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$450

3 BR / 3 BA / Sleeps 6

New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood) - Berkshires vacation rentals
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$450

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New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

Richmond house
3 BR / 3 BA / Sleeps 6 | Quick view

Details

Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed idyllic swimming pool …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

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$172

3 BR / 2 BA / Sleeps 6

Charming get-a-way in Great Barrington Berkshires - Berkshires vacation rentals
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$172

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Charming get-a-way in Great Barrington Berkshires

Great Barrington house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

Charming get-a-way in a friendly residential neighborhood in Great Barrington. Our home is sunny and bright, with an eat-in-kitchen, casual living room and dining area with beautiful picture windows, three comfortable bedrooms, and 1.5 bathrooms. Fully furnished with an eclectic mix of modern and older finds from the …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children

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$357

6 BR / 5 BA / Sleeps 12

Elegant 6000+Sf Luxury Estate on 13+ Park - Berkshires vacation rentals
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$357

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Elegant 6000+Sf Luxury Estate on 13+ Park

Great Barrington house
6 BR / 5 BA / Sleeps 12 | Quick view

Details

This Elegant Luxury Estate offers 6000+ SF of Living Space on 13+ park-like, sunny acres located within only minutes from the downtown Great Barrington. This fantastic home offers 5 Bedrooms, 4.5 bathrooms, sweeping dual staircase ending with the magnificent open gallery, the kitchen offers the magnificent, high end …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$242

3 BR / 2 BA / Sleeps 6

Spacious comfortable mid-century modern near town - Berkshires vacation rentals
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$242

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Spacious comfortable mid-century modern near town

Lenox house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

In the heart of Lenox, this 2 BR plus study (can be used as a 3BR) house offers the best of both worlds. On nearly 2 park-like acres, the house is a peaceful place for rest and relaxation. But there's much to do nearby. The town center of Lenox is within easy walking distance so you'll be close to restaurants, shops…
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$188

4 BR / 2 BA / Sleeps 10

Lakefront Berkshires Ski/Summer House, Great Views - Berkshires vacation rentals
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$188

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Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house
4 BR / 2 BA / Sleeps 10 | Quick view

Details

Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or lounge on the deck and …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$250

2 BR / 1 BA / Sleeps 5

Lenox Walk to Town / Tanglewood - Berkshires vacation rentals
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$250

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Lenox Walk to Town / Tanglewood

Lenox cottage
2 BR / 1 BA / Sleeps 5 | Quick view

Details

This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows and the lush forest …
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$300

6 BR / 3 BA / Sleeps 11

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$300

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Beautiful Colonial in Secluded Berkshires

Becket house
6 BR / 3 BA / Sleeps 11 | Quick view

Details

Enjoy the Fall in our New England farmhouse! Cross country ski at Canterbury Farms, only 5 minutes away! Beautifully restored Colonial historical farmhouse (1790) with almost 2 acres of lawn for playing croquet and hanging out in the sun. There is a small pond (unfenced) for frogs and birds. Large screened in …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Central heating
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$375

2 BR / 2 BA / Sleeps 6

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$375

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July4th Berkshires/James Taylor/2Bed Presidential

Lee condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it! Tanglewood/Lenox is …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$249

2 BR / 2 BA / Sleeps 8

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$249

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Wyndham Bentley Brook

Hancock condo
2 BR / 2 BA / Sleeps 8 | Quick view

Details

Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking and horseback riding, Tanglewood …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Fireplace
  • Suitable for children

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