Stockbridge Vacations from $439

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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.
Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $597, price is now $439 per person
$439
per person
Oct 11 - Oct 14
found 21 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (72 reviews)
Very zen, peaceful ambiance. Lovely stay!

Reviewed on Aug 18, 2025

The Wiltwyck

The Wiltwyck

3.5 out of 5
Save 100% on your flight
Price was $763, price is now $555 per person
$555
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.4/10 Exceptional! (153 reviews)
Lakefront Terrace Resort

Lakefront Terrace Resort

3 out of 5
Save 100% on your flight
Price was $709, price is now $525 per person
$525
per person
Oct 11 - Oct 14
found 21 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.2/10 Very Good! (938 reviews)
The view is beautiful! The rooms just need to be cleaned better and the balcony needs a really good cleaning. The property has a lot of potential.

Reviewed on Aug 19, 2025

Hampton Inn Schenectady Downtown

Hampton Inn Schenectady Downtown

2.5 out of 5
Seward Place
Price was $653, price is now $488 per person
$488
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9/10 Wonderful! (944 reviews)
nice to grab a coffee before heading out in the mornin

Reviewed on Aug 14, 2025

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Save 100% on your flight
Price was $744, price is now $557 per person
$557
per person
Oct 11 - Oct 14
found 21 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9.4/10 Exceptional! (484 reviews)
Loved the lodge, beautiful grounds and convenience to downtown Lake George. Only con was that our lodge was near the maintenance shed, which at times was quite loud. This was a slight annoyance. Wouldn't stop me from booking again

Reviewed on Jul 25, 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

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
$227 nightly
The price is $254 total per night from Aug 26 to Aug 27
$254 total
Aug 26 - Aug 27
Total includes taxes and fees
8.8/10 Excellent! (1,007 reviews)
"Very clean, fantastic staff, comfortable bed, robes to use gping to the pool/jacuzzi, plus the large bottles of water in the room."

Reviewed on Aug 14, 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 Aug 21 to Aug 22
$269 total
Aug 21 - Aug 22
Total includes taxes and fees
7/10 Good! (19 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
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
$130 nightly
The price is $145 total per night from Aug 27 to Aug 28
$145 total
Aug 27 - Aug 28
Total includes taxes and fees
8.6/10 Excellent! (1,950 reviews)
Love Vacation Village!
"Love everything about this place. If you want a true home away from home this is the place. The only miss is streaming abilities for at night, but an extra hdmi to type C cable,and we were all set!"

Reviewed on Aug 16, 2025

Vacation Village in the Berkshires
See all 1,369 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.

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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 $439 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.