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Woodstock

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Woodstock Flights as Low as $477

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

American Airlines
Thu, Mar 19 - Tue, Mar 24
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$477 Roundtrip, found 22 hours ago
$477
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Thu, Mar 19 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 24, priced at $477 found 22 hours ago
United
Thu, Mar 19 - Tue, Mar 24
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$483 Roundtrip, found 22 hours ago
$483
Roundtrip
found 22 hours ago
Select United flight, departing Thu, Mar 19 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 24, priced at $483 found 22 hours ago
American Airlines
Wed, Mar 18 - Thu, Mar 19
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$491 Roundtrip, found 1 day ago
$491
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Mar 18 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Thu, Mar 19, priced at $491 found 1 day ago
American Airlines
Thu, Mar 19 - Tue, Mar 24
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$492 Roundtrip, found 22 hours ago
$492
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Thu, Mar 19 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 24, priced at $492 found 22 hours ago
Delta
Thu, Mar 19 - Tue, Mar 24
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$502 Roundtrip, found 22 hours ago
$502
Roundtrip
found 22 hours ago
Select Delta flight, departing Thu, Mar 19 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 24, priced at $502 found 22 hours ago
United
Thu, Feb 26 - Tue, Mar 3
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$506 Roundtrip, found 5 hours ago
$506
Roundtrip
found 5 hours ago
Select United flight, departing Thu, Feb 26 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 3, priced at $506 found 5 hours ago
American Airlines
Thu, Mar 19 - Tue, Mar 24
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$506 Roundtrip, found 22 hours ago
$506
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Thu, Mar 19 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 24, priced at $506 found 22 hours ago
United
Thu, Feb 26 - Tue, Mar 3
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$511 Roundtrip, found 5 hours ago
$511
Roundtrip
found 5 hours ago
Select United flight, departing Thu, Feb 26 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 3, priced at $511 found 5 hours ago
Delta
Wed, Mar 18 - Thu, Mar 19
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$511 Roundtrip, found 1 day ago
$511
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Mar 18 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Thu, Mar 19, priced at $511 found 1 day ago
United
Thu, Feb 26 - Tue, Mar 3
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$521 Roundtrip, found 5 hours ago
$521
Roundtrip
found 5 hours ago
Select United flight, departing Thu, Feb 26 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 3, priced at $521 found 5 hours ago
United
Thu, Mar 19 - Tue, Mar 24
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$524 Roundtrip, found 22 hours ago
$524
Roundtrip
found 22 hours ago
Select United flight, departing Thu, Mar 19 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 24, priced at $524 found 22 hours ago
Delta
Thu, Feb 26 - Tue, Mar 3
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$525 Roundtrip, found 1 day ago
$525
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Feb 26 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 3, priced at $525 found 1 day ago
United
Thu, Feb 26 - Tue, Mar 3
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$526 Roundtrip, found 5 hours ago
$526
Roundtrip
found 5 hours ago
Select United flight, departing Thu, Feb 26 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 3, priced at $526 found 5 hours ago
United
Thu, Mar 19 - Tue, Mar 24
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$529 Roundtrip, found 22 hours ago
$529
Roundtrip
found 22 hours ago
Select United flight, departing Thu, Mar 19 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 24, priced at $529 found 22 hours ago
Delta
Thu, Mar 19 - Tue, Mar 24
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$534 Roundtrip, found 22 hours ago
$534
Roundtrip
found 22 hours ago
Select Delta flight, departing Thu, Mar 19 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 24, priced at $534 found 22 hours ago
American Airlines
Thu, Feb 26 - Tue, Mar 3
GSO
Piedmont Triad Intl.
RUT
Rutland Southern Vermont Regional
$537 Roundtrip, found 5 hours ago
$537
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Thu, Feb 26 from Piedmont Triad Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 3, priced at $537 found 5 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 March, 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 $477, 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 $477 right now, why wait?

Woodstock Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$338

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. ...
9.2/10 Wonderful! (564 reviews)
Incredible experience. Can’t wait to return

Reviewed on Feb 13, 2026

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Woodstock Inn & Resort
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 a fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,000 reviews)
The room was clean and the kitchen area was well stocked. The staff is always extremely friendly and helpful. The only thing about the room that could use updating was the carpeting. It was frayed in spots and looked like it needed a refresh!

Reviewed on Feb 12, 2026

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On The River Inn
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. ...
8.6/10 Excellent! (912 reviews)
Great room, lovely view and a wonderful town

Reviewed on Feb 4, 2026

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The Shire Woodstock
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! (263 reviews)
Wonderfully quaint inn converted from 1800's home. Lots of character, common rooms/sitting areas for guests to gather, nice Keurig coffee machine. Stayed in room 27....small but comfortable. Bathroom heat a problem as in no apparent heat? Enjoyed breakfast in dining room. Pricey but excellent quality. ...

Reviewed on Jan 30, 2026

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The Jackson
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 ...
9.4/10 Exceptional! (556 reviews)
Very clean.

Reviewed on Jan 20, 2026

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Sleep Woodstock Motel
Lincoln Inn & Gallery

Lincoln Inn & Gallery

2 out of 5
2709 West Woodstock Rd Woodstock VT
Stay at this inn in Woodstock. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Union Arena Community Center and Ottaquechee ...
8.6/10 Excellent! (62 reviews)
Exceeded our expectations! Cozy, warm, clean vintage room. Easy in front parking, and super friendly and helpful staff. Beautiful views all around the property. Quiet and safe. Proximity perfect to everything in the area, from skiing resort to restaurants, bridges, farmer's markets, and parks. The ...

Reviewed on Feb 9, 2026

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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 ...
9.2/10 Wonderful! (55 reviews)
Huge room with lots of places to sit and read. Even an outside balcony with table and chairs… but at 12* we’re probably not going to be using it !

Reviewed on Dec 29, 2025

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The Vesper
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Book a stay at this ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,003 reviews)
The room was very clean and the bed was comfortable. The staff was friendly and attentive. Temperature was a bit hard to control. The shower never seemed to get HOT. It was warm enough. The thermostat didn’t seem to work. It was as if it was overridden by the establishment. It got quite warm at night ...

Reviewed on Feb 14, 2026

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Killington Mountain Lodge, Tapestry Collection by Hilton
See all 2,733 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.