Berkshires Vacation Rentals

53 Properties, sort by: 
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Lovely Lenox Colonial with mountain views yet one mile from center of town

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 174313
Lenox house rental - Front of house
4 Bedrooms, Sleeps 9
  • House
  • 2 Bathrooms, 1 Half Bath
  • mountain, rural
  • washing machine
Rates per property (USD)
$250 - $450/night
$2,000 - $3,500/week
$6,500 - $11,000/month
View Property Details Contact the Owner

Berkshires, Lake Buel Waterfront Cottage, COLUMBUS DAY WEEKEND, PRIVACY

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 183642
Great Barrington house rental - Private Cove
2 Bedrooms, Sleeps 6
  • House
  • 1 Bathroom, 1 Half Bath
  • lake, waterfront
  • internet access
Rates per property (USD)
$200/night
View Property Details Contact the Owner

Rustic Home in Exclusive Lakeside Community

  1. Massachusetts,
  2. Berkshires,
  3. Otis Vacation Home Rentals
— Property 178168
Otis house rental
4 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms, 1 Half Bath
  • lake, mountain
  • swimming pool
Rates per property (USD)
$300/night
$1,500 - $2,000/week
$4,000 - $5,000/month
View Property Details Contact the Owner

New England Country Home, 'Frog Hollow'

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 101823
Great Barrington house rental
4 Bedrooms, Sleeps 9
  • House
  • 2 Bathrooms, 1 Half Bath
  • rural
  • air-conditioning
Rates per property (USD)
$250 - $300/night
$850 - $2,100/week
$5,500 - $8,000/month
View Property Details Contact the Owner

Beautiful Bungalow Beside Babbling Brooks

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

Quaint Three Bedroom House in the Berkshire Mountains Five-minute Walk from Will

  1. Massachusetts,
  2. Berkshires,
  3. Williamstown Vacation Home Rentals
— Property 311008
Williamstown house rental
3 Bedrooms, Sleeps 8
  • House
  • 1 Bathroom
  • mountain, village
  • washing machine
View Property Details Contact the Owner

Beautiful New Lindal Cedar Home with Great Lake Views

  1. Massachusetts,
  2. Berkshires,
  3. Hinsdale Vacation Home Rentals
— Property 156700
Hinsdale house rental - Front of House
4 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms, 1 Half Bath
  • lake
  • accept credit card
Rates per property (USD)
$2,000/week
$7,000/month
View Property Details Contact the Owner

Charming Lakefront on Stockbridge Bowl for Fall foliage

  1. Massachusetts,
  2. Berkshires,
  3. Stockbridge Vacation Home Rentals
— Property 132791
Stockbridge house rental - Lake view from back deck
3 Bedrooms, Sleeps 8
  • House
  • lake, rural
  • washing machine
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

Cute Berkshires Cottage

  1. Massachusetts,
  2. Berkshires,
  3. Otis Vacation Home Rentals
— Property 124984
Otis house rental
3 Bedrooms, Sleeps 7
  • House
  • 3 Bathrooms
  • mountain, rural
  • washing machine
Rates per property (USD)
$800/week
$2,350/month
View Property Details Contact the Owner

Berkshires Vacation Home on Hayden Pond

  1. Massachusetts,
  2. Berkshires,
  3. Otis Vacation Home Rentals
— Property 187303
Otis house rental - Charming and Welcoming Farm House
6 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms
  • lake, waterfront
  • washing machine
Rates per property (USD)
$800 - $1,000/week
View Property Details Contact the Owner

Comfortable 5 Bdrm House -Great Get-a-Way!

  1. Massachusetts,
  2. Berkshires,
  3. Lee Vacation Home Rentals
— Property 150566
Lee house rental - Living room with an amazing view
5 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms, 1 Half Bath
  • lake, mountain
  • washing machine
Rates per property (USD)
$36 - $365/night
$2,600/week
$9,000/month
View Property Details Contact the Owner

Whitman Woods: Private Berkshire Vacation, 4 acres

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Vacation Home Rentals
— Property 138408
Hancock house rental - Whitman Woods & House - summer
4 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • mountain, rural
  • washing machine
View Property Details Contact the Owner

Charming Berkshires Lakefront House with Beautiful Views

  1. Massachusetts,
  2. Berkshires,
  3. Cheshire Vacation Home Rentals
— Property 122780
Cheshire house rental - View of house from edge of lake
3 Bedrooms, Sleeps 8
  • House
  • 1 Bathroom
  • lake, mountain
  • air-conditioning
Rates per property (USD)
$175 - $200/night
$850 - $1,150/week
View Property Details Contact the Owner

Mountainside Luxury Retreat in the Berkshires with Breathtaking Views!

