Best Resorts in West Stockbridge

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Jun 27 - Jun 29
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Resorts in West Stockbridge

All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Lobby

All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.

2.0 star property
9.8 out of 10, Exceptional, (38)
"This is the second time I've been to Jimminy Peak and this stay was better than the last. The room was clean and comfortable and the ammenities were impeccable "
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Bentley Brook the perfect home base for exploring nearby Berkshire County
Exterior

Bentley Brook the perfect home base for exploring nearby Berkshire County

Bentley Brook the perfect home base for exploring nearby Berkshire County
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Lobby

Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out

Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Interior

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

8.6 out of 10, Excellent, (10)
"Great place to stay very clean and comfortable."
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Property grounds

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!

10.0 out of 10, Exceptional, (1)
"We loved everything about this place! It was quiet, centrally located, and everyone was friendly and helpful. We will stay here again for sure!"
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Bentley Brook the perfect home base for exploring nearby Berkshire County
Exterior

Bentley Brook the perfect home base for exploring nearby Berkshire County

10.0 out of 10, Exceptional, (1)
Bentley Brook the perfect home base for exploring nearby Berkshire County
Lg 1 Bd - Vacation Village in the Berkshires
Lobby

Lg 1 Bd - Vacation Village in the Berkshires

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great spot"
Lg 1 Bd - Vacation Village in the Berkshires
COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE
Outdoor pool, a heated pool

COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE

9.6 out of 10, Exceptional, (17)
"Perfect for a weekend of skiing with the family."
COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE
Bentley Brook 1-bedroom Mountainside ski resort in charming Hancock sleeps 8
Pool

Bentley Brook 1-bedroom Mountainside ski resort in charming Hancock sleeps 8

10.0 out of 10, Exceptional, (1)
"the property was great we had a good time Liana was great answered all of my questions got back to me within a few min and also foud a place for a friend when they couldnt also gaveus a free up grade"
Bentley Brook 1-bedroom Mountainside ski resort in charming Hancock sleeps 8
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Dining

Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

10.0 out of 10, Exceptional, (6)
"Great location, clean and perfect for a family! "
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Property grounds

Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay and it was nice to be so close to the slopes."
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Vacation Village In The Berkshires 5 Star Resort - Suite B
Indoor pool, outdoor pool

Vacation Village In The Berkshires 5 Star Resort - Suite B

Vacation Village In The Berkshires 5 Star Resort - Suite B
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Dining

Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss

10.0 out of 10, Exceptional, (1)
"Walked out of the building, straight into my kids skiing lessons, very convenient."
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
Lobby

Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort

10.0 out of 10, Exceptional, (1)
"We spent a lovely weekend at the Bentley Brook with our kids. The condo is about 200 feet from the nearest lift. The condo is comfortable and spacious. Don't hesitate.."
Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
Exterior

Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl

10.0 out of 10, Exceptional, (1)
"Large property with ski-in/ski-out proximity to Jiminy Peak. Units are standard but large, clean, and with helpful amenities for a family vacation (kitchenette in unit, plus nice pool for kids' apres-ski, kids' movies, etc.) We'll be back."
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
Jiminy Premier Ski-In/Ski-Out Resort Bentley B
Dining

Jiminy Premier Ski-In/Ski-Out Resort Bentley B

10.0 out of 10, Exceptional, (2)
"Great place to get my 6 year old on the mountain. What a great time !"
Jiminy Premier Ski-In/Ski-Out Resort Bentley B
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Dining

Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base

10.0 out of 10, Exceptional, (3)
"This property is great for skiing, especially with kids. There is a nice pool and little movie theater thats prefect for after a day on the slopes."
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Dining

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Dining

Hot SKI-in SKI-out Rentals Bentley Brook Resort!

10.0 out of 10, Exceptional, (1)
"Great property! Great location. Smooth check-in."
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Bentley Brook at Jiminy Peak ^ Studio
Exterior

Bentley Brook at Jiminy Peak ^ Studio

Bentley Brook at Jiminy Peak ^ Studio
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.
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Frequently asked questions

What is West Stockbridge like for a resort vacation?
Longing for a relaxing escape? You deserve the comforts of a resort, where you can find everything you want for your vacation from convenient dining options to activities and entertainment. Browse the resorts in the area and discover the best one for you, whether you envision yourself kicking back in a suite with stunning views or hitting the golf course for an afternoon game.
What's the best resort in West Stockbridge?
Our highest-rated resort near West Stockbridge: Holiday Inn Club Vacations Oak ‘n Spruce Resort - Ski resort. 6.4 mi (10.3 km) from West Stockbridge. Access to a sauna, a fitness center, and a terrace.
What can I do in West Stockbridge?
Travelers enjoy exploring the gardens, and also have good things to say about the dining options here. If you brought the kids, you can head to Charles H. Baldwin & Sons or Hotchkiss Mobile Studio for some family fun. For more to see in the area, you can spend time at Stockbridge Bowl or Ebenezer II Gifts and Antiques.
What's the weather like in West Stockbridge?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in West Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around West Stockbridge?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 7.4 mi (11.9 km) away from the city center. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 17.8 mi (28.7 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.