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 ₩261,937 per night from Aug 27 to Aug 28
₩261,937
₩354,502 total
Aug 27 - Aug 28
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Food was great!"

Reviewed on Aug 1, 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 ₩372,810 per night from Aug 10 to Aug 11
₩372,810
₩372,810 total
Aug 10 - Aug 11
includes taxes & fees
7.6/10 Good! (16 reviews)
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 ₩543,651 per night from Aug 25 to Aug 26
₩543,651
₩657,664 total
Aug 25 - Aug 26
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 1,368 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

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 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.