Berkshires Rentals I Berkshires Vacation Rentals by Owner

Privacy on scenic acreage with brook - 3 bedrooms, 2 1/2 baths- sleeps up to 12. Enjoy the scenic views and serenity or explore the local waterways by launching your canoe on the brook running thro...

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• Type: Home
• Max Cap.: 12
• Bedrooms: 3
• Rate: $100 to $250 Per Night

A cozy retreat nestled in white pines. Situated on 4.8 acres, FenCroft Cottage may be rented seperately or (for very large parties) in conjunction with OverBrook. Nestled among white pines with acces...

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• Type: Guest House
• Max Cap.: 8
• Bedrooms: 2
• Rate: $100 to $250 Per Night

Coming Soon! Large in-town townhouse (approx. 1,900 sf), half of what was once a carriage house (ca. 1890). Steps from Main Street, Stockbridge, across the street from the Red Lion Inn in town cent...

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• Type: Townhouse
• Max Cap.: 10
• Bedrooms: 3
• Rate: Over $250 Per Night

Available for August. One bedroom 2nd floor apartment in Victorian Home. Private entrance. Living room, Sun/dining room, bright kitchen, full bath. No pets. No smoking in home or on premises. Air-cond...

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• Type: Home
• Max Cap.: 2
• Bedrooms: 1
• Rate: $99 or Less Per Night

This is a light-filled and airy home with several sets of double glass doors leading to the surrounding meadows. There are three bedrooms, including a luxuriously sized master suite with sliding do...

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• Type: Home
• Max Cap.: 8
• Bedrooms: 3
• Rate: Over $250 Per Night

Rent a comfortable 1840 farmhouse in the Berkshires set on 26 acres. The house has 2 living rooms, dining room, sun room, 5 bedrooms, 2 ½ baths, new eat-in kitchen, laundry room, games ro...

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• Type: Home
• Max Cap.: 12
• Bedrooms: 5
• Rate: Over $250 Per Night

Imagine your own fully furnished Log Cabin on 1.5 acres in a lake community. Just 2.5 hours from NYC and Boston! This 3 BR, 2 BA cabin sleeps 6. It has a living room, den, fully equiped kitchen, laun...

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• Type: Cabin
• Max Cap.: 6
• Bedrooms: 3
• Rate: $100 to $250 Per Night

SPECTACULAR CONTEMPORARY SALTBOX in the Berkshires on 18 wooded acres down the road from Jacob's Pillow, the internationally famous dance theater center in Becket, Mass. Tanglewood and all the other c...

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• Type: Home
• Max Cap.: 6
• Bedrooms: 3
• Rate: Over $250 Per Night

A charming and comfortable contemporary log home with views. The house is a very short walk to Jacob's Pillow and relatively close to Tanglewood, theaters, restaurants and the many cultural and sceni...

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• Type: Home
• Max Cap.: 6
• Bedrooms: 3
• Rate: $100 to $250 Per Night

Rental unit is a compact studio apartment over 2-car garagw at a secluded woodland home at Mass.-NY border, 10 miles from Tanglewood. Private entrance from garden area. Air-conditioned, with refrigera...

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• Type: Home
• Max Cap.: 2
• Bedrooms: 1
• Rate: $100 to $250 Per Night

This is a beautiful two story contemporary home 2 miles from Tanglewood, right off Route 183. There is also a detached artst's studio that is included in the rental fee....

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• Type: Yachts
• Max Cap.: 5
• Bedrooms: 4
• Rate: $100 to $250 Per Night

Gorgeous eontemporary on secluded 2.5 acres just outside of town of Gt. Barrington, 10-15 minutes from Butternut and Catamount. Beautiful woodwork, soaring ceilings, 3 sliding glass doors, huge terra ...

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• Type: Home
• Max Cap.: 7
• Bedrooms: 3
• Rate: $100 to $250 Per Night

DELUXE NEW HOME + 2 MASTER SUITES + TANGLEWOOD AREA--5 Bedrooms-5 Bathrooms Brand new 3,400 sq ft Lee home in a private lake community, Berkshires. Situated on 4 wooded acres on a quiet country road w...

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• Type: Home
• Max Cap.: 12
• Bedrooms: 5
• Rate: Over $250 Per Night

New custom home in the Berkshires with deeded beach rights to Beachwood Beach on the Stockbridge Bowl and less than 2 miles from Tanglewood. All the cultural and recreational attractions of the Berks...

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• Type: Home
• Max Cap.: 14
• Bedrooms: 5
• Rate: $100 to $250 Per Night

Fabulous home in the beautiful and historic Berkshire Hills of Western Mass. 3-4 bedrooms, two bathrooms, rustic southwestern-style post & beam interior on 11 wooded acres plus 2 acre lawn with great...

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• Type: Home
• Max Cap.: 6
• Bedrooms: 4
• Rate: $100 to $250 Per Night

This is a lovely, newly remodeled 4 bedroom, 3 bath home on a country road in the town of Richmond which is a small town situated in the West Stockbridge, Stockbridge, Lennox area. Other close-by tow...

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• Type: Home
• Max Cap.: 8
• Bedrooms: 4
• Rate: $100 to $250 Per Night

Luxury two bedroom ~ two bath ~ condo with full kitchen and washer / dryer is available many weeks this year. Please inquire about your desired week to stay. Thank you....

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• Type: Condo
• Max Cap.: 6
• Bedrooms: 2
• Rate: $99 or Less Per Night