Winters Vacations Rentals - Vacation Rentals in Hancock Shaker Village

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From US $419

         

10.0 (29 Reviews)

House

Country Living just minutes from Everything!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Pittsfield

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From US $498

         

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10.0 (1 Review)

House

1 Mi to Vineyard Serene Berkshires Country Escape

• Parking
• Pet Friendly
• View

• Massachusetts
• Richmond

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From US $466

         

|

10.0 (27 Reviews)

Bed & Breakfast

Inn at Kenmore Hall

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Richmond

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From US $438

         

10.0 (5 Reviews)

House

Berkshires Colonial on 2 Acres by Evergreen Home

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Richmond

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From US $623

         

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8.0 (2 Reviews)

House

Historic New Lebanon Hideaway on 33 Private Acres!

• Parking
• Accessibility
• Security/Safety

• Albany
• Canaan

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From US $104

         

8.6 (1000 Reviews)

Hotel

Best Western Plus Berkshire Hills Inn & Suites

• Air Conditioner
• Parking
• TV

• Massachusetts
• Pittsfield

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From US $159

         

10.0 (4 Reviews)

House

Idyllic Berkshires Farmhouse

• Air Conditioner
• Parking
• TV

• Massachusetts
• Richmond

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From US $223

         

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New

House

Berkshire Cottage in Gorgeous Setting!

• Air Conditioner
• Parking
• Internet

• Massachusetts
• Richmond

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From US $83

         

New

Apartment

Chalet-style loft on farm near Tanglewood

• Air Conditioner
• TV
• Balcony/Terrace

• Albany
• Canaan

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From US $641

         

10.0 (3 Reviews)

House

Escape to The Berkshires w/Pool by Evergreen Home

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Richmond

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From US $291

         

10.0 (3 Reviews)

House

Mid-Century At Friendly Hills w Guest Passes !

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Pittsfield

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From US $435

         

10.0 (1 Review)

House

Friendly Richmond Cottage with Private Yard

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Richmond

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From US $393

         

10.0 (1 Review)

House

Richmond Ranch w/Hot Tub by Evergreen Home

• Air Conditioner
• Parking
• TV

• Massachusetts
• Richmond

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From US $357

         

9.6 (18 Reviews)

House

Lovely ranch home getaway in The Berkshires- just 6 miles to Tanglewood

• Air Conditioner
• Parking
• TV

• Massachusetts
• Richmond

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From US $488

         

8.8 (9 Reviews)

House

Historic New Lebanon Hideaway on 33 Private Acres!

• Air Conditioner
• Parking
• TV

• Albany
• Canaan

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From US $247

         

8.0 (1 Review)

Apartment

Airy Upstate Getaway with a View

• Air Conditioner
• Parking
• TV

• Albany
• New Lebanon

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From US $235

         

7.0 (2 Reviews)

House

Berkshire Hideaway w/Fire Pit & Playground!

• Air Conditioner
• Parking
• TV

• Albany
• New Lebanon

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From US $292

         

New

House

1 Mi to Vineyard: Serene Berkshires Country Escape

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Richmond

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From US $262

         

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Cottage

Chic Cottage at Richmond Pond

• Parking
• Pet Friendly
• TV

• Massachusetts
• Richmond

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From US $316

         

9.6 (104 Reviews)

House

Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Richmond

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From US $1,615

         

10.0 (8 Reviews)

House

Morning Face - Berkshire estate with heated pool, views and privacy.

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Richmond

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From US $619

         

10.0 (99 Reviews)

House

Modern 4 bedroom lakefront house in The Berkshires.

• Air Conditioner
• Parking
• TV

• Massachusetts
• Richmond

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From US $202

         

10.0 (23 Reviews)

Apartment

Private apartment in beautiful country barn

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Richmond

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From US $326

         

10.0 (12 Reviews)

Apartment

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Richmond

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