Stockbridge Vacations from $425
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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.
Berkshire Mountain Lodge
$425
per person
Oct 28 - Nov 2
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
9/10 Wonderful! (1,041 reviews)
A real gem. Wonderfully situated. Spacious rooms. Friendly service. I forgot a camera battery charger in the room and the hotel staff kept it for my son to pick up. So very efficient and honest staff. We will definitely consider staying here again.
Reviewed on Aug 15, 2026
Prospect Berkshires
$1,393
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9.8/10 Exceptional! (40 reviews)
Once I got the cabin I expected it was an amazing stay.
Right on the water as shown on the website.
I look forward to my next stay.
Reviewed on Aug 1, 2026
The Whitlock
$654
per person
Oct 22 - Oct 26
found 10 hours ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
8.4/10 Very Good! (343 reviews)
The location is perfect, right on the center of Lenox downtown. Parking at the back of the hotel, though you might not be able to find a parking space if come back late. The room size is ok. But without refrigerator or provide ice station at floor level-not convenient for summer. The floor carpet is old and dirty. The hotel added another antique styled area rug covering the half of the bed area. It looks better but the area rug are not attached to the ground carpet. Easy to get tripped. No room service except replacing towel per request daily. You need to take care your own garbage during your stay. The hotel does have a bar. However, do not expect real bar or meal service. Overall it is a historical old house with great location without too much of the services.
Reviewed on Aug 15, 2026
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View all tripsStay near popular Stockbridge attractions
Norman Rockwell Museum
9.4/10 (347 reviews)
This gallery houses the world's largest collection of Norman Rockwell's iconic American illustrations. Explore his relocated studio on the scenic Berkshire estate for insight into his creative process.
National Shrine of the Divine Mercy
9.0/10 (83 reviews)
This serene sanctuary in the Berkshire Mountains is a center for Divine Mercy devotion inspired by Saint Faustina. Visitors can join the daily 3:00 PM Chaplet or walk contemplative trails.
Naumkeag Museum
9.4/10 (10 reviews)
This Gilded Age estate features a 44-room "cottage" with original Choate family furnishings. Explore the iconic Blue Steps and designed gardens while enjoying panoramic Berkshire Mountain views.
Berkshire Botanical Garden
9.4/10 (14 reviews)
Explore 15 acres of meticulously designed "garden rooms" showcasing over 3,000 plant species native to the Berkshires. The garden's seasonal exhibitions offer an educational journey through horticulture and conservation.
Stockbridge Bowl
This 372-acre Berkshire lake offers serene boating, fishing, and swimming against a backdrop of rolling hills. In winter, Stockbridge Bowl transforms into a magical venue for ice-skating and ice-fishing.
Berkshire Theatre Festival
8.8/10 (3 reviews)
The historic Berkshire Theatre Festival presents classic and contemporary plays in intimate venues. Attend a summer evening performance for an immersive cultural experience in picturesque Stockbridge.
Schantz Galleries
7.2/10 (5 reviews)
This renowned gallery showcased museum-quality glass sculptures from masters like Chihuly and Tagliapietra. Though permanently closed since 2023, its legacy lives on in the contemporary glass art movement.
Mission House
9.6/10 (5 reviews)
This 1739 Georgian home reveals early missionary life and Mohican cultural history. Tour period rooms with exquisite 18th-century American furniture while exploring historically accurate colonial gardens.
Stockbridge Hotel Deals
The Red Lion Inn
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
$209 nightly
$234 total
Sep 9 - Sep 10
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
$358 nightly
$399 total
Aug 31 - Sep 1
Total with taxes and fees
9.2/10 Wonderful! (114 reviews)
"Very lovely beautiful Room and property The outside pool was not available"
Reviewed on Jul 30, 2026
The Inn at Stockbridge
30 East Street Stockbridge MA
$396 nightly
$442 total
Sep 13 - Sep 14
Total with taxes and fees
9.8/10 Exceptional! (101 reviews)
"Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another ..."
Reviewed on Aug 3, 2026
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 $425 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?
- Pick your travel dates: What you want to do in Stockbridge and your preferred season will help you decide when to travel.
- 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.
- 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.
- 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.
- Bundle your airfare and accommodations: After you've settled on your trip dates and duration, book the right Stockbridge vacation package for you.
- 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.
Explore a world of travel with Expedia
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- Where to stay in Stockbridge
- Visit Lee
- Naumkeag Museum
- Visit Great Barrington
- Berkshire Theatre Festival
- Lenox Vacations
- Visit South Lee
- Ski Butternut
- Visit Lenox
- Great Barrington Vacations
- Berkshire Scenic Railway Museum
- Tyringham Cobble
- Kennedy Park
- Ventfort Hall Mansion and Gilded Age Museum
- Visit Stockbridge
- Alford Vacations
- Animagic Museum of Animation
- Bousquet Ski Area
- Berkshire Mountain Country Store
- Ebenezer II Gifts and Antiques
- Berkshire Botanical Garden
- National Shrine of the Divine Mercy
- Goose Pond Reservation
- Lee Premium Outlets
- Wyndhurst Golf & Club
- Frelinghuysen Morris House and Studio
- Tanglewood Music Center
- Chesterwood
- Lenox Library
- Norman Rockwell Museum
- Lee Vacations
- Housatonic River Walk
- Mission House
- South Lee Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
