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Woodstock

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Woodstock Flights as Low as $482

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

American Airlines
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$482 Roundtrip, found 6 days ago
$482
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $482 found 6 days ago
American Airlines
Thu, Sep 10 - Thu, Oct 1
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$484 Roundtrip, found 3 days ago
$484
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Sep 10 from San Diego Intl. to Rutland Southern Vermont Regional, returning Thu, Oct 1, priced at $484 found 3 days ago
American Airlines
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$492 Roundtrip, found 6 days ago
$492
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $492 found 6 days ago
American Airlines
Wed, Sep 9 - Thu, Oct 1
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$494 Roundtrip, found 3 days ago
$494
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Sep 9 from San Diego Intl. to Rutland Southern Vermont Regional, returning Thu, Oct 1, priced at $494 found 3 days ago
JetBlue Airways
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$502 Roundtrip, found 3 hours ago
$502
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $502 found 3 hours ago
JetBlue Airways
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$503 Roundtrip, found 3 hours ago
$503
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $503 found 3 hours ago
American Airlines
Sat, Sep 12 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$504 Roundtrip, found 3 days ago
$504
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Sep 12 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $504 found 3 days ago
JetBlue Airways
Fri, Sep 11 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$506 Roundtrip, found 3 days ago
$506
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Fri, Sep 11 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $506 found 3 days ago
American Airlines
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$507 Roundtrip, found 6 days ago
$507
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $507 found 6 days ago
American Airlines
Sat, Sep 12 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$509 Roundtrip, found 3 days ago
$509
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Sep 12 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $509 found 3 days ago
American Airlines
Fri, Sep 11 - Thu, Oct 1
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$512 Roundtrip, found 3 days ago
$512
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Sep 11 from San Diego Intl. to Rutland Southern Vermont Regional, returning Thu, Oct 1, priced at $512 found 3 days ago
JetBlue Airways
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$513 Roundtrip, found 3 hours ago
$513
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $513 found 3 hours ago
Delta
Thu, Sep 10 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$514 Roundtrip, found 1 day ago
$514
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Sep 10 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $514 found 1 day ago
American Airlines
Wed, Jul 22 - Tue, Jul 28
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$536 Roundtrip, found 6 days ago
$536
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Jul 22 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Jul 28, priced at $536 found 6 days ago
American Airlines
Sat, Sep 12 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$598 Roundtrip, found 2 days ago
$598
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 12 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $598 found 2 days ago
JetBlue Airways
Wed, Jul 22 - Tue, Jul 28
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$836 Roundtrip, found 6 days ago
$836
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Jul 22 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Jul 28, priced at $836 found 6 days 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 September, 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 $482, 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 $482 right now, why wait?

Woodstock Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$481

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! (590 reviews)
"As always - best hotel in Vermont."

Reviewed on Jul 12, 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 breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,010 reviews)
"when we got to the hotel after a long day of travel we found that the bar and restaurant were closed those days of the week so had to buy chips for dinner. we found a cockroach in the room and when we put out the room cleaning notice, nobody came and cleaned. when we had a nice dinner my daughter ..."

Reviewed on Jul 13, 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! (965 reviews)
"Very nice property. Would be great to have coffee in the rooms. Also very limited hot water. Ran out a few times even after a quick shower."

Reviewed on Jul 12, 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! (294 reviews)
"My only complaint is that our television didn't work. And we told the staff member setting up the evening wine and cheese that and she said someone else had also had the problem. We had had a thunderstorm and thought that maybe that was it, and she said she would check in our room while we were gone ..."

Reviewed on Jul 2, 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! (591 reviews)
"So sad to see you were hit badly by the tornado."

Reviewed on Jul 6, 2026

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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 ...
8.6/10 Excellent! (79 reviews)
"The room was perfect and the outside area was fantastic. Located right on a river with a covered bridge that was an easy walk. Had a great conversation with the owner one night on the outside patio with a fire going in the fireplace on the patio. Would definitely stay there again when in the Woodstock ..."

Reviewed on Jul 13, 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 Quechee Gorge Bridge and Billings Park and Trail are located ...
9.2/10 Wonderful! (67 reviews)
"Charming, clean and friendly place!"

Reviewed on Jul 1, 2026

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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 Quechee Gorge Bridge and Billings Park and Trail are located ...
10/10 Exceptional! (49 reviews)
"Very cool space- a lottle unorthodox, but so much the better!"

Reviewed on Mar 16, 2026

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Stay At Jimmy's
See all 2,698 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.