Stockbridge Vacations from $449

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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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $598, price is now $449 per person
$449
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
8.8/10 Excellent! (2,134 reviews)
Clean room/staff friendly. Convince of checking in early 😋

Reviewed on Dec 19, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,085, price is now $711 per person
$711
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Miami (MIA) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on Nov 29, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $696, price is now $505 per person
$505
per person
Feb 8 - Feb 12
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Front desk staff was Pleasant, respectful and most important patient they didnt rush Pan

Reviewed on Dec 24, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Save 100% on your flight
Price was $1,543, price is now $1,125 per person
$1,125
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
7.4/10 Good! (567 reviews)
Nicely decorated for Christmas. Helpful and attentive staff, Lack of heat in some of the public areas like near the library was an issue, but they tried by keeping the fireplace going. As a helpful hint- the fireplace area in the library was drafty and cold. You can go a long way toward fixing this by repairing or replacing that door that leads outside. There’s a 1 inch gap there. Also, while this is an issue, close those 2 inside doors. That works.

Reviewed on Dec 7, 2025

The Clocktower Hotel at Century House, an Ascend Collection Hotel

The Clocktower Hotel at Century House, an Ascend Collection Hotel

2.5 out of 5
Price was $633, price is now $528 per person
$528
per person
Feb 8 - Feb 12
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
8.4/10 Very Good! (1,004 reviews)
Everything was great except we stayed 4 nights and never once was our room cleaned or towels refreshed.

Reviewed on Dec 7, 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

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

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
$177 nightly
The price is $198 total per night from Jan 14 to Jan 15
$198 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Old time charm and hot tub under the stars

Reviewed on Dec 15, 2025

The Red Lion Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $141 total per night from Jan 4 to Jan 5
$141 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (2,179 reviews)
My stay was great with no problems.

Reviewed on Dec 19, 2025

Vacation Village in the Berkshires
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $103 total per night from Jan 4 to Jan 5
$103 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9/10 Wonderful! (1,006 reviews)
The room is so spotless, bathroom is so luxurious! The bed is so soft and sleep very quickly! The staffs are so great! Quick to answer to my questions and my needs. Definitely come back again to stay!

Reviewed on Dec 22, 2025

The Yankee, Trademark Collection by Wyndham
See all 1,347 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 $449 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.

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