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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 35 Resorts in Plainfield with updated reviews, rates, and availability.

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)
"Stay was perfect all you need "
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
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
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!
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, (16)
"Perfect for a weekend of skiing with the family."
COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE
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)
"We enjoyed staying at this clean, quiet, and comfy property. Close to so many beautiful spots! Only minutes to both New York and Vermont!"
Lg 1 Bd - Vacation Village in the Berkshires
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
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
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 - 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
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
Bentley Brook at Jiminy Peak ^ Studio
Exterior

Bentley Brook at Jiminy Peak ^ Studio

Bentley Brook at Jiminy Peak ^ Studio
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, 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
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Dining

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
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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Other property types in Plainfield

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1813)
"The property was clean and the staff very accommodated."
The price is AED 299
AED 375 total
includes taxes & fees
10 Jun - 11 Jun
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (930)
"Out dated not many resort like options "
The price is AED 526
AED 587 total
includes taxes & fees
29 May - 30 May
Jiminy Peak Mountain Resort
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (13)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
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

What is Plainfield like for a resort vacation?
You deserve a break, and a resort is just the place to pamper yourself with the amenities and services you need for a relaxing time in Plainfield. One of the comfortable resorts in the area might be just what you’re looking for, whether you’re hoping for an amazing pool, a state-of-the-art fitness center, or nightly entertainment options.
What's the best resort for my stay in Plainfield?
Our highest-rated resorts around Plainfield: All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. - 19.2 mi (30.9 km) from Plainfield. Features a sauna. Bentley Brook the perfect home base for exploring nearby Berkshire County - Ski resort. 19.2 mi (30.9 km) from Plainfield. Has ski-in/ski-out access, a sauna, and a fitness center. Bentley Brook the perfect home base for exploring nearby Berkshire County - Ski resort. 19.2 mi (30.9 km) from Plainfield. Enjoy the ski-in/ski-out access, sauna, and fitness center. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort. 19.3 mi (31 km) from Plainfield. Amenities include ski-in/ski-out access, a fitness center, and a garden.
What can I do in Plainfield?
If you’re interested in local sights, Swift River, Ashfield Lake, and Berkshire East Ski Resort are some places to visit nearby. In the area, other attractions include Thunderbolt Mountain Coaster and Zoar Outdoor/Deerfield Valley Canopy Tours.
What's the weather like in Plainfield?
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 Plainfield are January, March, November, and February, with each month seeing an average of 9 inches of snowfall.
What's the best way to get to and around Plainfield?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 20.1 mi (32.4 km) from the city center. Otherwise, you can search for flights to Westfield, MA (BAF-Barnes Municipal), which is 26 mi (41.9 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.