Deals on vacations and trips to West Stockbridge

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West Stockbridge flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $482, price is now $380 per person
$380
per person
Oct 14 - Oct 17
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
This aparthotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,108, price is now $784 per person
$784
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.
The Whitlock

The Whitlock

2 out of 5
Price was $1,041, price is now $745 per person
$745
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, a terrace, and a garden are also on offer.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $514, price is now $395 per person
$395
per person
Oct 14 - Oct 17
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
This aparthotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
Price was $592, price is now $477 per person
$477
per person
Oct 14 - Oct 17
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

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
$69 nightly
The price is $76 total per night
$76 total
Aug 20 - Aug 21
Total with taxes and fees
Free WiFi in public areas is available at this motel. Take advantage of the free self parking.
Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street West Stockbridge MA
$178 nightly
The price is $196 total per night
$196 total
Sep 8 - Sep 9
Total with taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. A library is also provided.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

Stockbridge MA
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
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
$128 nightly
The price is $143 total per night
$143 total
Aug 31 - Sep 1
Total with taxes and fees
This aparthotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$158 nightly
The price is $176 total per night
$176 total
Sep 14 - Sep 15
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$125 nightly
The price is $139 total per night
$139 total
Aug 31 - Sep 1
Total with taxes and fees
This aparthotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
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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

Frequently asked questions

How much are vacation packages to West Stockbridge?
You can find an awesome flight and hotel bundle for as little as $380. 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 110 mi 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 45 mi from downtown and is the starting point for many adventures. Alternatively, Albany Intl. Airport (ALB) is 35 mi away from central West Stockbridge and Hartford, CT (HFD-Hartford - Brainard) is 55 mi 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.