West Stockbridge Holidays

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Top hotels in West Stockbridge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2 out of 5
42 Stockbridge Rd, West Stockbridge, MA
The price is S$98 per night from 9 Sept to 10 Sept
S$98
9 Sept - 10 Sept
includes taxes & fees
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 S$234 per night from 4 Sept to 5 Sept
S$234
4 Sept - 5 Sept
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 21 Aug, 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 S$169 per night from 14 Sept to 15 Sept
S$169
14 Sept - 15 Sept
includes taxes & fees
8.6/10 Excellent! (1,969 reviews)
"The staff at Vacation Village are simply amazing! Super nice and very helpful. Very clean, lots of amenities, and spacious rooms! Will definitely stay again!"

Reviewed on 24 Aug, 2025

Vacation Village in the Berkshires
See all 1,514 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.

Popular places to visit

Charles H. Baldwin & Sons

Enjoy an outing to Charles H. Baldwin & Sons during your stay in West Stockbridge. Wander the lakeside in this quaint area.

Charles H. Baldwin & Sons

Frequently asked questions

How much does a West Stockbridge holiday package cost?
You'll find cheap prices 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 holiday to West Stockbridge costs.
What are the cheapest months to go to West Stockbridge?
January, March and December are the best times to search for cheap West Stockbridge holiday packages. Travelling in quieter periods means you can typically find reduced prices on accommodation and flights.
How many days is enough for West Stockbridge?
For a West Stockbridge holiday, a few days will be enough to tour the best spots. Make sure to visit Ebenezer II Gifts and Antiques — it's one of the most popular attractions in this destination. If you're looking for more activities, think about basing yourself here and going on some day trips from West Stockbridge.
Is it worth booking a holiday package to West Stockbridge?
West Stockbridge offers everything you need for a wonderful escape. Get your West Stockbridge holiday off to a flying start by checking out major attractions like Berkshire Botanical Garden.
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," "Traveller 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 holiday as a package?
You can enjoy significant savings on your West Stockbridge break by booking a personalised holiday package. Check the "Package" heading, then select your destination and travel dates to browse the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday 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.
How to plan a trip to West Stockbridge?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to West Stockbridge.
  2. Plan your budget wisely: As well as the cost of your stay, you'll need to factor in other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to West Stockbridge.
  3. Determine how many days away: Start by making a list of all the activities and sights you'd like to experience in West Stockbridge. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalised West Stockbridge holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.