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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach
3 bedrooms, desk, iron/ironing board, travel crib

Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach

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."
Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach
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
28 Acre Private Luxury Chalet-Hot Tub-Heated Pool-Game Rooms-16 ppl-pet friendly
Outdoor spa tub

28 Acre Private Luxury Chalet-Hot Tub-Heated Pool-Game Rooms-16 ppl-pet friendly

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...
28 Acre Private Luxury Chalet-Hot Tub-Heated Pool-Game Rooms-16 ppl-pet friendly
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
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,810 total
includes taxes & fees
5 May - 6 May
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, (140)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Dancing Horse Lodge
Fridge, microwave, oven, stovetop

Dancing Horse Lodge

9.6 out of 10, Exceptional, (41)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse 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.