Stockbridge Holidays

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Your Stockbridge Holiday

With a Stockbridge holiday package, say goodbye to endless planning and hello to hassle-free adventure. Every detail of your escape has been taken care of before departing, so you can make the most of your time experiencing this lively city. Eager to venture out and explore? Tanglewood Music Centre, National Shrine of the Divine Mercy and Lee Premium Outlets are three of the best places to visit during your trip to Stockbridge. Your perfect Stockbridge holiday is a couple of clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored just for you.

Stockbridge Essential Information

Language
English
Currency
U.S dollars
Population
2,300
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Norman Rockwell Museum, Ski Butternut and Catamount Ski Area

Our pick of the best Stockbridge Hotel Deals

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 Wi-Fi, 3 restaurants and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,000 reviews)
"I had excellent stay at the Red Lion Inn"

Reviewed on 16 Jun 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 Wi-Fi and free parking. Popular attractions Tanglewood Music Center and Naumkeag Museum are located ...
Like a stay at granny’s house
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, ..."

Reviewed on 19 Feb 2024

Tanglewood Suites
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 centre and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,830 reviews)
"second time stayed here. Love it!"

Reviewed on 20 Jun 2025

Vacation Village in the Berkshires
See all 1,363 properties in Stockbridge
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Stockbridge holiday with Expedia?
Choose Expedia to plan your next big adventure with ease, all in one convenient place. Our insider tip for scoring the best deal on a Stockbridge retreat? Bundle your flights, hotel and/or hire car into a package holiday. Then add a few fun tours and activities. Most bookings also include flexible cancellation policies, so there's no need to worry if you have to switch up your itinerary. Round-the-clock help with cancelling and amending your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Stockbridge?
Stockbridge is at its busiest in February, March and April. If you're hoping for a more relaxed getaway, go there in November, December and January. Organise your escape to Stockbridge according to what type of holiday you want. January is the coolest time of year, when average daytime temperatures are -5ºC. In July, the warmest month, you can expect temperatures of around 21ºC during the day.
What is the top hotel for my holiday in Stockbridge?
Unwind in Stockbridge by choosing Boston Park Plaza as your home base and gateway to adventure and fun.
How do I get a cheap holiday to Stockbridge?
Secure flights that fit your busy schedule, add a hotel room to your booking and watch the savings stack up with a Stockbridge holiday. It's that simple! From hotels and flights to hire cars and tours, Expedia makes travelling cheaply a cinch. And with over 400 airlines and 321,000 hotel options throughout the world to select from, you won't be short of choice. Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Stockbridge holiday?
There are lots of places to visit while on your holiday in Stockbridge. Tanglewood Music Centre, National Shrine of the Divine Mercy, Ski Butternut and Norman Rockwell Museum are some of this city's most popular attractions.
What is the best area to stay in when on holiday in Stockbridge?
There's so much to do in Stockbridge, so stay close to its best attractions and maximise your time sightseeing. National Shrine of the Divine Mercy is one place to put on your itinerary.
Do I need a visa for my Stockbridge holiday?
Look up the latest rules on official government websites. Your nationality and whether you're visiting for study, business or leisure will determine if you'll require a visa for Stockbridge. Make yourself familiar with the application process, including any required documentation, fees and turnaround times. Submit your application well in advance to allow plenty of time for processing. Some visas can take many weeks or even months to obtain, depending on the country.
What should I wear on my Stockbridge holiday?
Consider the activities planned during your holiday in Stockbridge and create a travel wardrobe that you can easily mix and match. For fashion inspiration or information on any dress codes, browse style blogs or relevant social media accounts. Daytime temperatures in January, Stockbridge's coolest month, average around -5ºC. July marks this city's warmest month when the average daily temperature reaches 21ºC. Our tip? Take the guesswork out of what to pack and check the local weather forecast.
What does an Expedia Stockbridge holiday include?
It all comes down to what type of trip you want to have. Stockbridge holiday deals can include car hires, hotels and flights. You can mix and match to create the bundle that suits you. You can also add on activities and experiences after you've booked to get even bigger discounts. Discover a wide range of property types and select one that suits the size of your group. The most in-demand holiday rentals here are private holiday homes and cottages. With Expedia, you can easily design your Stockbridge escape however you like.
Does Expedia offer Book Now, Pay Later Stockbridge holidays?
We do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply pick the payment plan that suits best during the checkout process and take away the stress of budgeting for your next trip. Be sure to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:
  • Pay monthly holidays: Klarna offers the ability to pay in multiple transactions that suit all budgets, so you can jet away on that well-deserved holiday now.
  • No-deposit holidays: When you spot an incredible deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your getaway.

Can I choose my airline with a Stockbridge Expedia holiday?
Yes, you can. Expedia has access to more than 400 partner airlines around the world, so opt for the carrier that best fits your budget and travelling style.

Discover the most popular places to visit in Stockbridge

Norman Rockwell Museum

Norman Rockwell Museum

5/5(1 review)

You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell Museum

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.