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Woodstock

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Woodstock Flights as Low as $275

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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 February, 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 $275, 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 $275 right now, why wait?

Woodstock Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$275

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! (558 reviews)
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 2025

Woodstock Inn & Resort
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! (891 reviews)
The staff was super nice and flexible! Location was great

Reviewed on Dec 13, 2025

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 a fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,002 reviews)
Nice experience. Great location, good property, excellent service and care taking

Reviewed on Dec 23, 2025

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 ...
9.4/10 Exceptional! (548 reviews)
The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure.

Reviewed on Dec 4, 2025

Sleep Woodstock Motel
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! (255 reviews)
The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing.

Reviewed on Dec 13, 2025

The Jackson
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! (51 reviews)
Clean, very comfortable & spacious room (SOTO). Very friendly, welcoming host & staff. Our jacuzzi tub's jets were not working. We would have appreciated knowing that in advance.

Reviewed on Dec 16, 2025

The Vesper
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! (57 reviews)
The Lincoln Inn was in a great area outside of Woodstock. The grounds are beautiful, and a covered bridge is only a short walk from the property. The rooms were very clean and comfortable.

Reviewed on Oct 19, 2025

Lincoln Inn & Gallery
Stay At Jimmy's

Stay At Jimmy's

3 out of 5
45 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 Red Wagon Toy Company are located ...
10/10 Exceptional! (46 reviews)
This property is conveniently located with on site parking. It is about 10 mins walk into downtown, there are restaurants, coffee shops and ice cream shops. Room was great, everything you needed was thought of. I would recommend it very much.

Reviewed on Oct 20, 2025

Stay At Jimmy's
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.