West Stockbridge Vacations from $255

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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 $340, price is now $255 per person
$255
per person
May 7 - May 10
found 23 hours ago
Roundtrip flight included
Raleigh (RDU) to Albany (ALB)
8.8/10 Excellent! (2,134 reviews)
Yes it was clean as usual.

Reviewed on Feb 21, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $731, price is now $481 per person
$481
per person
May 7 - May 10
found 23 hours ago
Roundtrip flight included
Raleigh (RDU) to Albany (ALB)
9/10 Wonderful! (1,002 reviews)
The rooms were beautiful and very comfortable. The cleanliness of the rooms was impeccable. Your complimentary breakfast was outstanding with service by the most pleasant staff. Lindsey and the cooks did an awesome job. Would recommend staying here. We surely will be returning. Thank you.

Reviewed on Feb 11, 2026

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,056, price is now $727 per person
$727
per person
May 7 - May 10
found 23 hours ago
Roundtrip flight included
Raleigh (RDU) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
The cabins are brand new, the property is gorgeous, restaurant features local and quality product and the staff is very responsive via text message. The lakeside sauna is private and easy to reserve. Great place!

Reviewed on Feb 20, 2026

Hilton Garden Inn Saratoga Springs

Hilton Garden Inn Saratoga Springs

3 out of 5
Save 100% on your flight
Price was $1,736, price is now $1,281 per person
$1,281
per person
May 13 - May 20
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
8/10 Very Good! (1,003 reviews)
The sink aerator is too powerful and it splashes water on your belly (or pants). You can't really adjust it. I get it that they are trying to save water, but they need to find a better model (or clean the one installed). There is no towel rack in easy reach of the shower. One of the dresser table lamps did not work.

Reviewed on Feb 16, 2026

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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

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

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

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
$59 nightly
The price is $64 total per night from Feb 22 to Feb 23
$64 total
Feb 22 - Feb 23
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street West Stockbridge MA
$96 nightly
The price is $106 total per night from Mar 4 to Mar 5
$106 total
Mar 4 - Mar 5
Total with taxes and fees
9.6/10 Exceptional! (446 reviews)
Spacious, clean, nice breakfast

Reviewed on Feb 15, 2026

Shaker Mill Inn
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge MA
10/10 Exceptional! (139 reviews)
We always love visiting this house! It is comfortable, clean, and very welcoming. Highly recommend!

Reviewed on Jan 25, 2026

Get rates
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
See all 1,510 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.

Find the Best West Stockbridge Vacation Packages

West Stockbridge Essential Information

Language
English
Currency
U.S dollars
Population
1,450
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 West Stockbridge vacation package cost?
You'll find cheap prices from $255 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.