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Stockbridge

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Stockbridge Flights as Low as $295

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

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Cheap Flights to Stockbridge

Fall in love at first flight with your vacation to Stockbridge 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 Stockbridge on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Stockbridge, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Stockbridge

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Stockbridge 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 Stockbridge?

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 Stockbridge are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Stockbridge?

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 Stockbridge.

What airport is best to fly into Stockbridge?

When you’re planning your trip to Stockbridge, convenience is the name of the game. Luckily, Stockbridge Rutland Southern Vermont Regional Airport is nearby so you can deplane and get going on checking off everything on your Stockbridge must-do list.

How much are flights to Stockbridge?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Stockbridge on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $295, 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 Stockbridge?

The trick to saving a stack of cash on your flight to Stockbridge? 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 $295 right now, why wait?

Stockbridge Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$295

Last Minute Hotel Deals in Stockbridge

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! (1,003 reviews)
Stay at White River Inn
"We had a three day stay. Overall, it was good. Staff was Friendly and helpful. The Pool was extremely cold...but we did it. Selection of Breakfast was minimal...Great Breakfast Staff though. The Hotel needs updating badly. Very worn. Old furniture. sinks don't drain. Floors feel sticky. Bed was comfortable. ..."

Reviewed on Aug 6, 2025

White River Inn and Suites
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
Stay at this 4.5-star 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! (531 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on Jul 30, 2025

Woodstock Inn & Resort
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd, Quechee, VT
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,016 reviews)
"Awesome"

Reviewed on Aug 9, 2025

Align Inn Vermont
Super 8 by Wyndham White River Junction

Super 8 by Wyndham White River Junction

2 out of 5
442 North Hartland Rd, I-91 Exit 11 Rt 5 S 1/4 Mile, White River Junction, VT
Book a stay at this business-friendly motel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
6.2/10 (1,003 reviews)
"Needs some upgrades, but it was a quiet, comfortable stay, will stay again when in the area again."

Reviewed on Jul 30, 2025

Super 8 by Wyndham White River Junction
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (798 reviews)
"Overall we had a comfortable quiet night in a clean room with a good bed and clean bathroom. HOWEVER , we booked a room with river views and found ourselves with views of parking lots. Also the room could use a microwave. And the shower floor was dangerously slippery."

Reviewed on Aug 9, 2025

The Shire Woodstock
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr, Killington, VT
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff ...
8.4/10 Very Good! (1,002 reviews)
"Great place to stay"

Reviewed on Aug 9, 2025

North Star Lodge and Resort
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.2/10 (1,001 reviews)
"Staff was friendly and helpful. Nice breakfast. Comfortable bed. The bathroom needed some maintenance such as new calking around the tub. A little mildew. Ok for one night."

Reviewed on Aug 10, 2025

Days Inn by Wyndham Rutland/Killington Area
Cortina Inn

Cortina Inn

3 out of 5
476 Holiday Drive, Rutland, VT
Stay at this 3-star business-friendly hotel in Rutland. Enjoy free WiFi, free parking, and a free airport shuttle. Popular attractions Green Mountain Shopping ...
6.6/10 (585 reviews)
"So much potential. The parking lot is unkempt, many facilities are shut down, there only seems to be a single staff member on site. The carpets are beaten down, the whole hotel smelled of cleaning agents, and our room smelled of cigarettes. Putting that aside, rooms were actually clean. No bugs, ..."

Reviewed on Aug 8, 2025

Cortina Inn
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.