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Woodstock

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Woodstock Flights as Low as $430

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

American Airlines
Thu, Nov 19 - Wed, Dec 2
TPA
Tampa Intl.
RUT
Rutland Southern Vermont Regional
$430 Roundtrip, found 18 hours ago
$430
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Thu, Nov 19 from Tampa Intl. to Rutland Southern Vermont Regional, returning Wed, Dec 2, priced at $430 found 18 hours ago
American Airlines
Thu, Nov 19 - Wed, Dec 2
TPA
Tampa Intl.
RUT
Rutland Southern Vermont Regional
$450 Roundtrip, found 18 hours ago
$450
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Thu, Nov 19 from Tampa Intl. to Rutland Southern Vermont Regional, returning Wed, Dec 2, priced at $450 found 18 hours ago
United
Tue, Oct 6 - Wed, Oct 14
DEN
Denver Intl.
LEB
Lebanon Municipal
$479 Roundtrip, found 22 hours ago
$479
Roundtrip
found 22 hours ago
Select United flight, departing Tue, Oct 6 from Denver Intl. to Lebanon Municipal, returning Wed, Oct 14, priced at $479 found 22 hours ago
American Airlines
Tue, Oct 6 - Wed, Oct 14
DEN
Denver Intl.
LEB
Lebanon Municipal
$489 Roundtrip, found 1 day ago
$489
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Denver Intl. to Lebanon Municipal, returning Wed, Oct 14, priced at $489 found 1 day ago
JetBlue Airways
Tue, Sep 22 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$492 Roundtrip, found 1 day ago
$492
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Sep 22 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $492 found 1 day ago
American Airlines
Thu, Nov 19 - Wed, Dec 2
TPA
Tampa Intl.
RUT
Rutland Southern Vermont Regional
$493 Roundtrip, found 18 hours ago
$493
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Thu, Nov 19 from Tampa Intl. to Rutland Southern Vermont Regional, returning Wed, Dec 2, priced at $493 found 18 hours ago
American Airlines
Tue, Oct 6 - Wed, Oct 14
DEN
Denver Intl.
LEB
Lebanon Municipal
$497 Roundtrip, found 1 day ago
$497
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Denver Intl. to Lebanon Municipal, returning Wed, Oct 14, priced at $497 found 1 day ago
American Airlines
Tue, Aug 4 - Wed, Aug 5
DEN
Denver Intl.
RUT
Rutland Southern Vermont Regional
$499 Roundtrip, found 2 days ago
$499
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Aug 4 from Denver Intl. to Rutland Southern Vermont Regional, returning Wed, Aug 5, priced at $499 found 2 days ago
JetBlue Airways
Wed, Sep 23 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$502 Roundtrip, found 1 day ago
$502
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 23 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $502 found 1 day ago
JetBlue Airways
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$503 Roundtrip, found 1 day ago
$503
Roundtrip
found 1 day 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 1 day ago
JetBlue Airways
Fri, Jul 17 - Thu, Jul 23
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$504 Roundtrip, found 22 hours ago
$504
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Fri, Jul 17 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 23, priced at $504 found 22 hours ago
JetBlue Airways
Thu, Jul 23 - Thu, Jul 30
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$505 Roundtrip, found 22 hours ago
$505
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Thu, Jul 23 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 30, priced at $505 found 22 hours ago
American Airlines
Tue, Oct 6 - Wed, Oct 14
DEN
Denver Intl.
LEB
Lebanon Municipal
$507 Roundtrip, found 1 day ago
$507
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Denver Intl. to Lebanon Municipal, returning Wed, Oct 14, priced at $507 found 1 day ago
American Airlines
Sat, Aug 1 - Wed, Aug 5
DEN
Denver Intl.
RUT
Rutland Southern Vermont Regional
$507 Roundtrip, found 2 days ago
$507
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Aug 1 from Denver Intl. to Rutland Southern Vermont Regional, returning Wed, Aug 5, priced at $507 found 2 days ago
JetBlue Airways
Fri, Jul 17 - Thu, Jul 23
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$524 Roundtrip, found 22 hours ago
$524
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Fri, Jul 17 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 23, priced at $524 found 22 hours ago
United
Sat, Sep 12 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$578 Roundtrip, found 4 days ago
$578
Roundtrip
found 4 days ago
Select United flight, departing Sat, Sep 12 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $578 found 4 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 November, 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 $430, 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 $430 right now, why wait?

Woodstock Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$420

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! (588 reviews)
"Had a short stay with my family to the Woodstock Inn and would love to return some day. Hospitality at its best in a beautiful town. The grounds and amenities were immaculate and authentic to the area. A memorable stay."

Reviewed on Jun 25, 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! (1,000 reviews)
"It was beautiful, well designed with plenty of public gathering and relaxing places. The restaurant was excellent for both dinner and breakfast. We loved the coffee bars open all day. Great staff who were very professional and friendly!"

Reviewed on Jun 24, 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! (950 reviews)
"Spent one night here in late June. My room had a gorgeous view of the river out back and was nicely furnished with what looked like antiques (ie four poster bed). My friend and I sat outside in the evening at one of the many fire pits talking and reading. Staff was friendly and helpful. My one wish ..."

Reviewed on Jun 27, 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! (290 reviews)
"The place is absolutely beautiful. The room was very clean and comfortable. We never actually saw a staff person other than the lady serving the 5pm happy hour wine and cheese. She was great. So if you need a staff I’m not really sure how to get in touch with anyone. We would definitely stay there ..."

Reviewed on Jun 27, 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! (586 reviews)
"Free Keurig coffee..small refrigerator had good sized freezer Nice community type room with free snacks and free to use washer dryer"

Reviewed on Jun 26, 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! (75 reviews)
"Two separate buildings with very different feels. Back building has zero area rugs and is super load anytime anyone walks through. Rooms in front building much nicer."

Reviewed on Jun 15, 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 ...
9.4/10 Exceptional! (66 reviews)
"Absolute gem on the edge of.downtown. super walkable everywhere in terms of shopping, and within a 5 min drive to less pricier food options away from downtown. Jessica was an amazing and gracious host. The oatmeal with maple syrup, apples and walnuts was the quintessential Vermont start to the day. ..."

Reviewed on Jun 25, 2026

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The Vesper
Deer Brook Inn

Deer Brook Inn

3 out of 5
4548 W Woodstock Rd Woodstock VT
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and climate control. Popular attractions Ottaquechee River and Union Arena Community Center are ...
10/10 Exceptional! (2 reviews)
"A beautiful location. Hosts were amazing. Clean and tastefully decorated. My only criticism would be to add ports for charging cell phones and computers. Otherwise, it was incredible. We highly recommend this location!"

Reviewed on May 24, 2026

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Deer Brook Inn
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.