Stockbridge Vacations from $393

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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
Save 100% on your flight
Price was $595, price is now $393 per person
$393
per person
May 4 - May 11
found 18 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (2,134 reviews)
Great! Go annually. Highly recommend

Reviewed on Feb 25, 2026

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $683, price is now $513 per person
$513
per person
Apr 17 - Apr 23
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
8.8/10 Excellent! (1,001 reviews)
Awesome Staff. Great Hotel!

Reviewed on Feb 25, 2026

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
Price was $803, price is now $611 per person
$611
per person
Apr 17 - Apr 23
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
8/10 Very Good! (1,214 reviews)
Nice rooms and large bathroom

Reviewed on Feb 25, 2026

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Price was $980, price is now $756 per person
$756
per person
May 23 - May 25
found 14 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
7.4/10 Good! (567 reviews)
We have been staying at the Equinox for over 35 yrs. Love the whole scene and vibe. Love the pool and hot tub. Love the big real wood fireplace.

Reviewed on Jan 24, 2026

Bluebird Spa City Motor Lodge

Bluebird Spa City Motor Lodge

3 out of 5
Downtown Saratoga Springs
Price was $774, price is now $608 per person
$608
per person
Apr 17 - Apr 23
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9/10 Wonderful! (801 reviews)
I’ve stayed at this location many times. The lodging is perfectly located in the heart of everything. Walking distance to food, shopping, and activities. The lodging itself is affordable, clean, and welcoming. A great place to stay!

Reviewed on Feb 11, 2026

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The Annual Vacation Sale

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Discover the most popular places to visit in Stockbridge

Autumn reflection while walking in the vicinity of Norman Rockwell Museum, Stockbridge. #LivingtheDream #Stockbridge #NewEngland #Reflection #Autumn #Walking

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

National Shrine of the Divine Mercy

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
$201 nightly
The price is $225 total per night from Mar 4 to Mar 5
$225 total
Mar 4 - Mar 5
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
great customer service

Reviewed on Feb 18, 2026

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
$134 nightly
The price is $150 total per night from Mar 29 to Mar 30
$150 total
Mar 29 - Mar 30
Total with taxes and fees
8.8/10 Excellent! (2,266 reviews)
Great! Go annually. Highly recommend

Reviewed on Feb 25, 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $136 total per night from Mar 29 to Mar 30
$136 total
Mar 29 - Mar 30
Total with taxes and fees
9/10 Wonderful! (864 reviews)
Overcharged and lied to said security deposit was released back but never was

Reviewed on Feb 26, 2026

Berkshire Mountain Lodge
See all 1,352 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 $393 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.