Stockbridge Vacations

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Find the Best Stockbridge Vacation Packages

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 AED 509 per night from May 15 to May 16
AED 509
AED 733 total
includes taxes & fees
15 May - 16 May
8.8/10 Excellent! (1,000 reviews)
"Quaint & hospitable!"

Reviewed on 13 April 2025

The Red Lion Inn
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AED 474 per night from Apr 21 to Apr 22
AED 474
AED 529 total
includes taxes & fees
21 Apr - 22 Apr
9/10 Wonderful! (557 reviews)
"The hotel is cozy and charming. The rooms are well-appointed. The staff was great. Easy check-in, check-out. The bar is well stocked and they offer free (real) coffee in the morning!"

Reviewed on 14 April 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 AED 393 per night from Apr 28 to Apr 29
AED 393
AED 491 total
includes taxes & fees
28 Apr - 29 Apr
9/10 Wonderful! (620 reviews)
"Great deal for villa resort suite. Lots of space, great condition, great amenities, great location."

Reviewed on 12 April 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 1,323 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.

Frequently asked questions

How much does a Stockbridge vacation package cost?
You can grab a vacation package to this popular destination on Expedia. However, how much your vacation to Stockbridge costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Stockbridge?
If you’re hoping to snag a cheap Stockbridge vacation package, consider traveling in January, February and March. You’ll usually find lower prices on flights and hotels during these quieter months — perfect for budget-conscious travelers.
How to find the best Stockbridge package deals?
Use Expedia’s filter tool to help you find some terrific Stockbridge package deals. When you begin your search, just set your maximum budget and then sort the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or browse for Stockbridge package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it’s usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Stockbridge vacation as a package?
You can enjoy significant savings on your Stockbridge break by booking a customized vacation package. Click on the “Package” heading, then enter your destination and travel dates to view some great hotel prices and airfares. 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?
Secure amazing discounts by reserving your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Stockbridge trip.
How to plan a trip to Stockbridge?

  1. Choose when to travel: Check your calendar and pack your bags. Your favorite time of year and the type of activities on offer will also help you decide when to escape to Stockbridge.
  2. Set your budget: Factor in expenses such as flights, meals and transportation when calculating how much to put aside for your trip to Stockbridge. Then, choose a hotel that works with your budget, whether that’s an affordable stay or a lavish getaway.
  3. Decide how many days away: Start by compiling a list of the sights and activities you want to get to in Stockbridge. Then, estimate how long you’ll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Stockbridge vacation package.

Discover the most popular places to visit in Stockbridge

Rockwell called his Stockbridge studio, his “best studio yet.” The building was originally located in the backyard of his home on South Street in Stockbridge, Mass. In 1976, toward the end of his life, Rockwell left the studio and its contents to Norman Rockwell Museum. The building was cut in two and moved to the Museum’s grounds in 1986. #Details

Norman Rockwell Museum

4.5/5(193 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

4.5/5(40 reviews)

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

Berkshire Botanical Garden

Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.

Berkshire Botanical Garden