Photo by Elizabeth Massa Peroulakis

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Compare 4 Chalets in Monterey with updated reviews, rates, and availability.

Little Longbow Lakefront Chalet
Golf
Little Longbow Lakefront Chalet
10.0 out of 10, Exceptional, (8)
"My husband, dog and I had a Monday-Friday stay at Jaclyn's house on the water. We wanted a place that felt private but wasn't far from grocery stores, restaurants, and hiking. This place delivered! We did go out for a paddle on the little pond and saw some little fish and freshwater clam shells broken by a hungry creature. The swimming area is a 5 minute walk from the house. I sat out by the water to read in the shade and the sitting area is lovely and there were no bugs. They seem to spray the...
Little Longbow Lakefront Chalet
Berkshires Hilltop Retreat w Magic View! Peak Fall Foliage Weekends Available!
Main level open space (old setup)
Berkshires Hilltop Retreat w Magic View! Peak Fall Foliage Weekends Available!
9.8 out of 10, Exceptional, (21)
"Beautiful well kept house in the Berkshires, great view and layout. Close to amazing nature and Great Barrington if you need anything. Wonderful trip!"
Berkshires Hilltop Retreat w Magic View! Peak Fall Foliage Weekends Available!
Nature retreat by Brook
Rustic contemporary with field stone foyer and working fireplace
Nature retreat by Brook
Nature retreat by Brook
SRC-Hudson Valley/Berkshires Cultural Corridor
Property grounds
SRC-Hudson Valley/Berkshires Cultural Corridor
SRC-Hudson Valley/Berkshires Cultural Corridor
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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 Monterey

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Lake-we provide kayaks and a canoe!
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (205)
"My stay was shorter than I had planned but the few days I was here was so relaxing. First of all, the bed is so comfortable, I slept like a baby. Very quiet area. Nice to walk around with my dogs and explore. The cottage was nicely outfitted with any needs you might have. Beautiful time of year to stay here! I cannot wait to go back. I also want to say I appreciate that they allowed my two dogs. My dogs are very well behaved, and I travel with them quite often. Not all places allow this, so I...
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!
Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (15)
"Our mix of family and friends had a wonderful time at your home over the Labor Day weekend. The space was clean, spacious and beautiful. The property had plenty for everyone to do. We will definitely be booking again. "
Amore Estate - beautiful room with many places to explore and relax in.
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
9.8 out of 10, Exceptional, (36)
"Communication with property manager was seamless, and above any previous interactions I have ever had. Great place. Well maintained. Clean. Stocked with basic kitchenware and cleaning material. Great Wifi. Tennis Court was such a nice bonus. Would 100% (and will likely) stay here again!"
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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.