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.
Valley Craft Ales

Valley Craft Ales

2 out of 5
Price was $775, price is now $642 per person
$642
per person
Sep 17 - Sep 24
found 18 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
This lodge doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and a communal living room are also provided.
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
Save 100% on your flight
Price was $981, price is now $767 per person
$767
per person
Sep 17 - Sep 24
found 18 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
This hotel features a gym and an outdoor tennis court. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Save 100% on your flight
Price was $1,429, price is now $1,119 per person
$1,119
per person
Sep 17 - Sep 24
found 18 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.
The White House Inn

The White House Inn

3.5 out of 5
Save 100% on your flight
Price was $1,264, price is now $1,020 per person
$1,020
per person
Sep 17 - Sep 24
found 18 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace and a garden are also provided.
The Manchester View

The Manchester View

2.5 out of 5
Save 100% on your flight
Price was $1,359, price is now $1,125 per person
$1,125
per person
Sep 17 - Sep 24
found 18 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

Top West Stockbridge hotels deals

Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street West Stockbridge MA
$163 nightly
The price is $179 total per night
$179 total
Jul 7 - Jul 8
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.
Parking included
Free WiFi
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
$74 nightly
The price is $81 total per night
$81 total
Jul 7 - Jul 8
Total with taxes and fees
Free WiFi in public areas is available at this motel. Take advantage of the free self parking.
Parking included
Free WiFi
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
$143 nightly
The price is $159 total per night
$159 total
Jul 7 - Jul 8
Total with taxes and fees
This condo 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.
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
$127 nightly
The price is $142 total per night
$142 total
Jul 7 - Jul 8
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.
Pool
Hot Tub
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$155 nightly
The price is $173 total per night
$173 total
Aug 5 - Aug 6
Total with taxes and fees
This lodge 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.
Pool
Hot Tub
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$211 nightly
The price is $236 total per night
$236 total
Jul 7 - Jul 8
Total with taxes and fees
This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Spa
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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 $642. 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.