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Stockbridge Vacations

Got your plane ticket booked and paid for and your suitcase packed and ready to go? Read on for a few basic Stockbridge tips before you jet off.

Stockbridge lies 110 miles (177 kilometers) to the north of New York, a significant city.

The population of this area of The Berkshires is around 2,000.

Hotels in Stockbridge

Whether you're in Stockbridge on a family break, a solo adventure or something else entirely, we're confident you'll find the perfect place to hit the hay. Travelocity offers no less than 37 accommodations within easy reach of the downtown area.

It's time for your vacation! Why not indulge in a couple of nights of luxury? If you want first-class service and silky soft sheets, book the Blantyre (16 Blantyre Rd) or the Hampton Terrace Inn (91 Walker Street). If you're the sort of traveler who would rather spend all their time out and about, a lavish suite may not be for you. Some fantastic budget options are the Gateways Inn & Restaurant (51 Walker St) and The Briarcliff Motel (506 Stockbridge Road).

Places to visit in Stockbridge

Consider yourself an art aficionado? Take in inspiring works and discover the story behind them at Norman Rockwell Museum. Seeking some more ideas? It's difficult to see how generations past survived at home without all the modernized equipment we rely on today. Step through the doorway of Naumkeag and learn exactly how they did. But there's more. History is the best teacher. Travel back through the mists of time for an eye-opening lesson at Chesterwood.

Where do you fly into for Stockbridge?

Arriving at Bradley International Airport (BDL)? Once you've disembarked, the center of Stockbridge is approximately 40 miles (64 kilometers) away. Call for a cab and enjoy the ride — your getaway has only just begun!

Frequently asked questions

How much are vacation packages to Stockbridge?
is all you’ll need for an unforgettable vacation in Stockbridge. Bundle your hotel and flights into a Travelocity vacation package and watch how the savings add up. With these kinds of prices, it’s never been more tempting to travel.
How long should my Stockbridge vacation be?
Most travelers secure a hotel for 2 nights in Stockbridge. But that doesn’t mean you have to follow suit. How long you decide to stay all depends on how much you want to see during your vacation. If you’d love to explore every part of this fantastic location, treat yourself to another night or so (or even an extra week!).
Where can I get the best vacation package deals for Stockbridge?
Travelocity is here to help you snap up an unbeatable Stockbridge package deal. With 400 air carriers and 665,000 properties across the globe, you’re sure to find one that works for you.
Why should I purchase my Stockbridge vacation package via Travelocity?
With our Price Match Guarantee, we’ll match any cheaper price you can find. Add to that our 24/7 support and top-quality service and your perfect vacation is closer than ever before.
Will I save money on my Stockbridge car rental if I book it with a hotel or flight?
Combining your flight, hotel and car into a Stockbridge vacation package is the easiest way to score an amazing deal. Plus, having your own wheels gives you absolute freedom to make your way to all those landmarks you’re hoping to see. Sitting 180 kilometersaway from Stockbridge, Broadway is one place that should be on your itinerary. Buckle up and make a day trip of it.
What is the best time of year to go to Stockbridge?
If you’re watching your pennies, is a terrific month to visit, while is the most expensive time of year. is regarded as the peak season. If you’d prefer to avoid the big crowds, tend to be quieter.
Which airport is best for Stockbridge?
Hartford, CT (BDL-Bradley Intl.) is 64 kilometersfrom downtown and is the starting point for many exciting adventures. Alternatively, Albany, NY (ALB-Albany Intl.) is 64 kilometersaway from central Stockbridge and Hartford, CT (HFD-Hartford - Brainard) is 80 kilometersaway from central Stockbridge.
What is there to do in Stockbridge?
Norman Rockwell Museum should be on your to-do list. After you’ve checked off this leading attraction, simply roam through the streets of Stockbridge and experience what makes this fantastic destination tick.
Where should I stay when visiting Stockbridge?
Experience a wonderful world of luxury when you book a room at the Stockbridge Country Inn (4.5 stars) or The Inn at Stockbridge (4.0 stars). Regular travelers to Stockbridge recommend these tempting options.
Can I go on vacation to Stockbridge at this time?
Learn all the info you need to know about travel restrictions and quarantine policies before you head for Stockbridge. Our Covid-19 Travel Advisor is full of useful advice to help make your vacation smooth and hassle-free.