  1. Massachusetts,
  2. Berkshires,
  3. Lee Vacation Home Rentals
— Property 173438
Lee house rental - Open kitchen, breakfast room with amazing views!
4 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms, 1 Half Bath
  • mountain, town
  • accept credit card
Rates per property (USD)
$2,000/week
$4,000 - $10,000/month
View Property Details Contact the Owner

Bright New England Cape, Private

  1. Massachusetts,
  2. Berkshires,
  3. Sheffield Vacation Home Rentals
— Property 130359
Sheffield house rental - front view
4 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • mountain, rural
  • air-conditioning
Rates per property (USD)
$1,400/week
View Property Details Contact the Owner

Charming Lenox Home walk to town and close to Tanglewood

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 185249
Lenox house rental - Front Yard
3 Bedrooms, Sleeps 6
  • House
  • 1 Bathroom
  • rural, village
  • air-conditioning
Rates per property (USD)
$200 - $250/night
$1,000 - $1,500/week
$2,800 - $4,200/month
View Property Details Contact the Owner

A Berkshire Jewel with Mountain Vista!

  1. Massachusetts,
  2. Berkshires,
  3. Sheffield Vacation Home Rentals
— Property 184888
Sheffield house rental - Front Yard
4 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • river, rural
  • air-conditioning
Rates per property (USD)
$200 - $250/night
$1,000 - $1,500/week
$3,500 - $4,500/month
View Property Details Contact the Owner

Weekly Rental-Fully furnished/renovated 1 mi. to Jiminy Peak

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Vacation Home Rentals
— Property 145582
Hancock house rental - Fully Furnished Seasonal Rental
3 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms
  • mountain, rural
  • air-conditioning
Rates per property (USD)
$350/night
View Property Details Contact the Owner

Quiet country setting

  1. Massachusetts,
  2. Berkshires,
  3. Cheshire Vacation Home Rentals
— Property 183299
Cheshire house rental - Furnished house in Cheshire, MA
3 Bedrooms, Sleeps 6
  • House
  • 1 Bathroom
  • rural
  • accept credit card
View Property Details Contact the Owner

Private natural paradise, charming and quiet.

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 132455
Great Barrington house rental - View from Street
3 Bedrooms, Sleeps 6
  • House
  • 1 Bathroom
  • downtown, lake
  • air-conditioning
Rates per property (USD)
$975/week
$3,800/month
View Property Details Contact the Owner

Coveted Leisure Lee Home

  1. Massachusetts,
  2. Berkshires,
  3. Lee Vacation Home Rentals
— Property 118501
Lee house rental
4 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms
  • lake, town
  • air-conditioning
View Property Details Contact the Owner

The Coach House - A Berkshire hillside retreat on 2 acres, lovely views

  1. Massachusetts,
  2. Berkshires,
  3. Lee Vacation Home Rentals
— Property 189406
Lee house rental - Coach House in summer
3 Bedrooms, Sleeps 6
  • House
  • 1 Bathroom, 1 Half Bath
  • mountain, village
  • washing machine
Rates per property (USD)
$600 - $1,500/week
$4,800 - $5,600/month
View Property Details Contact the Owner

Beautiful New England Home, Walk to Tanglewood

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 114464
Lenox house rental
4 Bedrooms, Sleeps 8
  • House
  • 1 Bathroom, 1 Half Bath
  • mountain, town
  • air-conditioning
View Property Details Contact the Owner

Luxury Vacation Home in Private Wooded Lake Community -

  1. Massachusetts,
  2. Berkshires,
  3. Tolland Vacation Home Rentals
— Property 125446
Tolland house rental - Private Wooded Home
3 Bedrooms, Sleeps 7
  • House
  • 1 Bathroom, 1 Half Bath
  • beach, lake
  • air-conditioning
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

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

Pristine Family Victorian: a Short Walk to Lake or Town!!

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 179953
Great Barrington house rental - Pristine Victorian
4 Bedrooms, Sleeps 10
  • House
  • 1 Half Bath
  • lake, mountain
  • washing machine
Rates per property (USD)
$2,000 - $2,500/week
$4,500 - $8,500/month
View Property Details Contact the Owner

Hillside Home with beautiful mountain views

  1. Massachusetts,
  2. Berkshires,
  3. South Egremont Vacation Home Rentals
— Property 185013
South Egremont house rental - Front Porch
3 Bedrooms, Sleeps 8
  • House
  • 1 Bathroom
  • mountain, rural
  • air-conditioning
Rates per property (USD)
$700 - $1,500/week
$1,200 - $4,000/month
View Property Details Contact the Owner
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