West Stockbridge Vacation Packages

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Your West Stockbridge Vacation

Enjoy amazing adventures when you lock in a West Stockbridge vacation package. Whether you're a history buff, foodie or just a traveler who loves to experience new places, there's something for everyone in this lively city. Every trip to West Stockbridge needs a well-thought-out itinerary. Fill yours with big-name attractions like Tanglewood Music Center, National Shrine of the Divine Mercy and Norman Rockwell Museum. Whoever you're taking a break with and whether your budget is big or small, your ultimate West Stockbridge vacation is only clicks away with Expedia.

Top West Stockbridge Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

3 out of 5
per person
Apr. 8 - Apr. 15
found 21 hours ago
Roundtrip flight included
Québec (YQB) to Albany (ALB)
9.2/10 Wonderful! (498 reviews)
Have been coming to Bentley for years- love the ski on/ski off for JiminyPeak. The staff is very nice, very welcoming- a definite keeper!

Reviewed on Feb. 1, 2025

Brook Bound Inn

Brook Bound Inn

2 out of 5
per person
Apr. 8 - Apr. 15
found 21 hours ago
Roundtrip flight included
Québec (YQB) to Albany (ALB)
9.4/10 Exceptional! (10 reviews)
Great property. Amazing views!

Reviewed on Dec. 2, 2024

Eddington House Inn

Eddington House Inn

3 out of 5
North Bennington Historic District
per person
Apr. 8 - Apr. 15
found 21 hours ago
Roundtrip flight included
Québec (YQB) to Albany (ALB)
9.2/10 Wonderful! (79 reviews)
It was one of the best Breakfast's I have ever had.

Reviewed on Dec. 4, 2024

Home Near Hiking Biking w Hottub 6 Bedrooms

Home Near Hiking Biking w Hottub 6 Bedrooms

2 out of 5
Save 100% on your flight
per person
Apr. 8 - Apr. 15
found 21 hours ago
Roundtrip flight included
Québec (YQB) to Albany (ALB)
No reviews
South Shire

South Shire

4 out of 5
per person
Apr. 8 - Apr. 15
found 21 hours ago
Roundtrip flight included
Québec (YQB) to Albany (ALB)
9.2/10 Wonderful! (80 reviews)
The Southshire is a beautiful vintage home with original details, great charm, working original fireplace in the large cozy wood paneled parlor. There are games, large comfy sofas, and bookcases full of every genre of books for reading. The dining room is lovely and quaint. My room in the carriage house was very large and furnished with antiques and a working fireplace. Joe, the owner, was extremely nice and very accommodating. He even spent a half hour with me digging my car out of the snow and ice and literally pushing my car out of a snow pile! I can highly recommend a stay at this charming Inn if you are looking for true New England authenticity. Thank you Joe for making this a special place.

Reviewed on Feb. 17, 2025

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West Stockbridge Hotel Deals

Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
2 out of 5
42 Stockbridge Rd, West Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Mar. 8 to Mar. 9
CA $87
CA $96 total
includes taxes & fees
Mar 8 - Mar 9
6.8/10 (963 reviews)
Clean room
"The room and bathroom were very clean."

Reviewed on Jan. 3, 2025

Pleasant Valley Motel West Stockbridge
Shaker Mill Inn
Shaker Mill Inn
2.5 out of 5
2 Oak Street, West Stockbridge, MA
The price is CA $208 per night from Mar. 9 to Mar. 10
CA $208
CA $228 total
includes taxes & fees
Mar 9 - Mar 10
9.6/10 Exceptional! (379 reviews)
"Beautiful room, very clean. breakfast was not what i was expecting, walk way from parking lot covered with ice and snow, very dangerous to walk, needs to be cleaned or at least put some salt on the ground. other then that everything was excellent. will stay again"

Reviewed on Feb. 23, 2025

Shaker Mill Inn
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Stockbridge
9.8/10 Exceptional! (113 reviews)
College Roomates Reunion
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite."

Reviewed on Dec. 8, 2024

Get rates
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
See all 1,473 properties in West 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 West Stockbridge vacation package cost?
You’ll find cheap prices from CA $1,135 on Expedia for your West Stockbridge break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to West Stockbridge costs.
What are the cheapest months to go to West Stockbridge?
January, March and December are the best times to search for cheap West Stockbridge vacation packages. Traveling in quieter periods means you can typically find reduced prices on accommodations and flights.
How many days is enough for West Stockbridge?
For a West Stockbridge vacation, a few days will be enough to tour the best spots. Make sure to visit Ebenezer II Gifts and Antiques — it’s one of the most popular attractions in this destination. If you’re looking for more activities, think about basing yourself here and going on some day trips from West Stockbridge.
Is it worth booking a vacation package to West Stockbridge?
West Stockbridge offers everything you need for a wonderful escape. Get your West Stockbridge vacation off to a flying start by checking out major attractions like Berkshire Botanical Garden.
How to find the best West Stockbridge package deals?
Landing a cheap West Stockbridge package deal is easy with Expedia. Once you’ve entered your destination and trip dates under our “Packages” tab, set your budget range, add a couple of filters and see what’s available. You can fine-tune your search by “Amenities,” “Property type,” “Traveler experience” and more. Order the results by “Price: low to high” to discover the most affordable West Stockbridge package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a West Stockbridge vacation as a package?
You can enjoy significant savings on your West Stockbridge break by booking a personalized vacation package. Check the “Package” heading, then select your destination and travel dates to browse the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to West Stockbridge?
If you have your West Stockbridge travel dates finalized, book as soon as you can to grab some awesome deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are ideal for quick escapes.
How to plan a trip to West Stockbridge?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to West Stockbridge.
  2. Plan your budget wisely: As well as the cost of your stay, you’ll need to factor in other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to West Stockbridge.
  3. Determine how many days away: Start by making a list of all the activities and sights you’d like to experience in West Stockbridge. Then, estimate how long you’ll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized West Stockbridge vacation package.

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