Deals on vacations and trips to West Stockbridge

Save when you book West Stockbridge package deals

Choose two or more items and save on your trip:

West Stockbridge flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $1,006, price is now $819 per person
$819
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Albany (ALB)
This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and conveniences like a terrace and laundry facilities.
South Shire

South Shire

4 out of 5
Price was $1,512, price is now $1,160 per person
$1,160
per person
Dec 27 - Jan 2
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, express check-in, and express check-out are also on offer.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,713, price is now $1,319 per person
$1,319
per person
Dec 27 - Jan 2
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,050, price is now $841 per person
$841
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 Manchester View

The Manchester View

2.5 out of 5
Price was $1,511, price is now $1,223 per person
$1,223
per person
Dec 27 - Jan 2
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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
$138 nightly
The price is $151 total per night
$151 total
Nov 3 - Nov 4
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
$69 nightly
The price is $76 total per night
$76 total
Oct 6 - Oct 7
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
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.
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
$110 nightly
The price is $123 total per night
$123 total
Nov 1 - Nov 2
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.
Pool
Parking included
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$115 nightly
The price is $128 total per night
$128 total
Nov 3 - Nov 4
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.
Pool
Hot Tub
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
549 Washington Street Hudson NY
Free Cancellation
Reserve now, pay when you stay
$269 nightly
The price is $304 total per night
$304 total
Nov 1 - Nov 2
Total with taxes and fees
This smoke-free hotel features 3 indoor pools, a restaurant, and a bar/lounge. Enjoy the steam room and perks like free valet parking and free WiFi. Free self parking, a coffee shop, and a garden are also offered.
Pool
Spa
Don't see what you're looking for?
See all available properties in West Stockbridge
View all properties
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

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.
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 $819. 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.