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Compare 7 Chalets in Hillsdale with updated reviews, rates, and availability.

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
Main level open space (old setup)

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

9.8 out of 10, Exceptional, (22)
"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! 15 mins to Ski Butternut.
Little Longbow Lakefront Chalet
Aerial view

Little Longbow Lakefront Chalet

10.0 out of 10, Exceptional, (9)
"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
Lakefront w/Dock! Family Friendly Amenities, Close to skiing and Hudson, NY
Terrace/patio

Lakefront w/Dock! Family Friendly Amenities, Close to skiing and Hudson, NY

8.8 out of 10, Excellent, (6)
"We very much enjoyed our time spent at Eagles Nest playing pickleball, ping pong, time at the pool and using the various boating equipment. Just beware as you may encounter a water snake or 2 but they are timid and we continued enjoying the dock activities such as fishing, kayaking, paddleboating or just laying on the floating mat. The kitchen and laundry room were extremely well appointed as was each bedroom with it's own tv. The lake is also an extremely quiet body of water. The one slight...
Lakefront w/Dock! Family Friendly Amenities, Close to skiing and Hudson, NY
Berkshire Chalet: Walk to Lenox. Mobility friendly, Amazing Views.Dog Friendly!
garden view of the back of the cabin, with the deck

Berkshire Chalet: Walk to Lenox. Mobility friendly, Amazing Views.Dog Friendly!

8.8 out of 10, Excellent, (3)
"We really enjoyed our stay at this adorable A frame home. The home was a quick drive to tanglewood and the views were beautiful. The owner was very communicative and prompt with answering any questions. "
Berkshire Chalet: Walk to Lenox. Mobility friendly, Amazing Views.Dog Friendly!
Chic Stream-side Chalet with Mountain View and Vintage Designer Furnishings
Terrace/patio

Chic Stream-side Chalet with Mountain View and Vintage Designer Furnishings

Chic Stream-side Chalet with Mountain View and Vintage Designer Furnishings
SRC-Hudson Valley/Berkshires Cultural Corridor
Property grounds

SRC-Hudson Valley/Berkshires Cultural Corridor

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

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 Hillsdale

Micosta Leisure Inn
Terrace/patio

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (91)
"Second time I’ve stayed. Nice place. Owner very communicative. Good prices. "
The price is SAR 443
SAR 478 total
includes taxes & fees
1 Feb - 2 Feb
Micosta Leisure Inn
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (234)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is SAR 563
SAR 860 total
includes taxes & fees
10 Jan - 11 Jan
Berkshire Village Carriage House - Super Private!!
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
The Cabin Overlooking Chloe's Lake

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very Good, (42)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is SAR 469
SAR 544 total
includes taxes & fees
12 Jan - 13 Jan
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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.