Berkshires Vacation Rentals

21 Properties, sort by: 
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Williamstown Contemporary Carriage Barn

  1. Massachusetts,
  2. Berkshires,
  3. Williamstown Vacation Home Rentals
— Property 201243
Williamstown barn rental - Open layout -- great for entertaining!
2 Bedrooms, Sleeps 5
  • Barn
  • 1 Bathroom
  • town, village
  • air-conditioning
View Property Details Contact the Owner

Tree Peepers Getaway/New Construction/4bd3.5bth

  1. Massachusetts,
  2. Berkshires,
  3. West Stockbridge Vacation Home Rentals
— Property 179961
West Stockbridge house rental
4 Bedrooms, Sleeps 8
  • House
  • 3 Bathrooms, 1 Half Bath
  • mountain, village
  • air-conditioning
Rates per property (USD)
$2,000 - $2,500/week
$5,500 - $8,500/month
View Property Details Contact the Owner

Newly renovated country estate w/panoramic mountain views-over 130 private acres

  1. Massachusetts,
  2. Berkshires,
  3. Sandisfield Vacation Home Rentals
— Property 178114
Sandisfield farmhouse rental - Wrap-around porch perfect for entertaining!
5 Bedrooms, Sleeps 10
  • Farmhouse
  • 3 Bathrooms
  • mountain, rural
  • air-conditioning
Rates per property (USD)
$300 - $750/night
$1,800 - $2,750/week
$5,000 - $8,000/month
View Property Details Contact the Owner

Berkshires Comfort, Convenience & Privacy

  1. Massachusetts,
  2. Berkshires,
  3. Southfield Vacation Home Rentals
— Property 184708
Southfield condo rental
3 Bedrooms, Sleeps 4
  • Condo
  • 3 Bathrooms
  • beach, resort
  • swimming pool
Rates per property (USD)
$200/night
View Property Details Contact the Owner

Fabulous Home with Pool & Hot Tub ~ July and August Special Offer

  1. Massachusetts,
  2. Berkshires,
  3. Stockbridge Vacation Home Rentals
— Property 101829
Stockbridge house rental
4 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms
  • mountain, resort
  • swimming pool
View Property Details Contact the Owner

Gorgeous brand new lake front property in The Berkshires in Massachusetts

  1. Massachusetts,
  2. Berkshires,
  3. Becket Vacation Home Rentals
— Property 188198
Becket house rental - Front entry
3 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms, 1 Half Bath
  • lake, waterfront
  • air-conditioning
Rates per property (USD)
$150 - $300/night
$1,000 - $1,750/week
$4,000 - $7,000/month
View Property Details Contact the Owner

Secluded Monterey Family Home-Looking for 9 Month renter

  1. Massachusetts,
  2. Berkshires,
  3. Monterey Vacation Home Rentals
— Property 181776
Monterey house rental - Monterrey house in Winter
3 Bedrooms, Sleeps 8
  • House
  • 3 Bathrooms, 1 Half Bath
  • mountain, rural
  • accept credit card
Rates per property (USD)
$2,500 - $3,000/week
$3,000 - $9,000/month
View Property Details Contact the Owner

Charm upon Charm

  1. Massachusetts,
  2. Berkshires,
  3. Richmond Vacation Home Rentals
— Property 190855
Richmond house rental - Front of house- 4 wooded acres behind
4 Bedrooms, Sleeps 8
  • House
  • 4 Bathrooms
  • mountain, rural
  • accept credit card
Rates per property (USD)
$200 - $600/night
$1,500 - $2,500/week
$6,000 - $7,000/month
View Property Details Contact the Owner

Luxurious Contemporary Home Beside Babbling Brook

  1. Massachusetts,
  2. Berkshires,
  3. Becket Vacation Home Rentals
— Property 309155
Becket house rental - Front of House
4 Bedrooms, Sleeps 9
  • House
  • 2 Bathrooms, 1 Half Bath
  • lake, mountain
  • air-conditioning
View Property Details Contact the Owner

The Pastures: an Experience Not to Miss & Limited Availability

  1. Massachusetts,
  2. Berkshires,
  3. New Marlborough Vacation Home Rentals
— Property 186311
New Marlborough estate rental - The Pastures
6 Bedrooms, Sleeps 14
  • Estate
  • 4 Bathrooms, 2 Half Baths
  • mountain, rural
  • accept credit card
View Property Details Contact the Owner

