West Stockbridge Vacations from $421

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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
Price was $484, price is now $421 per person
$421
per person
Dec 15 - Dec 18
found 7 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
7.4/10 Good! (549 reviews)
Nice room, comfortable bed. This is an old grand hotel in tip top shape. We often stay in this type of hotel in NH and VT and found the Equinox to be the best maintained of them all. All the architectural class of its age in virtually new condition. Nice, reasonably priced onsite dining. We didn’t use the large indoor pool but it looked first class. Pleasant staff. We hope to return. Recommend “Ok for breakfast”, a 2nd floor breakfast & lunch restaurant downtown.

Reviewed on Oct 27, 2025

Gedney Farm

Gedney Farm

3.5 out of 5
Price was $819, price is now $584 per person
$584
per person
Dec 27 - Dec 31
found 20 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
9.2/10 Wonderful! (130 reviews)
My wife and I chose Gedney Farms at the last minute to enjoy a quick escape from the city. The staff was friendly and welcoming. The checkin and checkout experience was seamless. The room had a truly rustic charm, and clean and orderly. In the morning we took a nice walk on the grounds. For a quick and relaxing getaway, Gedney Farms is a great choice.

Reviewed on Nov 2, 2025

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,034, price is now $757 per person
$757
per person
Dec 27 - Dec 31
found 10 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (1,005 reviews)
clean room, great breakfast, friendly

Reviewed on Nov 8, 2025

Church Des Artistes Guest House

Church Des Artistes Guest House

3 out of 5
Roundout
Save 100% on your flight
Price was $3,284, price is now $2,688 per person
$2,688
per person
Dec 30 - Jan 2
found 23 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
9.4/10 Exceptional! (18 reviews)
Tru By Hilton Albany Crossgates Mall

Tru By Hilton Albany Crossgates Mall

2.5 out of 5
Price was $528, price is now $459 per person
$459
per person
Dec 30 - Jan 2
found 23 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
8.6/10 Excellent! (1,003 reviews)
Great staff, clean and modern hotel. Beautiful room.

Reviewed on Oct 29, 2025

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Discover the most popular places to visit in West Stockbridge

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

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

Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street, West Stockbridge, MA
$101 nightly
The price is $111 total per night from Nov 12 to Nov 13
$111 total
Nov 12 - Nov 13
Total with taxes and fees
9.6/10 Exceptional! (404 reviews)
Nice place, easy check in

Reviewed on Nov 3, 2025

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
$61 nightly
The price is $67 total per night from Nov 15 to Nov 16
$67 total
Nov 15 - Nov 16
Total with taxes and fees
6.6/10 (1,000 reviews)
Easy to park and check in. Walk up window for motel guest check in. The woman was friendly and got us an extra pillow and came to our room to make sure we had heat. The room was out dated, bathroom clean. I felt like I was sleeping in my grandmother's basement. Has a comfortable bed. A little more ...

Reviewed on Oct 13, 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
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $125 total per night from Nov 12 to Nov 13
$125 total
Nov 12 - Nov 13
Total with taxes and fees
8.6/10 Excellent! (2,127 reviews)
We came here because it was off season, great price, and it had an indoor pool.

Reviewed on Nov 9, 2025

Vacation Village in the Berkshires
See all 1,535 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 $421 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.