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.
Valley Craft Ales

Valley Craft Ales

2 out of 5
Price was CA $925, price is now CA $870 per person
CA $870
per person
Oct 3 - Oct 5
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (143 reviews)
This is a unique stay. I really enjoyed it and would go back. Pictures are accurate. Bare bones, but great price. LOVED the town and area. Comfy bed. Small, but super clean hot water shower. Live music on the weekend - enjoy it!! - done fairly early. No big deal.

Reviewed on Aug. 10, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was CA $2,835, price is now CA $2,315 per person
CA $2,315
per person
Oct 3 - Oct 5
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.4/10 Good! (512 reviews)
When we arrived the front desk had 2 people working with numerous check ins as there was a convention checking in as well as other guests. They were understaffed in many departments. The elevator rug needed replacement as it was dirty and worn. The side entrances were full of large spider webs and debris all the time it appeared no one every cleaned them. It was the disabled entrance. Our bathroom had a serious outdated issue. The hand rails in the tub were rusty and full of soap scum. The outside was in need of a refresh as well most of the iconic green shutters were broken/falling off. It just felt off from the beautiful iconic Equinox Inn of old when the owners took extreme pride in the quality of their quests experiences and comforts.

Reviewed on Aug. 21, 2025

Toll Road Inn

Toll Road Inn

2 out of 5
Price was CA $1,196, price is now CA $1,173 per person
CA $1,173
per person
Oct 3 - Oct 5
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (464 reviews)
Nice, clean small hotel. Very friendly and helpful staff. I would stay there again.

Reviewed on Aug. 20, 2025

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
Price was CA $1,771, price is now CA $1,746 per person
CA $1,746
per person
Oct 3 - Oct 5
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (791 reviews)
Very nice property with friendly staff; excellent food at the restaurant; was only there for 16 hours but definitely want to go back to stay longer.

Reviewed on Aug. 20, 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 $96 per night from Sep 2 to Sep 3
CA $96
CA $105 total
Sep 2 - Sep 3
includes taxes & fees
6.8/10 (995 reviews)
Kathleen from Coventry
"We always enjoy our stay here because of its location to our venue, eating options and the customer friendly owners. It is a bit dated in its interior design, but a clean room wih a clean bed and working shower is our goal. They deliver."

Reviewed on Aug. 18, 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 $228 per night from Aug 27 to Aug 28
CA $228
CA $251 total
Aug 27 - Aug 28
includes taxes & fees
9.6/10 Exceptional! (393 reviews)
Charming stay in the Berkshires
"Only regret is that we did not stay longer! The inn was lovely, and the surrounding gardens were beautiful. With little ground light, we were surrounded by the universe in a way the city doesn’t allow"

Reviewed on Aug. 21, 2025

Shaker Mill 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
The price is CA $147 per night from Sep 11 to Sep 12
CA $147
CA $180 total
Sep 11 - Sep 12
includes taxes & fees
8.6/10 Excellent! (1,961 reviews)
"The property was nice and had activities like a volley ball net and basketball court however no balls were provided. All together the property was very nice but had potential to be nicer. Also daytime front desk staff were not very helpful and actually cranky sounding. Not so pleasant to deal ..."

Reviewed on Aug. 20, 2025

Vacation Village in the Berkshires
See all 1,530 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?
Offering great value package deals from CA $870 on Expedia, you'll be surprised at how little a vacation to West Stockbridge costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to West Stockbridge?
You're likely to find lower rates and greater availability in January, March and December. Browse our cheap West Stockbridge vacation packages and you could land some great off-season deals.
How many days is enough for West Stockbridge?
You can easily explore all the leading sights in West Stockbridge in a few days, including the popular The Mount. If you're after an extended West Stockbridge vacation, look at which kind of day trips and activities are available in the area.
Is it worth booking a vacation package to West Stockbridge?
It's no wonder a West Stockbridge vacation is on the to-do list of many travellers. Major attractions like Berkshire Botanical Garden are just the beginning of what you can explore here.
How to find the best West Stockbridge package deals?
Bagging a cheap West Stockbridge package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply some filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most affordable West Stockbridge package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a West Stockbridge vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still have the flexibility to create a personalized West Stockbridge vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to West Stockbridge?
Enjoy incredible bargains by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu West Stockbridge escape.
How to plan a trip to West Stockbridge?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit West Stockbridge.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and food to activities and airfares. Your hotel will likely be the biggest expense during your trip to West Stockbridge.
  3. Work out your trip length: Think about how much time you'd like to spend exploring West Stockbridge. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, book the ideal West Stockbridge vacation package for you.

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