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Check prices for these dates

Next weekend
20 Jun - 22 Jun
In two weeks
27 Jun - 29 Jun
In one month
11 Jul - 13 Jul
In two months
8 Aug - 10 Aug

Chalets in Pittsfield

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, (2)
"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
Little Longbow Lakefront Chalet
Smart TV, fireplace

Little Longbow Lakefront Chalet

9.4 out of 10, Exceptional, (12)
"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
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, (24)
"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
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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