Winters Vacations Rentals - Vacation Rentals in Pittsfield State Forest

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From US $527

         

9.6 (17 Reviews)

Condo

3 BR+ 4level WINTER SKI RENTALn LOOKING 4 SEASONAL RENTERn 1 MILE OFF OF JIMINEY

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Lanesborough

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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 $190

         

10.0 (7 Reviews)

RV Rental

Huttopia Berkshires

• Parking
• Pet Friendly
• Pool

• New York
• Brainard

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From US $343

         

10.0 (129 Reviews)

Cabin

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

• Air Conditioner
• Parking
• TV

• Massachusetts
• Pittsfield

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From US $494

         

10.0 (2 Reviews)

Apartment

5 Bed/3 bath Apt Near Jiminy Peak Berkshires

• Air Conditioner
• Parking
• Pet Friendly

• Albany
• Stephentown

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From US $134

         

|

9.0 (775 Reviews)

Cabin

Berkshire Mountain Lodge

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Pittsfield

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From US $266

         

10.0 (97 Reviews)

House

Hearts Desire is a furnished whole house in a small, colorful garden center.

• Air Conditioner
• Parking
• TV

• Massachusetts
• Lanesborough

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From US $279

         

|

10.0 (2 Reviews)

Apartment

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

• Pool
• Accessibility
• Security/Safety

• Massachusetts
• Hancock

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From US $123

         

|

8.8 (2168 Reviews)

Condo

Vacation Village in the Berkshires

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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From US $680

         

10.0 (63 Reviews)

House

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

• Air Conditioner
• Parking
• TV

• Massachusetts
• Pittsfield

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From US $418

         

10.0 (41 Reviews)

Condo

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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From US $379

         

10.0 (38 Reviews)

House

Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

• Parking
• View
• Ocean View

• Albany
• Stephentown

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From US $379

         

10.0 (36 Reviews)

Condo

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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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 $236

         

10.0 (23 Reviews)

Apartment

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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From US $1,047

         

10.0 (16 Reviews)

House

Hancock Village Inn Near Jiminy Peak

• Air Conditioner
• Parking
• TV

• Massachusetts
• Pittsfield

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From US $380

         

10.0 (14 Reviews)

Condo

UNIQUE - 1BR Country Condo @ Jiminy Peak

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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From US $303

         

10.0 (14 Reviews)

Condo

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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From US $644

         

10.0 (13 Reviews)

Condo

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Hancock

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From US $409

         

10.0 (13 Reviews)

House

Woodland 5-BR Retreat 5-Min to Jiminy Peak

• Parking
• Pet Friendly
• Pool

• Massachusetts
• Pittsfield

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From US $856

         

10.0 (11 Reviews)

House

Breathtaking Post & Beam minutes from Jiminy Peak, Williamstown, Lenox & hiking

• Air Conditioner
• Parking
• TV

• Massachusetts
• Lanesborough

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From US $654

         

10.0 (11 Reviews)

House

Hidden Oasis in the Mountains by Evergreen Home

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Pittsfield

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From US $423

         

10.0 (8 Reviews)

House

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Lanesborough

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From US $236

         

10.0 (8 Reviews)

Apartment

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

• Parking
• Pool
• TV

• Massachusetts
• Hancock

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