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
The price is CA $206 per night from May 5 to May 6
CA $206
CA $292 total
includes taxes & fees
May 5 - May 6
8.8/10 Excellent! (1,000 reviews)
"Quaint & hospitable!"

Reviewed on Apr. 13, 2025

The Red Lion Inn
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is CA $143 per night from May 1 to May 2
CA $143
CA $159 total
includes taxes & fees
May 1 - May 2
9/10 Wonderful! (573 reviews)
Beautiful & Affordable!
"Excellent experience and gorgeous property! Will stay again next time we visit the Berkshires."

Reviewed on Apr. 27, 2025

Life House Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from May 14 to May 15
CA $148
CA $185 total
includes taxes & fees
May 14 - May 15
9/10 Wonderful! (625 reviews)
"We loved our stay here. The location is beautiful and close to great hiking spots and nice towns . The resort amenities are awesome. The staff was friendly. We’d love to come back"

Reviewed on Apr. 26, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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.

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.

Discover the most popular places to visit in Stockbridge

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