Best Resorts in Hampshire County

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Top Cities in Hampshire County

Resorts in Hampshire County

Publick House Historic Inn and Country Motor Lodge

2.5 star property
8.8 out of 10, Excellent, (1499)
"Loved staying there. "
$99 nightly
The price is $111
Sep 7 - Sep 8
Total with taxes and fees
Publick House Historic Inn and Country Motor Lodge

Sturbridge Host Hotel & Conference Center

3.0 star property
6.4 out of 10, (1004)
"Friendly good location "
$120 nightly
The price is $134
Sep 7 - Sep 8
Total with taxes and fees
Sturbridge Host Hotel & Conference Center

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

2.0 star property
10.0 out of 10, Exceptional, (42)
"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.

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

8.8 out of 10, Excellent, (11)
"Great place to stay very clean and comfortable."
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

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

9.6 out of 10, Exceptional, (17)
"Perfect for a weekend of skiing with the family."
COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE

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

10.0 out of 10, Exceptional, (2)
"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 - 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

Vacation Village In The Berkshires 5 Star Resort - Suite B

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

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

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 - B

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

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

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: 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

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

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!

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
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

Find out more about Hampshire County

Find out more about Hampshire County

Resorts and More in Hampshire County

Expedia can help you find resorts and other lodging options that provide similar services and comforts. If you're having trouble finding a resort in Hampshire County that meets your needs, try using the search page filters to look for 4- and 5-star hotels, or search for properties that offer amenities like pools or all-inclusive options. We make it simple to book great accommodations so you can focus on creating your trip itinerary.


What Can I Do in Hampshire County?


If you're interested in popular sights, Volleyball Hall of Fame, Naismith Memorial Basketball Hall of Fame, and MassMutual Center are top places to visit nearby. Additional attractions in the area include Smith College Botanic Garden and MGM Springfield.


Travelers also like Hampshire County for its:

  • Flowers
  • University life
  • Art
  • Coffee
  • Forests

When Should I Visit Hampshire County?


Here's a summary of the typical weather to help with deciding vacation dates:


  • The hottest months are typically July and August, while January and February are the coldest months
  • January-March: Daytime temperatures average 52° F and nighttime temperatures average 18° F
  • April-June: 81° F is the daytime average and 35° F is the nighttime average
  • July-September: Daytime averages are around 83° F and nighttime averages are around 48° F
  • October-December: The average temperatures are 67° F during the day and 21° F at night
  • Average rainfall is 44.68 inches in a year

How to Get to Hampshire County and Around the Area



Hampshire County Transportation
NameTypeDistance
Westfield, MA (BAF-Barnes Municipal)Airport11.3 mi (18.1 km)
Hartford, CT (BDL-Bradley Intl.)Airport27.2 mi (43.8 km)

Hampshire County Resorts information

Number of reviews
Accommodation
39 Resorts
Lowest Price
$111
Highest Price
$134

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Explore a world of travel with Expedia

Frequently asked questions

Why book your resort in Hampshire County with Expedia?
With Expedia, you'll have no trouble finding your ideal resort in Hampshire County. Vacationing with the kids? Take advantage of our filters to search for properties with perks like a water park. If you have a budget, select how much you want to spend and the preferred star rating of your stay. We'll help you find a suitable place whatever your getaway looks like.
How can I find cheap resorts in Hampshire County?
Expedia is here to help you narrow your search for cheap resorts in Hampshire County. Use our filter tool to select star rating, budget and amenities to tailor your search and find your dream stay in a matter of clicks.