place! The room was perfect--comfy bed, luxurious bedding and great amenities. As a guest, you have full access to the living room, dining room and outdoor areas--which includes a fire pit and sauna. Breakfast was delicious with locally sourced products--many from the property itself--including ..."

Reviewed on Aug 27, 2026

Get rates
Deer Brook Inn
See all 2,716 properties in Woodstock
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.