Berkshires Vacation Rentals

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Serenity Stone Cottage on 5 beautiful secluded acres in a historic town

  1. Massachusetts,
  2. Berkshires,
  3. Shelburne Falls Vacation Home Rentals
— Property 190201
Berkshires cottage rental - Stone facade at cottage entrance
3 Bedrooms, Sleeps 7
  • Cottage
  • 2 Bathrooms
  • mountain, town
  • washing machine
Rates per property (USD)
$980/week
 
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Under 1 mi. to Jiminy Peak - Cozy 3BR/2bath - Credit Cards accepted

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Vacation Home Rentals
— Property 145582
Berkshires house rental - Fresh snow and another 8 inches just arrived
3 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms
  • mountain, rural
  • washing machine
Rates per property (USD)
$200 - $450/night
 
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Great Cottage for Ski Weekend!

  1. Massachusetts,
  2. Berkshires,
  3. Otis Vacation Home Rentals
— Property 124984
Berkshires house rental
3 Bedrooms, Sleeps 7
  • House
  • 3 Bathrooms
  • mountain, rural
  • washing machine
 
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Ideal Lenox, Massachusetts home, near all Berkshire cultural attractions

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 225362
Berkshires house rental - Front of house
3 Bedrooms, Sleeps 7
  • House
  • 3 Bathrooms
  • mountain, rural
  • air-conditioning
Rates per property (USD)
$230 - $265/night
$1,650/week
$5,700/month
 
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Charming Lakeview Home Amid Berkshire Beauty, Arts

  1. Massachusetts,
  2. Berkshires,
  3. Monterey Vacation Home Rentals
— Property 137922
Berkshires cottage rental - Charming cottage overlooking lake and wetlands
3 Bedrooms, Sleeps 8
  • Cottage
  • 2 Bathrooms
  • lake, mountain
  • air-conditioning
Rates per property (USD)
$175 - $225/night
$1,200 - $1,600/week
$1,150 - $6,400/month
 
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Quaint Three Bedroom House in the Berkshire Mountains Five-minute Walk from Will

  1. Massachusetts,
  2. Berkshires,
  3. Williamstown Vacation Home Rentals
— Property 311008
Berkshires house rental
3 Bedrooms, Sleeps 8
  • House
  • 1 Bathroom
  • mountain, village
  • washing machine
 
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Classic Modern home, light & bright.

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 115280
Berkshires house rental - Front view of house
3 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms
  • mountain, town
  • air-conditioning
Rates per property (USD)
$1,200/week
 
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Chapin's Sugar Hill Farm

  1. Massachusetts,
  2. Berkshires,
  3. Chesterfield Vacation Home Rentals
— Property 148210
Berkshires farmhouse rental
3 Bedrooms, Sleeps 8
  • Farmhouse
  • mountain, rural
  • washing machine
Rates per property (USD)
$1,400/week
 
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Jiminy Peak Mountainside Condo

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Vacation Home Rentals
— Property 224073
Berkshires condo rental
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • mountain, resort
  • swimming pool
Rates per property (USD)
$8,000/month
 
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Perfect location - multi-level ski condo/townhouse on Jiminy Peak

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Vacation Home Rentals
— Property 209346
Berkshires condo rental
3 Bedrooms, Sleeps 9
  • Condo
  • 2 Bathrooms
  • mountain, resort
  • swimming pool
 
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Glorious Views

  1. Massachusetts,
  2. Berkshires,
  3. Monterey Vacation Home Rentals
— Property 223821
Berkshires house rental - House
3 Bedrooms, Sleeps 8
  • House
  • 4 Bathrooms
  • mountain, rural
  • air-conditioning
Rates per property (USD)
$12,000/month
 
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SPECIAL OFFER! Ski Season Special! (January 19 - March 31)

Charming Berkshires lakefront house near Jiminy Peak with beautiful views

  1. Berkshires,
  2. Jiminy Peak,
  3. Cheshire Vacation Home Rentals
— Property 122780
Berkshires house rental - The house from the lake, in fall
3 Bedrooms, Sleeps 7
  • House
  • 1 Bathroom
  • lake, mountain
  • air-conditioning
Rates per property (USD)
$175 - $200/night
$850 - $1,100/week
 
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Special Offer

Four Season Berkshires Vacation Home

  1. Massachusetts,
  2. Berkshires,
  3. Otis Vacation Home Rentals
— Property 112829
Berkshires house rental - The cabin in the Spring
3 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • lake, mountain
  • swimming pool
 
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Breathtaking Berkshire Rental -

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Vacation Home Rentals
— Property 105168
Berkshires condo rental
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • mountain, rural
  • swimming pool
 
