Stockbridge Vacation Packages

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Your Stockbridge Vacation

With a Stockbridge vacation 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 Center, 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 vacation is a couple of clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored just for you.

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Stockbridge Hotel Deals

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from Aug 25 to Aug 26
CA $251
CA $342 total
Aug 25 - Aug 26
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Miranda at the front desk was beyond accommodating. My mom and I enjoyed our stay in this historic hotel!"

Reviewed on Jul. 21, 2025

The Red Lion Inn
Tanglewood Suites

Tanglewood Suites

2.5 out of 5
MA-102, Stockbridge, MA
The price is CA $369 per night from Jul 27 to Jul 28
CA $369
CA $369 total
Jul 27 - Jul 28
includes taxes & fees
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 Feb. 19, 2024

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
The price is CA $591 per night from Jul 30 to Jul 31
CA $591
CA $716 total
Jul 30 - Jul 31
includes taxes & fees
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer ..."

Reviewed on Jul. 27, 2024

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
See all 1,383 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.
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Discover the most popular places to visit in Stockbridge

Norman Rockwell Museum

Norman Rockwell Museum

4.5/5(6 reviews)

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

Norman Rockwell Museum

National Shrine of the Divine Mercy

5/5(1 review)

Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.

National Shrine of the Divine Mercy

Naumkeag Museum

You can spend time browsing the exhibits at Naumkeag Museum during your travels in Stockbridge. While you're in the area, stroll along the lakeside.

Naumkeag Museum

Frequently asked questions

How much does a Stockbridge vacation package cost?
You can grab a vacation package to this top destination on Expedia. However, how much your vacation to Stockbridge costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Stockbridge?
January, February and March are great times to search for cheap Stockbridge vacation packages. Opting to travel in less busy periods means you can usually find lower prices on flights and accommodations.
How many days is enough for Stockbridge?
Generally, a handful of days is enough to check out the top sights during your Stockbridge vacation. However, if you'd like to have time to kick back or go on day trips, consider extending your trip.
Is it worth booking a vacation package to Stockbridge?
Stockbridge offers everything you need for a wonderful escape. Get your Stockbridge vacation off to a flying start by visiting major attractions like National Shrine of the Divine Mercy.
How to find the best Stockbridge package deals?
Finding a cheap Stockbridge package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most affordable Stockbridge package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Stockbridge vacation as a package?
You can enjoy significant savings on your next Stockbridge getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Stockbridge?
Land fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Stockbridge adventure.
How to plan a trip to Stockbridge?

  1. Choose when to get away: Check your schedule and get packing. Your preferred time of year and the available activities will also help you decide when to vacation in Stockbridge.
  2. Budget wisely: On top of the cost of your stay, you should consider other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that may come up during your trip to Stockbridge.
  3. Determine how many days away: Start by listing all the activities and sights you'd like to experience in Stockbridge. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Stockbridge vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.