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West Stockbridge flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
South Shire

South Shire

4 out of 5
Price was CA $1,560, price is now CA $1,350 per person
CA $1,350
per person
Oct 9 - Oct 12
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
Stay at this B&B in Bennington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bennington Arts Guild Gallery and Fiddlehead at Four Corners are located nearby.
Ambler Hotel

Ambler Hotel

2 out of 5
Price was CA $3,972, price is now CA $3,399 per person
CA $3,399
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Albany (ALB)
Stay at this hotel in Saratoga Springs. Enjoy free WiFi, free parking, and Netflix. Popular attractions Saratoga Racetrack and Saratoga Casino are located nearby.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was CA $2,161, price is now CA $1,879 per person
CA $1,879
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Albany (ALB)
Stay at this hotel in Saratoga Springs. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saratoga Casino and Saratoga Racetrack are located nearby.
Wilburton Inn

Wilburton Inn

3.5 out of 5
Price was CA $1,728, price is now CA $1,526 per person
CA $1,526
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Detroit (DTT) to Albany (ALB)
Book a stay at this golf hotel in Manchester. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Museum of Creative Process and Hildene are located nearby.
Hilton Garden Inn Saratoga Springs

Hilton Garden Inn Saratoga Springs

3 out of 5
Price was CA $2,466, price is now CA $2,188 per person
CA $2,188
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Albany (ALB)
Book a stay at this business-friendly hotel in Saratoga Springs. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Saratoga Casino and Saratoga Racetrack are located nearby.

Top West Stockbridge hotels deals

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2 out of 5
42 Stockbridge Rd West Stockbridge MA
Free cancellation
Reserve now, pay when you stay
The price is CA $95 per night
CA $95
CA $105 total
Aug 24 - Aug 25
includes taxes & fees
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Hoffman's Pottery are located nearby.
Parking included
Free WiFi
Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street West Stockbridge MA
The price is CA $234 per night
CA $234
CA $256 total
Sep 8 - Sep 9
includes taxes & fees
Stay at this B&B in West Stockbridge. Enjoy free parking and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer II Gifts and Antiques are located nearby.
Parking included
Free WiFi
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

Stockbridge MA
Get rates
Book a stay at this family-friendly vacation home in West Stockbridge. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Tanglewood Music Center and Stockbridge Bowl are located nearby.
Kitchen
Washer
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free cancellation
Reserve now, pay when you stay
The price is CA $120 per night
CA $120
CA $149 total
Aug 31 - Sep 1
includes taxes & fees
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Pool
Parking included
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
The price is CA $176 per night
CA $176
CA $196 total
Sep 16 - Sep 17
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
The price is CA $130 per night
CA $130
CA $176 total
Aug 31 - Sep 1
includes taxes & fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
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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.

Stay near popular West Stockbridge attractions

Hotchkiss Mobile Studio

9.6/10 (4 reviews)
Enjoy an outing to Hotchkiss Mobile Studio during your stay in West Stockbridge. Wander the lakeside in this quaint area.
See properties

West Stockbridge Vacations

A smooth, trouble-free getaway starts with getting to know a thing or two about your destination. It's time to acquaint yourself with the fundamentals about West Stockbridge!

To help you get your bearings, West Stockbridge is 110 miles (177 kilometers) to the north of the significant city of New York.

Traveling is about meeting people, so why not make friends with some of the 1,000 locals who reside in this area of The Berkshires?

Hotels in West Stockbridge

West Stockbridge been on your travel radar for a long time? Get ready to tick it off! Travelocity features 13 properties for you to check out.

The 1862 Seasons on Main Bed and Breakfast (47 Main Street) or the Stockbridge Country Inn (26 Glendale Road) are perfect for those wanderers looking for quality service and soft, silky sheets. The Briarcliff Motel (506 Stockbridge Road) and the Travelodge by Wyndham Great Barrington Berkshires (400 Stockbridge Rd) are some thrifty options if you'd prefer to spend your cash on experiences.

Places to visit in West Stockbridge

Nothing compares to seeing excellent art when your soul needs lifting. As you marvel at the fabulous works at Norman Rockwell Museum, try to find a deeper meaning. Need some more options? History is the best teacher. Journey back through time for a lesson at Chesterwood. And that's not all. Grab your favorite novel, find a secluded spot and take a moment to bask in the revitalizing garden fragrances at Berkshire Botanical Garden.

Where do you fly into for West Stockbridge?

Prepare for some new adventures in West Stockbridge. Once you've walked out of Bradley International Airport (BDL), the main streets will be 45 miles (72 kilometers) to the northwest.

Frequently asked questions

How much are vacation packages to West Stockbridge?
You can find an awesome flight and hotel bundle for as little as CA $1,350. With one of our Travelocity vacation packages, a getaway in West Stockbridge has never looked more irresistible! Save some time and money and then get a head start on packing those bags.
How long should my West Stockbridge vacation be?
Around 2 nights is the average amount of time visitors vacation in West Stockbridge. But how long is right for you all depends on how many magical memories you want to make. Why not allow a little more time and uncover some hidden gems?
Where can I get the best vacation package deals for West Stockbridge?
With at least 400 air carriers and 1,000,000 properties all over the world, it's hard to beat Travelocity. Scroll through our extensive range and pick up the best West Stockbridge package deal. Isn't it great when trip planning is that easy?
Why should I book my West Stockbridge vacation package with Travelocity?
Travel is all about making fantastic new memories and leaving all your troubles behind — which is why we provide you with a professional team of customer service experts available round-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our terrific range of vacation destinations. So what are you waiting for? There's no time like the present to secure the vacation you've always dreamed of.
Can I save on my West Stockbridge car rental if I bundle it with my hotel or flight?
Bundling your flight, car and hotel into a West Stockbridge vacation package is an easy way to land the best deal. Plus, having your own car rental gives you the freedom to get to all those big sights you'd like to explore. Located 177 kilometers from West Stockbridge, Times Square is one attraction that should be on your agenda. Top up the tank and make a day trip of it.
Which airport is best for West Stockbridge?
Bradley Intl. Airport (BDL) is 72 kilometers from downtown and is the starting point for many adventures. Alternatively, Albany Intl. Airport (ALB) is 56 kilometers away from central West Stockbridge and Hartford, CT (HFD-Hartford - Brainard) is 88 kilometers away from central West Stockbridge.
What is there to do in West Stockbridge?
You'll sense a certain magic in the air as you stroll through the streets of West Stockbridge. Berkshire Botanical Garden and Ebenezer II Gifts and Antiques are just a couple of famous sights that lure visitors to this fantastic city, so put them on your itinerary.
Where should I stay when visiting West Stockbridge?
If you're after somewhere to spend your nights, have a look at the Shaker Mill Inn. It's the top pick for many visitors.

Photos of local treasures

Browse West Stockbridge vacation photos for more inspiration

A mountainous landscape with a lake and dense forests.
A lush green valley with a lake and a house in the distance.
A river under a bridge with snow on the banks and buildings on either side.