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Browse Select Cheshire Resorts

All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Cozy seating area with a fireplace, bench, and sofa, perfect for relaxing.

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

2.0 star property
10.0 out of 10, Exceptional, (41)
"The room was larger than expected and VERY clean. It had everything I needed for a pleasant and relaxing stay while attending the Berkshire Yoga Festival at Jiminy Peak. "
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Bentley Brook the perfect home base for exploring nearby Berkshire County
Set amidst lush greenery, this hotel features a traditional facade with evenly spaced windows and balconies.

Bentley Brook the perfect home base for exploring nearby Berkshire County

10.0 out of 10, Exceptional, (1)
"We just spent a couple nights here but enjoyed our time here. There was plenty of room for 4 people and it was a close walk to the base of Jiminy Peak for the adventure park. Staff was helpful and friendly as well. "
Bentley Brook the perfect home base for exploring nearby Berkshire County
Bentley Brook the perfect home base for exploring nearby Berkshire County
Situated in a lush valley, this hotel offers a traditional architectural style with a symmetrical facade and balconies.

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
COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE
Enjoy a refreshing swim in the pool surrounded by a wooden deck and a white fence.

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
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Enjoy meals at the kitchen's wooden dining table with benches.

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
Lg 1 Bd - Vacation Village in the Berkshires
Relax in the spacious lobby with a comfortable seating area, ornate coffee table, and stunning mountain views.

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
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Relax in a serene outdoor setting surrounded by lush trees and shrubs.

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!
Vacation Village In The Berkshires 5 Star Resort - Suite B
Relax by the pool surrounded by expansive views of the surrounding landscape.

Vacation Village In The Berkshires 5 Star Resort - Suite B

Vacation Village In The Berkshires 5 Star Resort - Suite B
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Cozy living area with a stone fireplace, wooden benches, and a unique chandelier.

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: Ultimate Ski-In Ski-Out -Crazy
Cozy living area with a stone fireplace, wooden bench, and dining table.

Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

9.6 out of 10, Exceptional, (4)
"Very easy access to the slope and perfect for family with kids"
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Cozy gathering space with a stone fireplace, wooden bench, and dining area.

Pres Week- Bentley Brook Resort - Your Peak Winter Escape

9.6 out of 10, Exceptional, (4)
"Bentley Brook is the ideal location for a young family on a ski trip!"
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Cozy gathering space with a stone fireplace, modern TV, and wooden seating area.

Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury

10.0 out of 10, Exceptional, (2)
"This condo was perfect for our family. We had lots of space and we were right on the base of Jiminy peak. I would definitely stay again."
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Enjoy the serene forest views from this balcony with comfortable wicker seating and a small table.

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
Jiminy Premier Ski-In/Ski-Out Resort Bentley B
Cozy living area with a stone fireplace, wooden benches, and a modern TV.

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
Cozy gathering space with a stone fireplace, modern TV, and bar area.

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
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
Stroll through the serene outdoor space, featuring a charming gazebo and a beautifully manicured lawn.

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
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Cozy gathering space with a large stone fireplace, modern TV, and comfortable seating area.

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

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Cozy gathering space with a stone fireplace, rustic seating, and a bar area.

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
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Cozy living area with a stone fireplace, wooden bench, and plush seating.

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!
Holiday Inn Club Vacations Oak 'n Spruce Resort
Room

Holiday Inn Club Vacations Oak 'n Spruce Resort

2.0 star property
Holiday Inn Club Vacations Oak 'n Spruce Resort
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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Top Cheshire Hotel Reviews

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"My stay was perfect. I can't wait to stay there again. "
RICHARD 2-night trip
Posted 1 day ago
Howard Johnson by Wyndham Lenox