Elegant country living in the heart of the Berkshires, Lenox, MA

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 162997
Lenox house rental - 'The Lenox House'
3 Bedrooms, Sleeps 7
  • House
  • 2 Bathrooms
  • mountain, rural
  • air-conditioning
Rates per property (USD)
$1,300 - $1,600/week
$4,800 - $6,000/month
View Property Details Contact the Owner

The Parsonage. New luxury 4 bedroom 3.5 bath home with in-ground pool

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 146400
Lenox house rental - front of the Parsonage
4 Bedrooms, Sleeps 8
  • House
  • 3 Bathrooms, 1 Half Bath
  • rural, village
  • accept credit card
Rates per property (USD)
$12,000/month
View Property Details Contact the Owner

Luxurious Secluded Hilltop Carriage House

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 100299
Great Barrington house rental - Front view of the House
3 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms
  • mountain, river
  • air-conditioning
Rates per property (USD)
$2,500/week
View Property Details Contact the Owner

Lovely, Executive Home with Numerous Amenities

  1. Massachusetts,
  2. Berkshires,
  3. Williamstown Vacation Home Rentals
— Property 159974
Williamstown house rental
5 Bedrooms, Sleeps 10
  • House
  • 4 Bathrooms
  • river, village
  • air-conditioning
View Property Details Contact the Owner

'Village View'- Spacious, Secluded 1890's Lenox Village Gem

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 156305
Lenox house rental - View of house as you come up the street
5 Bedrooms, Sleeps 10
  • House
  • 3 Bathrooms
  • mountain, village
  • washing machine
Rates per property (USD)
$2,200 - $4,000/week
$7,500 - $13,000/month
View Property Details Contact the Owner

Spa-like, new luxury home in the Berkshires w/fantastic mountain views

  1. Massachusetts,
  2. Berkshires,
  3. South Egremont Vacation Home Rentals
— Property 136689
South Egremont house rental - Mountain Views
4 Bedrooms, Sleeps 10
  • House
  • 3 Bathrooms
  • mountain, rural
  • air-conditioning
Rates per property (USD)
$250 - $400/night
$800 - $1,000/week
$1,950 - $8,000/month
View Property Details Contact the Owner

Comfortable Living in Historic Walk-To-Town Building

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 164150
Great Barrington apartment rental - Quiet spot in town on tree-lined, dead end street
2 Bedrooms, Sleeps 6
  • Apartment
  • 1 Bathroom
  • town
  • accept credit card
View Property Details Contact the Owner

Comfortable living in historic walk-to-town building

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 123274
Great Barrington apartment rental - Quiet location on a dead end street in town
2 Bedrooms, Sleeps 6
  • Apartment
  • 1 Bathroom
  • town
  • accept credit card
Rates per property (USD)
$200 - $250/night
$1,150 - $1,350/week
$1,925 - $2,500/month
View Property Details Contact the Owner

New 4 bedroom luxury Berkshire condo on Ski slope. Ski from back door to slope

  1. Massachusetts,
  2. Berkshires,
  3. Pittsfield Vacation Home Rentals
— Property 175871
Pittsfield condo rental - Front of building. Ski out back door to trail
4 Bedrooms, Sleeps 8
  • Condo
  • 3 Bathrooms, 1 Half Bath
  • mountain
  • air-conditioning
View Property Details Contact the Owner

Private Large Contemporary Victorian / Tangelwood

  1. Massachusetts,
  2. Berkshires,
  3. Stockbridge Vacation Home Rentals
— Property 145364
Stockbridge house rental
3 Bedrooms, Sleeps 8
  • House
  • 3 Bathrooms, 1 Half Bath
  • mountain, rural
  • air-conditioning
Rates per property (USD)
$300/night
$1,700/week
$6,400/month
View Property Details Contact the Owner

New Contemporary Log Home with Boat Dock/Butternut Ski Basin

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 150942
Great Barrington house rental
4 Bedrooms, Sleeps 9
  • House
  • 3 Bathrooms
  • lake, mountain
  • air-conditioning
View Property Details Contact the Owner
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