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Woodstock

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Woodstock Flights as Low as $133

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

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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 June, 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 $133, 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 $133 right now, why wait?

Woodstock Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$133

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! (570 reviews)
Excellent!!

Reviewed on Mar 18, 2026

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 ...
9.4/10 Exceptional! (1,001 reviews)
I recommend it nice rooms and area around the property. Convenient for skiing.

Reviewed on Mar 30, 2026

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. ...
The Shire Woodstock
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! (563 reviews)
A good stay, comfortable beds, nice bathroom, keurig didn’t work, dog poop not picked up across the driveway, but a good alternative near an expensive town. Great to allow dogs, just clear some dog owners not so great. Overall, very good.

Reviewed on Mar 30, 2026

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! (277 reviews)
Yes, breakfast was delicious with a good amount of options for all.

Reviewed on Apr 1, 2026

The Jackson
Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 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! (65 reviews)
Very pleasant and comfortable stay, about 20 mins drive to Killington nearby. Room was clean and quiet, and bed was very comfortable. Nice coffee/hot chocolate bar in the lobby but unfortunately not offering breakfast anymore.

Reviewed on Mar 9, 2026

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! (57 reviews)
Uniqueness of rooms, breakfast options and walking distance to so many great spots!

Reviewed on Feb 18, 2026

The Vesper
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! (49 reviews)
Very cool space- a lottle unorthodox, but so much the better!

Reviewed on Mar 16, 2026

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.