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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 POU 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 , 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  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 Columbia County 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 , 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  right now, why wait?

Woodstock Flight Information
Destination airport
Woodstock
Destination airport IATA code
POU

Last Minute Hotel Deals in Woodstock

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way, Woodstock, NY
Stay at this 4-star hotel in Woodstock. Enjoy free WiFi, free parking, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (193 reviews)
"Beautiful well-appointed room with big windows that made you feel like you were surrounded by nature. The room was spotless as was the bathroom. The balcony offered a view towards the small waterfall with comfortable seating for two. The staff in the reception area were warm and welcoming. The free ..."

Reviewed on Oct 9, 2025

Woodstock Way Hotel
Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY

3 out of 5
141 Tinker Street, Woodstock, NY
Stay at this 3-star B&B in Woodstock. Enjoy free breakfast, free parking, and a garden. Popular attractions The Comeau Property and Woodstock Public Library ...
8.8/10 Excellent! (129 reviews)
"Close to village and convenient to walk around Woodstock"

Reviewed on Sep 30, 2025

Morning Glory B n B Woodstock NY
The Herwood Inn

The Herwood Inn

4.5 out of 5
148 Tinker St, Woodstock, NY
Stay at this 4.5-star luxury guesthouse in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions The Comeau Property and Woodstock ...
9.6/10 Exceptional! (86 reviews)
"Just lovely all around! I loved the attention to detail inside and on the grounds."

Reviewed on Oct 1, 2025

The Herwood Inn
Hotel Dylan

Hotel Dylan

2 out of 5
320 Maverick Rd, Woodstock, NY
Book a stay at this golf motel in Woodstock. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ashokan Rail Trail- Woodstock Dike Trailhead ...
9.4/10 Exceptional! (36 reviews)
"The hotel had a somewhat cool and interesting vibe, but unfortunately it was pretty noisy at night due to the road noise as it’s located right off a highway. The grounds were nice and they had some games out on the lawn, but that was it. There is nothing else around the hotel. It’s an 15 minute or ..."

Reviewed on Oct 12, 2025

Hotel Dylan
The Woodstock Inn on the Millstream

The Woodstock Inn on the Millstream

3 out of 5
48 Tannery Brook Rd, Woodstock, NY
Stay at this 3-star hotel in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions SweetHeart Gallery and Woodstock Artists Association ...
8.8/10 Excellent! (200 reviews)
"Town of Woodstock is very friendly and welcoming."

Reviewed on Oct 9, 2025

The Woodstock Inn on the Millstream
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave, Kingston, NY
Book a stay at this family-friendly hotel in Kingston. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,032 reviews)
"Friendly"

Reviewed on Oct 14, 2025

Best Western Plus Kingston Hotel And Conference Center
Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz

2 out of 5
7 Terwilliger Ln, New Paltz, NY
Book a stay at this business-friendly motel in New Paltz. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,022 reviews)
"Great place for a stay on the way!"

Reviewed on Oct 16, 2025

Americas Best Value Inn New Paltz
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St, Hunter, NY
Stay at this 3-star hotel in Hunter. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.2/10 Wonderful! (784 reviews)
"Lovely overnight stop for us traveling through the Catskills. Love the dark rich lodge colors and decor. Room was big with nice toiletries."

Reviewed on Oct 16, 2025

Hunter Lodge, a Bluebird by Lark
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.