Stockbridge Vacations from $450

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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.

The Latest Stockbridge vacation packages

Price found within the past 48 hours. Click for updated prices.
Gideon Putnam Resort And Spa

Gideon Putnam Resort And Spa

4 out of 5
per person
Aug 26 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.6/10 Excellent! (1,007 reviews)
This hotel was beautiful!

Reviewed on Jun 22, 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 10
found 22 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
9.2/10 Wonderful! (34 reviews)
Wonderful property. Exceptional staff. Will be back.

Reviewed on Jun 26, 2025

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 10
found 22 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
No reviews
Hampton Inn Schenectady Downtown

Hampton Inn Schenectady Downtown

2.5 out of 5
Seward Place
per person
Aug 6 - Aug 10
found 22 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
9/10 Wonderful! (915 reviews)
Clean room. Friendly staff.

Reviewed on Jun 24, 2025

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
per person
Aug 6 - Aug 10
found 22 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
8.4/10 Very Good! (662 reviews)
Overall nice clean hotel . Need to update tvs so you can use streaming services. Need to update website about complimentary breakfast and late check out .

Reviewed on Jun 1, 2025

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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

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
$239 nightly
The price is $268 total per night from Jun 30 to Jul 1
$268 total
Jun 30 - Jul 1
Total includes taxes and fees
8.8/10 Excellent! (1,000 reviews)
"Lovely inn, friendly staff in every area. And a fabulous porch. This is the rare old inn that feels modern, too, and it overflows with charm."

Reviewed on Jun 26, 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
$269 nightly
The price is $269 total per night from Jun 29 to Jun 30
$269 total
Jun 29 - Jun 30
Total includes taxes and 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
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
$125 nightly
The price is $139 total per night from Jun 29 to Jun 30
$139 total
Jun 29 - Jun 30
Total includes taxes and fees
8.6/10 Excellent! (1,836 reviews)
"The property was perfect for a getaway. 1 bedroom suite or more with balconies. Non heating Fireplace for aesthetics. The suite was a jack and Jill! Shower, but also a jet tub separate from shower. All dishes and cooking utensils that you needed. You can grill onsite or cook in your suite as take ..."

Reviewed on Jun 24, 2025

Vacation Village in the Berkshires
See all 1,355 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.

Find the Best Stockbridge Vacation Packages

Stockbridge Essential Information

Language
English
Currency
U.S dollars
Population
2,300
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Norman Rockwell Museum, Ski Butternut and Bousquet Ski Area

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Frequently asked questions

How much does a Stockbridge vacation package cost?
You can grab a vacation package to this popular destination from $450 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'd like to score a cheap Stockbridge vacation package, consider planning a trip in November, December and January. You're likely to find better rates on flights and accommodations during these quieter months --- perfect for travelers wishing to save money.
How many days is enough for Stockbridge?
With a well-organized travel plan, you can easily hit the main Stockbridge sights in a few days. But if you prefer to discover hidden spots or go on day tours, think about booking your Stockbridge vacation for longer.
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 busy. Whether you're traveling with the family or planning a trip with friends, a Stockbridge vacation promises a good time 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. Pick your travel dates: What you want to do in Stockbridge and your preferred season will help you decide when to travel.
  2. Budget wisely: On top of the cost of your hotel, you'll need to factor in other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Stockbridge.
  3. Use our trip planning tool to discover Stockbridge: Research every part of your trip to Stockbridge with this handy planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide how long to go for: Now that you're more familiar with Stockbridge, you can work out the perfect length of your vacation. Pull together a draft itinerary and give yourself enough time to cover everything you want to do.
  5. Bundle your airfare and accommodations: After you've settled on your trip dates and duration, book the right Stockbridge vacation package for you.
  6. Add on excursions and experiences: Take a look at our dedicated travel guide to find some incredible things to do in Stockbridge. Book tickets or make reservations in advance to save time and avoid the hassle of looking for activities when you arrive.

Does Expedia offer Book Now, Pay Later Stockbridge vacation packages?
Your Stockbridge trip should be an escape from your busy life, not a reason for money worries. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.