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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 5 Chalets in Pittsfield with updated reviews, rates, and availability.

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
3 bedrooms, desk, iron/ironing board, travel crib

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.

9.8 out of 10, Exceptional, (23)
"Short couples getaway to recharge. The house was perfect and the wood stove kept the house toasty through the cold windy stay. HINT: coming from NY/NJ, buy your groceries as you pass through Great Barrington and save that extra trip."
Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
Little Longbow Lakefront Chalet
Smart TV, fireplace

Little Longbow Lakefront Chalet

9.2 out of 10, Wonderful, (10)
"The location was great. Very peaceful. Not far from Lee, Lenox or Great Barrington. The house was very cute and as described. Will absolutely stay again. "
Little Longbow Lakefront Chalet
Private Luxury Chalet-Hot Tub-Heated Pool-Firepit-Game Rooms-Fits 16 people
Outdoor spa tub

Private Luxury Chalet-Hot Tub-Heated Pool-Firepit-Game Rooms-Fits 16 people

10.0 out of 10, Exceptional, (1)
"Rimon and Sallie's place is fantastic. Very clean with everything we needed for our stay. The kids were able to have their own separate space, and the common areas were great for food prep and sitting down for meals. The kids loved the hot tub and were in 3 separate times (even in the freezing temps!).The house is very private on a beautiful road, and is a short drive to Troy, Albany, etc. We had a great dinner at Hill Creek Tavern 5 minutes from the house. I would absolutely recommend this...
Private Luxury Chalet-Hot Tub-Heated Pool-Firepit-Game Rooms-Fits 16 people
SRC-Hudson Valley/Berkshires Cultural Corridor
Exterior

SRC-Hudson Valley/Berkshires Cultural Corridor

SRC-Hudson Valley/Berkshires Cultural Corridor
Majestic Lake Front Chalet
Living area

Majestic Lake Front Chalet

2.0 star property
Majestic Lake Front Chalet
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 Pittsfield

Hancock Village Inn at Jiminy Peak
Snow and ski sports

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is SAR 2,059
SAR 3,882 total
includes taxes & fees
28 Mar - 29 Mar
Hancock Village Inn at Jiminy Peak
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Exterior

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (56)
"Perfect location and accommodation for my family. The home was as described. I would recommend it. The property owner was easy to work with. "
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
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.