Resorts in Hampshire County

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Hampshire County resorts

Outdoor wedding area
Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

2.5 star property
Sturbridge
9.0 out of 10, Wonderful, (1574)
"Great place"
United States
John
The price is SAR 301
SAR 336 total
includes taxes & fees
7 Jan - 8 January 2026
Publick House Historic Inn and Country Motor Lodge
Indoor pool
Sturbridge Host Hotel & Conference Center

Sturbridge Host Hotel & Conference Center

3.0 star property
Sturbridge
6.4 out of 10, (1001)
"Really interesting and cool place"
United States
Hillary
Sturbridge Host Hotel & Conference Center
Outdoor pool, a heated pool
COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.

COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.

Hancock
9.6 out of 10, Exceptional, (18)
"Perfect for a weekend of skiing with the family."
United States
Michael D.
COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.
Interior
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

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

Hancock
9.0 out of 10, Wonderful, (12)
"Great stay! It was perfect for 1. The owner was incredibly friendly and responsive to all of my questions (even the little ones), both before and during my stay. I loved the view from the balcony and the jetted tub. The bed while very low, was surprisingly really comfortable. "
United States
Jennifer F.
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Exterior
Bentley Brook the perfect home base for exploring nearby Berkshire County

Bentley Brook the perfect home base for exploring nearby Berkshire County

Hancock
10.0 out of 10, Exceptional, (2)
"Beautiful location, room was very clean,comfortable beds, wonderful guest service. Activities for kids, pool hot tub arcade. Skiing and snowboarding. Would highly recommend "
United States
Elaine M.
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

Hancock
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

Hancock
9.6 out of 10, Exceptional, (4)
"Nice and comfortable. Desk was still on duty when we arrived quite late for check in. Room was spacious and clean. Will probably stay there again when we are in the area. "
United States
Gabrielle C.
Bentley Brook the perfect home base for exploring nearby Berkshire County
Lobby
1 Bd - Vacation Village in the Berkshires

1 Bd - Vacation Village in the Berkshires

2.0 star property
Hancock
10.0 out of 10, Exceptional, (2)
"We enjoyed staying at this clean, quiet, and comfy property. Close to so many beautiful spots! Only minutes to both New York and Vermont!"
United States
Erin T.
1 Bd - Vacation Village in the Berkshires
Property grounds
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A

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

Hancock
10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay and it was nice to be so close to the slopes."
United States
Carrie C.
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Dining
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

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

Hancock
10.0 out of 10, Exceptional, (6)
"Great location, clean and perfect for a family! "
United States
Allison A.
The price is SAR 2,064
SAR 2,637 total
includes taxes & fees
31 Dec - 1 January 2026
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Indoor pool, outdoor pool
Vacation Village In The Berkshires 5 Star Resort - Suite B

Vacation Village In The Berkshires 5 Star Resort - Suite B

Hancock
Vacation Village In The Berkshires 5 Star Resort - Suite B
Dining
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury

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

hancock
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."
United States
Leanne W.
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Property grounds
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B

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

Hancock
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
Dining
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

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

Hancock
9.6 out of 10, Exceptional, (4)
"Very easy access to the slope and perfect for family with kids"
United States
Jung Y.
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Dining
Jiminy Premier Ski-In/Ski-Out Resort Bentley B

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

Hancock
10.0 out of 10, Exceptional, (2)
"Great place to get my 6 year old on the mountain. What a great time !"
United States
Robert K.
Jiminy Premier Ski-In/Ski-Out Resort Bentley B
Dining
Hot SKI-in SKI-out Rentals Bentley Brook Resort!

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

Hancock
10.0 out of 10, Exceptional, (1)
"Great property! Great location. Smooth check-in."
United States
erica l.
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Dining
Pres Week- Bentley Brook Resort - Your Peak Winter Escape

Pres Week- Bentley Brook Resort - Your Peak Winter Escape

Hancock
9.6 out of 10, Exceptional, (4)
"Bentley Brook is the ideal location for a young family on a ski trip!"
United States
Jordana A.
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Dining
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base

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

Hancock
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."
United States
Erica M.
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Exterior
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl

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

Hancock
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."
United States
Eileen S.
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
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

Hancock
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out 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 Hampshire County Hotel Reviews

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

10/10 Excellent
"Perfect spot for your vacations! Highly recommended!!!"
Mildred 4-night trip
Posted 16 hours ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

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