West Stockbridge Vacations from $751

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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.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
Aug 12 - Aug 16
found 22 hours ago
Roundtrip flight included
New York (JFK) to Albany (ALB)
7.4/10 Good! (483 reviews)
I had a wonderful time and did Rhumba for the first time in the pool! Lovely walk to the pond also!

Reviewed on Jun 23, 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 10
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
9.2/10 Wonderful! (34 reviews)
Wonderful property. Exceptional staff. Will be back.

Reviewed on Jun 26, 2025

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 10
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
No reviews
Hampton Inn Schenectady Downtown

Hampton Inn Schenectady Downtown

2.5 out of 5
Seward Place
per person
Aug 6 - Aug 10
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
9/10 Wonderful! (915 reviews)
Clean room. Friendly staff.

Reviewed on Jun 24, 2025

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
per person
Aug 6 - Aug 10
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
8.4/10 Very Good! (662 reviews)
Overall nice clean hotel . Need to update tvs so you can use streaming services. Need to update website about complimentary breakfast and late check out .

Reviewed on Jun 1, 2025

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Discover the most popular places to visit in West Stockbridge

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

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

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
$70 nightly
The price is $76 total per night from Jul 6 to Jul 7
$76 total
Jul 6 - Jul 7
Total includes taxes and fees
6.8/10 (972 reviews)
"Great location for my activities."

Reviewed on Jun 8, 2025

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
$125 nightly
The price is $139 total per night from Jun 29 to Jun 30
$139 total
Jun 29 - Jun 30
Total includes taxes and fees
8.6/10 Excellent! (1,836 reviews)
"The property was perfect for a getaway. 1 bedroom suite or more with balconies. Non heating Fireplace for aesthetics. The suite was a jack and Jill! Shower, but also a jet tub separate from shower. All dishes and cooking utensils that you needed. You can grill onsite or cook in your suite as take ..."

Reviewed on Jun 24, 2025

Vacation Village in the Berkshires
Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $132 total per night from Jul 13 to Jul 14
$132 total
Jul 13 - Jul 14
Total includes taxes and fees
8.2/10 Very Good! (1,003 reviews)
"The gentleman working at the front desk was extremely helpful when were in a pinch and needed assistance late at night! The second-level room was comfortable, clean, and quiet, and the location is amazing, just a short walk to all the restaurants, cafes and shops that downtown Great Barrington has ..."

Reviewed on Jun 26, 2025

Quality Inn
See all 1,520 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 $751 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.