Photo by Elizabeth Massa Peroulakis
Search Resorts in Middlefield
Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Resorts in Middlefield
Compare 25 Resorts in Middlefield with updated reviews, rates, and availability.
Ski resort, Wydham Bently Brook in Berkshire mountains, MA
Ski resort, Wydham Bently Brook in Berkshire mountains, MA
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
10.0 out of 10, Exceptional, (2)
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Save an average of 15% on thousands of hotels when you're signed in
Luxury one bedroom and one bathroom unit with full amenities
Luxury one bedroom and one bathroom unit with full amenities
Luxury one bedroom and one bathroom unit with full amenities
Luxury one bedroom and one bathroom unit with full amenities
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
8.4 out of 10, Very Good, (5)
Cozy Cabin on resort property in Cultural Berkshires. Pets are welcome!
Cozy Cabin on resort property in Cultural Berkshires. Pets are welcome!
9.8 out of 10, Exceptional, (13)
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
10.0 out of 10, Exceptional, (1)
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
10.0 out of 10, Exceptional, (2)
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Vacation Village In The Berkshires 5 Star Resort - Suite B
Vacation Village In The Berkshires 5 Star Resort - Suite B
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
10.0 out of 10, Exceptional, (2)
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
10.0 out of 10, Exceptional, (1)
Bentley Brook: Elevate Your Winter Thrills with Premier Ski-In/Ski-Out Luxury
Bentley Brook: Elevate Your Winter Thrills with Premier Ski-In/Ski-Out Luxury
10.0 out of 10, Exceptional, (1)
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
10.0 out of 10, Exceptional, (1)
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Bentley Brook at Jiminy Peak ^ Studio
Bentley Brook at Jiminy Peak ^ Studio
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Slope-Side Ski-in Ski-Out: Bentley Brook Resort
Slope-Side Ski-in Ski-Out: Bentley Brook Resort
Cozy and large 2 Bedroom 2 Full Bath ski in, ski out condo Unit with balcony.
Cozy and large 2 Bedroom 2 Full Bath ski in, ski out condo Unit with balcony.
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.
Other property types in Middlefield
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (860)
The price is SAR 596
SAR 654 total
includes taxes & fees
23 Jun - 24 Jun
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (8)
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.
Frequently asked questions
Recent reviews of Middlefield hotelsExpedia verified reviews
![The Lenox Collection](http://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/663f69c5_y.jpg)
The Lenox Collection
5/5 Excellent
"The propery is gorgeous. So charming. Staff was very friendly. Very nice room with awesome shower, super comfy bed, and quietly efficient air conditioner."
A verified traveler stayed at The Lenox Collection
Posted 11 hours ago
Popular Destinations
More Accommodation Types in Middlefield
- Vacation Homes in Middlefield (260)
- Cottages in Middlefield (71)
- Apartments in Middlefield (70)
- Condo Rentals in Middlefield (46)
- B&B in Middlefield (30)
- Cabin Rentals in Middlefield (24)
- Motels in Middlefield (17)
- Farmstay in Middlefield (13)
- Guest Houses in Middlefield (6)
- Aparthotels in Middlefield (5)
- Chalets in Middlefield (5)
- Inns in Middlefield (4)
- Villas in Middlefield (4)
- Condo Resorts in Middlefield (2)
- Lodges in Middlefield (2)
- Hotels (960)