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Gateway To The Berkshires

  1. Massachusetts,
  2. Berkshires,
  3. Sheffield Vacation Home Rentals
— Property 211271
Berkshires house rental - The Front of the House
3 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • mountain, rural
  • accept credit card
Rates per property (USD)
$175 - $250/night
$950 - $1,500/week
$1,800 - $2,500/month
 
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Beautiful Bungalow Beside Babbling Brooks

  1. Massachusetts,
  2. Berkshires,
  3. Becket Vacation Home Rentals
— Property 111135
Berkshires house rental - The House and Deck in the Winter
3 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms, 1 Half Bath
  • lake, mountain
  • air-conditioning
 
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Luxurious Secluded Hilltop Carriage House

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 100299
Berkshires house rental - Front view of the House
3 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms
  • mountain, river
  • air-conditioning
 
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Elegant Berkshires Home with Mountain Views

  1. Massachusetts,
  2. Berkshires,
  3. Williamstown Vacation Home Rentals
— Property 223120
Berkshires house rental - Great room with mountain views and grand piano
3 Bedrooms, Sleeps 8
  • House
  • 3 Bathrooms
  • mountain, village
  • washing machine
Rates per property (USD)
$175 - $325/night
$1,500 - $2,100/week
$3,500 - $5,000/month
 
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Golf
Ski

A house for all seasons in the Berkshires

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 152718
Berkshires house rental
3 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms
  • mountain, village
  • washing machine
Rates per property (USD)
$1,250/month
 
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Log Home Nestled in the Woods

  1. Massachusetts,
  2. Berkshires,
  3. Monterey Vacation Home Rentals
— Property 162300
Berkshires chalet rental - Summer at the Chalet
3 Bedrooms, Sleeps 7
  • Chalet
  • 2 Bathrooms
  • mountain, rural
  • air-conditioning
Rates per property (USD)
$1,500/week
 
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Charming, Berkshires Ski/Lakehouse....country setting...only 6 miles to Gt Barr.

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 109882
Berkshires house rental - Front of House
3 Bedrooms, Sleeps 5
  • House
  • 1 Bathroom, 1 Half Bath
  • lake, mountain
  • washing machine
Rates per property (USD)
$200 - $250/night
$1,400 - $1,800/week
$4,000/month
 
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Sunny Contemporary, Views, Private, near Events

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 116237
Berkshires house rental - view from parking area
3 Bedrooms, Sleeps 7
  • House
  • 2 Bathrooms
  • mountain, rural
  • washing machine
 
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Spacious Contemporary - Country Mtns - minutes from Town - All Seasons.

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 139379
Berkshires house rental
3 Bedrooms, Sleeps 7
  • House
  • 3 Bathrooms
  • mountain, town
  • air-conditioning
 
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Jem's Berkshire Rental

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 152703
Berkshires house rental - House view
3 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms, 1 Half Bath
  • mountain, town
  • accept credit card
Rates per property (USD)
$350 - $500/night
$2,000 - $3,000/week
 
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Private Large Contemporary Victorian with Pool

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 100415
Berkshires house rental - pool and deck
3 Bedrooms, Sleeps 6
  • House
  • 3 Bathrooms
  • mountain, rural
  • swimming pool
 
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Jiminy Peak 4-Level Deluxe Condo - ski resort.- one mile off the mountain!

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Vacation Home Rentals
— Property 101805
Berkshires condo rental - Outside view on 24 ft. deck with Weber Gas Grill
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • mountain, resort
  • swimming pool
Rates per property (USD)
$600 - $750/night
$2,500/week
$5,000 - $7,000/month
 
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Jiminy Peak mountainside condo for all seasons

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Vacation Home Rentals
— Property 117964
Berkshires condo rental
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • mountain, resort
  • swimming pool
 
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Family Farmhouse Tudor with 6 Acres

  1. Massachusetts,
  2. Berkshires,
  3. Pittsfield Vacation Home Rentals
— Property 179777
Berkshires farmhouse rental - Pittsfield / Richmond border Tudor
3 Bedrooms, Sleeps 8
  • Farmhouse
  • 2 Bathrooms
  • mountain, village
  • accept credit card
Rates per property (USD)
$1,800 - $2,000/week
$4,000 - $6,500/month
 
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Hillside Hideaway with Trout Streams, near all Berkshire attractions

  1. Massachusetts,
  2. Berkshires,
  3. Becket Vacation Home Rentals
— Property 103847
Berkshires house rental
3 Bedrooms, Sleeps 6
  • House
  • 1 Bathroom
  • mountain, river
  • washing machine
 
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Berkshires Comfort, Convenience & Privacy

  1. Massachusetts,
  2. Berkshires,
  3. Southfield Vacation Home Rentals
— Property 184708
Berkshires house rental
3 Bedrooms, Sleeps 6
  • House
  • 3 Bathrooms
  • mountain, resort
  • swimming pool
Rates per property (USD)
$1,400 - $2,300/week
 
Contact the Owner
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