West Stockbridge Vacations from $388

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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.

The Latest West 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
Price was $485, price is now $388 per person
$388
per person
Oct 15 - Oct 18
found 4 hours ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
8.6/10 Excellent! (1,974 reviews)
Very enjoyable stay in a beautiful location! Clean, comfy, and nicely decorated condo! The staff is so helpful, and absolutely amazing. Couldn’t have had a better place to stay!

Reviewed on Sep 3, 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $591, price is now $431 per person
$431
per person
Nov 5 - Nov 8
found 4 hours ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9/10 Wonderful! (129 reviews)
Rooting for them to make a go of this recently renovated hotel, but the experience was not what one would expect from a 4-star hotel. We had a corner room on a busy street and there was a lot of street noise that could be improved with double-paned windows. The room needed dusting, there was no bath gel in the shower, the walls are thin so could hear our 'neighbors', the kitchen floor needed a sweep, not terrible, but not without crumbs, and worst of all was the refrigerator which was very dirty. There was a slight smell of cooked food as though someone had been eating in there recently.

Reviewed on Sep 3, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was $1,408, price is now $1,032 per person
$1,032
per person
Oct 12 - Oct 16
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
7.4/10 Good! (518 reviews)
Nothing additional to add

Reviewed on Aug 28, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $1,081, price is now $809 per person
$809
per person
Nov 22 - Nov 29
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9/10 Wonderful! (1,004 reviews)
Staff were very friendly and helpful; room clean and very comfortable

Reviewed on Sep 4, 2025

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
Price was $1,174, price is now $930 per person
$930
per person
Nov 22 - Nov 29
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8/10 Very Good! (1,157 reviews)
Staff was inefficient and rude.

Reviewed on Aug 31, 2025

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Discover the most popular places to visit in West Stockbridge

Hoffman's Pottery

Enjoy an outing to Hoffman's Pottery during your stay in West Stockbridge. Wander the lakeside in this quaint area.

Hoffman's Pottery

Ebenezer II Gifts and Antiques

Enjoy an outing to Ebenezer II Gifts and Antiques during your stay in West Stockbridge. Wander the lakeside in this quaint area.

Ebenezer II Gifts and Antiques

Hotchkiss Mobile Studio

Enjoy an outing to Hotchkiss Mobile Studio during your stay in West Stockbridge. Wander the lakeside in this quaint area.

Hotchkiss Mobile Studio

West Stockbridge Hotel Deals

Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street, West Stockbridge, MA
$158 nightly
The price is $174 total per night from Sep 8 to Sep 9
$174 total
Sep 8 - Sep 9
Total with taxes and fees
Shaker Mill Inn
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
$70 nightly
The price is $76 total per night from Sep 9 to Sep 10
$76 total
Sep 9 - Sep 10
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
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 Sep 14 to Sep 15
$145 total
Sep 14 - Sep 15
Total with taxes and fees
Vacation Village in the Berkshires
See all 1,519 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 $388 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?
August, September and November are the best times to search for cheap West Stockbridge vacation packages. Choosing to travel in less busy months means you can typically find better prices on flights and accommodations.
How many days is enough for West Stockbridge?
For your West Stockbridge vacation, a few days will be enough to tour all the highlights. Make sure to check out Chesterwood — it's one of the top attractions in this destination. If you want more adventure, think about basing yourself here and setting off on some tours from West Stockbridge.
Is it worth booking a vacation package to West Stockbridge?
West Stockbridge is a good vacation destination with attractions like Berkshire Botanical Garden among the many things to keep you busy. Whether you're traveling with the family or planning a trip with friends, a West Stockbridge vacation promises a good time for everyone.
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.
Does Expedia offer Book Now, Pay Later West Stockbridge vacation packages?
Your West Stockbridge trip should be an escape from your busy life, not a source of money worries. So to allow you a little more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.