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Woodstock

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Woodstock Flights as Low as $461

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

JetBlue Airways
Thu, Mar 26 - Sun, Apr 5
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$461 Roundtrip, found 2 days ago
$461
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sun, Apr 5, priced at $461 found 2 days ago
JetBlue Airways
Thu, Mar 26 - Sun, Apr 5
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$471 Roundtrip, found 2 days ago
$471
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sun, Apr 5, priced at $471 found 2 days ago
JetBlue Airways
Fri, Mar 27 - Mon, Apr 6
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$481 Roundtrip, found 11 hours ago
$481
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Fri, Mar 27 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 6, priced at $481 found 11 hours ago
JetBlue Airways
Thu, Mar 26 - Sun, Apr 5
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$486 Roundtrip, found 2 days ago
$486
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sun, Apr 5, priced at $486 found 2 days ago
Delta
Thu, Mar 26 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$491 Roundtrip, found 7 hours ago
$491
Roundtrip
found 7 hours ago
Select Delta flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $491 found 7 hours ago
JetBlue Airways
Wed, Mar 25 - Sat, Apr 4
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$492 Roundtrip, found 7 hours ago
$492
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sat, Apr 4, priced at $492 found 7 hours ago
Delta
Fri, Mar 27 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$501 Roundtrip, found 7 hours ago
$501
Roundtrip
found 7 hours ago
Select Delta flight, departing Fri, Mar 27 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $501 found 7 hours ago
Delta
Thu, Mar 26 - Mon, Apr 6
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$501 Roundtrip, found 7 hours ago
$501
Roundtrip
found 7 hours ago
Select Delta flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 6, priced at $501 found 7 hours ago
Delta
Wed, Mar 25 - Mon, Apr 6
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$502 Roundtrip, found 7 hours ago
$502
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 6, priced at $502 found 7 hours ago
JetBlue Airways
Thu, Mar 26 - Sun, Apr 5
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$507 Roundtrip, found 2 days ago
$507
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sun, Apr 5, priced at $507 found 2 days ago
Delta
Fri, Mar 27 - Mon, Apr 6
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$511 Roundtrip, found 7 hours ago
$511
Roundtrip
found 7 hours ago
Select Delta flight, departing Fri, Mar 27 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 6, priced at $511 found 7 hours ago
Delta
Thu, Mar 26 - Fri, Apr 3
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$512 Roundtrip, found 7 hours ago
$512
Roundtrip
found 7 hours ago
Select Delta flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Fri, Apr 3, priced at $512 found 7 hours ago
Delta
Wed, Mar 25 - Fri, Apr 3
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$513 Roundtrip, found 7 hours ago
$513
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Fri, Apr 3, priced at $513 found 7 hours ago
American Airlines
Thu, Mar 26 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$516 Roundtrip, found 3 days ago
$516
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $516 found 3 days ago
American Airlines
Thu, Mar 26 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$518 Roundtrip, found 3 days ago
$518
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $518 found 3 days ago
JetBlue Airways
Sat, Mar 28 - Mon, Apr 6
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$530 Roundtrip, found 7 hours ago
$530
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Sat, Mar 28 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 6, priced at $530 found 7 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 $461, 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 $461 right now, why wait?

Woodstock Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$425

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! (567 reviews)
Amazing restaurant and attentive staff

Reviewed on Mar 4, 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 ...
9.4/10 Exceptional! (1,003 reviews)
The breakfast and staff were AMAZING! Freshly made scrambled eggs, bacon, sausage patties, french toast, waffles, Cabot yogurt with all the fixings, dry cereal, hot oatmeal, breads, muffins, danish, etc. Everything was delicious and well presented as well! Forgot to mention freshly gound coffee! ...

Reviewed on Mar 5, 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. ...
8.8/10 Excellent! (914 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! (274 reviews)
Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,

Reviewed on Mar 7, 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 ...
9.6/10 Exceptional! (559 reviews)
Place was great. Easy and convenient. Friendly staff. Good use of the communal room with lounge and kitchen/bath, W/D, comp coffee/snacks

Reviewed on Mar 4, 2026

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Sleep Woodstock Motel
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

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

Reviewed on Feb 18, 2026

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The Vesper
White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive White River Junction VT
Book a stay at this business-friendly hotel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
7/10 Good! (1,001 reviews)
Conditions of room was nice and roomy, temperature was perfect

Reviewed on Mar 11, 2026

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White River Inn and Suites
See all 2,727 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.