Castle In Hawaii - Vacation Rentals in Pittsfield State Forest

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From US $1,521

         

10.0 (4 Reviews)

Villa

20 minutes to Jiminy Peak and Bousquet Mountain

• Air Conditioner
• Parking
• TV

• Albany
• New Lebanon

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From US $323

         

10.0 (4 Reviews)

House

Cozy Ski in out Cabin in Berkshire Resort

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Hancock

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From US $237

         

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8.2 (988 Reviews)

Resort

Jiminy Peak Mountain Resort

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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From US $477

         

10.0 (5 Reviews)

Other

NEW RENO Historic Creamery in Berkshires w/hot tub

• Air Conditioner
• Parking
• TV

• Albany
• Canaan

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From US $225

         

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8.6 (1438 Reviews)

Resort

Vacation Village in the Berkshires

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Williamstown

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From US $206

         

New

Other

Historic 1789 Shaker Farmhouse in Berkshires

• Child Friendly

• Albany
• Canaan

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From US $415

         

10.0 (4 Reviews)

Other

1789 Shaker Farmhouse in Berkshires/Hudson Valley

• Air Conditioner
• Parking
• TV

• Albany
• Canaan

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From US $149

         

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8.5 (157 Reviews)

Resort

Jiminy Peak Mountain Resort

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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From US $398

         

10.0 (4 Reviews)

Other

Ski at Historic Stone Church in The Berkshires

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Lanesborough

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From US $197

         

10.0 (3 Reviews)

Other

NEW RENO - Chalet-style farm loft near Tanglewood

• Air Conditioner
• Parking
• TV

• Albany
• Canaan

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From US $202

         

9.8 (12 Reviews)

Other

NEW RENO - Historic Loft w/views of the Berkshires

• Air Conditioner
• Parking
• TV

• Albany
• Canaan

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From US $214

         

New

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1800s Carriage house in Berkshires/Hudson Valley

• Air Conditioner
• Parking
• TV

• Albany
• Canaan

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From US $225

         

10.0 (34 Reviews)

Other

Farm House in Mt. Meadow

• Air Conditioner
• Parking
• Pool

• Albany
• Stephentown

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From US $137

         

10.0 (9 Reviews)

Other

Berkshires SKI JIMINY Charming 4br/2ba, Fireplaces, scr porch Now-5/15/26

• Air Conditioner
• Parking
• Pool

• Albany
• Lebanon Springs

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From US $267

         

9.6 (4 Reviews)

Other

Charming Farmhouse; 2 Bed/2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.

• Air Conditioner
• Parking
• TV

• Massachusetts
• Williamstown

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New

From US $597

         

New

Other

Charming 5-bedroom farmhouse in Lanesborough

• Parking
• TV
• Security/Safety

• Massachusetts
• Lanesborough

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New

From US $150

         

New

Other

Charming & Bright Berkshires Field House

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Massachusetts
• Richmond

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From US $219

         

10.0 (2 Reviews)

Resort

1 Bd - Vacation Village in the Berkshires

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Massachusetts
• Williamstown

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From US $613

         

10.0 (1 Review)

Resort

Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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From US $175

         

10.0 (1 Review)

Resort

Charming 1 Bedroom - 4 Star Resort w/heated pool, gym, wi-fi, lot's more!

• Air Conditioner
• Pool
• TV

• Massachusetts
• Pittsfield

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From US $391

         

9.6 (18 Reviews)

Resort

COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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From US $335

         

9.0 (12 Reviews)

Resort

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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From US $503

         

New

Resort

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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From US $150

         

New

Resort

Vacation Village In The Berkshires 5 Star Resort - Suite B

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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