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 ￥27,526 per night from Aug 17 to Aug 18
￥27,526
￥37,350 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"The hotel was very nice, well kept, and clean on the inside and had its characteristic charm. The pool area was gorgeous and very relaxing. We loved the charm and the way the property sprawled around the cute town square. Our room was very spacious, clean and the bed was super soft and comfy. However, ..."

Reviewed on Aug 13, 2025

The Red Lion Inn
Tanglewood Suites

Tanglewood Suites

2.5 out of 5
MA-102, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is ￥39,610 per night from Aug 19 to Aug 20
￥39,610
￥39,610 total
Aug 19 - Aug 20
includes taxes & fees
7.4/10 Good! (18 reviews)
"Bed was quite comfortable and the setting was in a beautiful neighborhood. Excellent proximity to Tanglewood. And host gave exceptional information regarding local eateries and things to do. I would have liked to have known at booking that the owner does not accept credit (as the hotels.com app allows ..."

Reviewed on Aug 11, 2025

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 ￥61,037 per night from Aug 28 to Aug 29
￥61,037
￥73,837 total
Aug 28 - Aug 29
includes taxes & fees
"Very expensive for a small room. My son and I could barely sleep in this remote quiet place. Staffs were very friendly."

Reviewed on Nov 2, 2024

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
See all 1,370 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.

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

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

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 many days is enough for Stockbridge?
Usually, a handful of days is enough to explore the major sights during your Stockbridge vacation. But if you want to have time to kick back or go on day tours, consider extending your itinerary.
Is it worth booking a vacation package to Stockbridge?
Stockbridge is a good vacation destination with attractions like National Shrine of the Divine Mercy among the many things to keep you entertained. Whether you're traveling with the family or getting away with friends, a Stockbridge vacation promises fun for everyone.
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.

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