Top Winter Vacations - Vacation Rentals in Magnolia Bluffs Casino

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From US $451

         

10.0 (41 Reviews)

House

Cheerful 3-bedroom cottage with woodstove

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Sheffield

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From US $259

         

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10.0 (5 Reviews)

House

The Mill River Cabin with Fireplace and River View!

• Parking
• Pet Friendly
• Accessibility

• Massachusetts
• Mill River

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From US $176

         

9.8 (38 Reviews)

Bed & Breakfast

Wilder House Berkshires

• Air Conditioner
• Parking
• Balcony/Terrace

• Massachusetts
• Sheffield

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From US $363

         

10.0 (34 Reviews)

House

Little House in the Woods by Evergreen Home

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Sheffield

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From US $235

         

|

9.5 (50 Reviews)

Bed & Breakfast

Wilder House Berkshires

• Air Conditioner
• Parking
• View

• Massachusetts
• Sheffield

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From US $228

         

10.0 (15 Reviews)

Cottage

The Blue Elm - A Historic Berkshire Cottage

• Air Conditioner
• Parking
• TV

• Massachusetts
• Ashley Falls

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From US $217

         

New

House

Whitney by AvantStay Private Berkshires Estate

• Parking
• Pet Friendly
• Security/Safety

• Massachusetts
• Sheffield

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From US $194

         

10.0 (6 Reviews)

Apartment

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

• Air Conditioner
• Parking
• TV

• Massachusetts
• Sheffield

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From US $265

         

9.6 (44 Reviews)

Cabin

'The Mill River Cabin’ w/Fireplace & River View!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Mill River

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From US $437

         

8.6 (14 Reviews)

House

Whitney by AvantStay | Private Berkshires Estate

• Parking
• Pet Friendly
• TV

• Massachusetts
• Sheffield

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From US $315

         

10.0 (180 Reviews)

House

“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Sheffield

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From US $700

         

10.0 (52 Reviews)

House

Gorgeous Sheffield Home in Heart of Berkshires

• Air Conditioner
• Parking
• Balcony/Terrace

• Massachusetts
• Sheffield

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From US $469

         

10.0 (29 Reviews)

House

12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room

• Air Conditioner
• Parking
• TV

• Massachusetts
• Sheffield

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From US $658

         

10.0 (21 Reviews)

House

Restful pastoral, kids-friendly house w/gardens, views, swimming pool, sauna

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Southfield

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From US $326

         

10.0 (21 Reviews)

House

Konkapot Cottage, Pastoral Bliss With Wide Views

• Air Conditioner
• Parking
• TV

• Massachusetts
• Southfield

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From US $560

         

10.0 (15 Reviews)

House

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Sheffield

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From US $387

         

10.0 (6 Reviews)

House

Peaceful and Private Setting

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Sheffield

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From US $729

         

10.0 (3 Reviews)

House

Majestic Mountain Side Sheffield/Great Barrington/SKI

• Air Conditioner
• Parking
• TV

• Massachusetts
• Sheffield

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From US $259

         

10.0 (2 Reviews)

House

COME STAY AT THE SHEFFIELD CHALET!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Sheffield

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From US $475

         

10.0 (1 Review)

House

Modern Dairy Barn with Ample Natural Light and 2 Living Rooms!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Sheffield

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From US $335

         

10.0 (1 Review)

House

Meadow Top Cottage: Countryside Cottage on 72 Acres

• Air Conditioner
• Parking
• TV

• Great Barrington
• New Marlborough

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From US $252

         

10.0 (1 Review)

House

South Berkshire Barn Apartment with Stunning Views

• Air Conditioner
• Parking
• Security/Safety

• Massachusetts
• Sheffield

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From US $157

         

10.0 (1 Review)

House

Open for ski season or full time rental. Book 2024 Summer Season now for less.

• Air Conditioner
• Parking
• TV

• Massachusetts
• Sheffield

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From US $368

         

9.8 (7 Reviews)

House

Berkshires Walk to Brewery or Distillery with Peloton!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Sheffield

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