West Stockbridge Holidays

  • Plan, book, travel with confidence
    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in West Stockbridge

Shaker Mill Inn
Shaker Mill Inn
2.5 out of 5
2 Oak Street, West Stockbridge, MA
The price is S$214 per night from 25 Nov to 26 Nov
S$214
includes taxes & fees
25 Nov - 26 Nov
9.6/10 Exceptional! (371 reviews)
"This place is so comfortable and roomy. Perfect place for a quiet getaway."

Reviewed on 20 Oct,2024

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
The price is S$87 per night from 28 Nov to 29 Nov
S$87
includes taxes & fees
28 Nov - 29 Nov
6.8/10 (955 reviews)
"Well located near attractions"

Reviewed on 29 Oct,2024

Pleasant Valley Motel West Stockbridge
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is S$278 per night from 1 Dec to 2 Dec
S$278
includes taxes & fees
1 Dec - 2 Dec
8.8/10 Excellent! (1,001 reviews)
"Didn’t like that there are no trays in shower to hold any soaps or bottles while washing… nothing!!! Tub too high for elderly with slightest arthritis. No curtain on shower bathroom window. Took quite a while to get hot water to wash hands in sink. However, the inn is filled with amazing collectibles. ..."

Reviewed on 20 Nov,2024

The Red Lion Inn
See all 1,436 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.

Frequently asked questions

How much does a West Stockbridge holiday package cost?
Live it up in West Stockbridge from just . Choose from a wonderful selection of rental cars, hotels and flights to suit every budget. You can score even better deals when you add a few tours or activities to your holiday package.
How do I get a cheap travel package to West Stockbridge?
Combine your flight and hotel bookings, throw in extras such as a rental car or activities, and save with a West Stockbridge holiday package. You won’t just enjoy exciting discounts on your trip — you’ll have a world of choice at your fingertips too. When you book with Expedia, you can select from more than 550 airlines and 1,000,000 hotels around the world. Your next grand adventure starts right here, right now!
Where should I stay in West Stockbridge?
With loads to explore in West Stockbridge, we suggest you secure a room in a hotel near its attractions. Berkshire Botanical Garden, Chesterwood and Ebenezer II Gifts and Antiques are some good ones to add to your to-do list.
What are the top hotels in West Stockbridge?
Get your holiday off to a great start by reserving a room at Beautiful Modern Farmhouse - Heart Of The Berkshires. It’s one of most popular hotels in West Stockbridge. Another comfortable option is Berkshires Forest Retreat With Hot Tub.
How far in advance should I book my West Stockbridge holiday?
While prices do change, we generally suggest booking your holiday as early as possible. Many international airfares can be compared on Expedia up to a year in advance. If circumstances have left you booking last minute, you might still be in luck. Cheap tickets to West Stockbridge sometimes appear only weeks before departure.
What does an Expedia West Stockbridge travel package include?
Flights, rental cars and hotels — we’ve got them all. With Expedia, you can create your West Stockbridge package just the way you want. All you have to do is decide just what you need. Once you’ve made your booking, you can add extras like activities and tours. The more you bundle, the greater the savings!
What should I know before booking a West Stockbridge travel package?
You can save big by combining your hotels, airfares and rental cars. Once you’ve created your package, you can add on things like activities or sightseeing tours. Your next awesome adventure is only a couple of clicks away.
Can I choose my airline with a West Stockbridge Expedia holiday package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the flexibility to take your pick of available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my West Stockbridge holiday package?
Don’t stress if you’re rethinking your West Stockbridge holiday package — you can cancel or change your booking. And if you’ve booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We totally get that your circumstances can change suddenly, so head to our Customer Service Portal if that happens. When you’re ready to make changes, we’ll be here to help.

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

* 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.