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Stockbridge

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Stockbridge Flights as Low as $127

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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 ALB 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 November, 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 Pittsfield Municipal 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 $127, 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 $127 right now, why wait?

Stockbridge Flight Information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Roundtrip price
$127

Last Minute Hotel Deals in Stockbridge

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,000 reviews)
"The hotel was very nice, well kept, and clean on the inside and had its characteristic charm. The pool area was gorgeous and very relaxing. We loved the charm and the way the property sprawled around the cute town square. Our room was very spacious, clean and the bed was super soft and comfy. However, ..."

Reviewed on Aug 13, 2025

The Red Lion Inn
Tanglewood Suites

Tanglewood Suites

2.5 out of 5
MA-102, Stockbridge, MA
Stay at this B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Naumkeag Museum are located ...
7.4/10 Good! (18 reviews)
"Bed was quite comfortable and the setting was in a beautiful neighborhood. Excellent proximity to Tanglewood. And host gave exceptional information regarding local eateries and things to do. I would have liked to have known at booking that the owner does not accept credit (as the hotels.com app allows ..."

Reviewed on Aug 11, 2025

Tanglewood Suites
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
"Very expensive for a small room. My son and I could barely sleep in this remote quiet place. Staffs were very friendly."

Reviewed on Nov 2, 2024

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,944 reviews)
"Great location with great amenities. The bed was"

Reviewed on Aug 14, 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (562 reviews)
Rest, relax, and repeat
"Great value for families! The welcoming staff, location (Lenox/Pittsfield border), spacious suite, and ample amenities made for a fantastic vacation. No free breakfast but there are several dining options and markets nearby. Gorgeous view of the sunset from the upper floors. There was a note of upcoming ..."

Reviewed on Aug 14, 2025

Berkshire Mountain Lodge
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,000 reviews)
"Good"

Reviewed on Aug 8, 2025

Quality Inn
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (673 reviews)
"Nice place. Staff was great. Great location."

Reviewed on Aug 13, 2025

Berkshires Untold
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.6/10 Good! (781 reviews)
great place to stay
"Great location and staff was very hospitable. Rooms were spacious with bed and couch. Plenty of parking and nice pool."

Reviewed on Aug 9, 2025

Howard Johnson by Wyndham Lenox
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.