Massachusetts Vacation Rentals

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

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock 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

Jiminy Peak mountainside condo for all seasons

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Rentals
— Property 117964
Hancock condo rental
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • mountain, resort
  • swimming pool
View Property Details Contact the Owner

Log Home Nestled in the Woods

  1. Massachusetts,
  2. Berkshires,
  3. Monterey Rentals
— Property 162300
Monterey chalet rental - Summer at the Chalet
3 Bedrooms, Sleeps 7
  • Chalet
  • 2 Bathrooms
  • mountain, rural
  • air-conditioning
Rates per property (USD)
$1,650/week
View Property Details Contact the Owner

Jem's Berkshire Rental

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Rentals
— Property 152703
Great Barrington house rental - House view
3 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms, 1 Half Bath
  • mountain, town
  • accept credit card
Rates per property (USD)
$500/night
$2,800/week
$9,000/month
View Property Details Contact the Owner

Beautiful Bungalow Beside Babbling Brooks

  1. Massachusetts,
  2. Berkshires,
  3. Becket 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

Charming Lakeview Home in Berkshires --- Perfect for fall getaway

  1. Massachusetts,
  2. Berkshires,
  3. Monterey Rentals
— Property 137922
Monterey 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
$1,650/week
$1,150 - $6,600/month
View Property Details Contact the Owner

Family Farmhouse Tudor with 6 Acres

  1. Massachusetts,
  2. Berkshires,
  3. Pittsfield Rentals
— Property 179777
Pittsfield 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
View Property Details Contact the Owner

Whitman Woods: Private Berkshire Vacation, 4 acres

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock 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
SPECIAL OFFER! $350 Discount For Week's Stay October 18 - November 22

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

  1. Massachusetts,
  2. Berkshires,
  3. Shelburne Falls Rentals
— Property 190201
Shelburne Falls cottage rental - Stone facade at cottage entrance
3 Bedrooms, Sleeps 7
  • Cottage
  • 2 Bathrooms
  • mountain, town
  • washing machine
Rates per property (USD)
$980/week
View Property Details Contact the Owner

Bright New England Cape, Private

  1. Massachusetts,
  2. Berkshires,
  3. Sheffield 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

Ford Hill Farm

  1. Massachusetts,
  2. Berkshires,
  3. Sheffield Rentals
— Property 318832
Sheffield farmhouse rental - House
2 Bedrooms, Sleeps 6
  • Farmhouse
  • 2 Bathrooms
  • mountain, rural
  • air-conditioning
View Property Details Contact the Owner

Northampton Vacation Rental-- 3 Bedroom Home with Hot Tub and Tree House

  1. Massachusetts,
  2. Central Massachusetts,
  3. Haydenville Rentals
— Property 183556
Haydenville house rental - Living Area
3 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms
  • mountain, town
  • internet access
Rates per property (USD)
$175/night
$1,000/week
$3,500/month
View Property Details Contact the Owner

Jiminy Peak 4-Level Deluxe Condo - ski resort.- one mile off the mountain!

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Rentals
— Property 101805
Hancock 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
View Property Details Contact the Owner

Sunny Contemporary, Views, Private, near Events

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Rentals
— Property 116237
Great Barrington house rental - view from parking area
3 Bedrooms, Sleeps 7
  • House
  • 2 Bathrooms
  • mountain, rural
  • washing machine
View Property Details Contact the Owner

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

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

Bentley Brook Mountain Club at Jiminy Peak

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Rentals
— Property 136078
Hancock condo rental - Bentley Brook Main Building
2 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • mountain, resort
  • accept credit card
Rates per property (USD)
$200 - $313/night
$1,100 - $2,100/week
View Property Details Contact the Owner

Beautiful Lenox Farmhouse with Hot Tub, Pond & Waterfall

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Rentals
— Property 185184
Lenox farmhouse rental - Front of Farmhouse
4 Bedrooms, Sleeps 8
  • Farmhouse
  • 2 Bathrooms, 1 Half Bath
  • lake, mountain
  • washing machine
Rates per property (USD)
$1,100/week
$4,000/month
View Property Details Contact the Owner

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

  1. Massachusetts,
  2. Berkshires,
  3. Lenox 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

Four Season Berkshires Vacation Home

  1. Massachusetts,
  2. Berkshires,
  3. Otis Rentals
— Property 112829
Otis house rental - The cabin in the Spring
3 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • lake, mountain
  • swimming pool
View Property Details Contact the Owner

Beautiful Berkshire Country House, Views & More

  1. Massachusetts,
  2. Berkshires,
  3. Sheffield Rentals
— Property 104868
Sheffield house rental
3 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms, 1 Half Bath
  • mountain
  • air-conditioning
View Property Details Contact the Owner

Breathtaking Berkshire Rental -

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Rentals
— Property 105168
Hancock condo rental
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • mountain, rural
  • swimming pool
View Property Details Contact the Owner

Luxury Condo with Jacuzzi at Jiminy Peak

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Rentals
— Property 123292
Hancock condo rental
2 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • mountain, resort
  • swimming pool
View Property Details Contact the Owner

Colesbrook Manor Berkshire Cottage

  1. Massachusetts,
  2. Berkshires,
  3. Becket Rentals
— Property 101832
Becket estate rental
3 Bedrooms, Sleeps 8
  • Estate
  • 2 Bathrooms
  • lake, mountain
  • washing machine
View Property Details Contact the Owner

A house for all seasons in the Berkshires

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Rentals
— Property 152718
Lenox house rental
3 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms
  • mountain, village
  • washing machine
Rates per property (USD)
$1,250/month
View Property Details Contact the Owner

Charming House w/ Dock on Lake Garfield FALL WKDS AVAIL NOW!

  1. Massachusetts,
  2. Berkshires,
  3. Monterey Rentals
— Property 123410
Monterey house rental - Front of house facing yard & lake
5 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • lake, mountain
  • air-conditioning
View Property Details Contact the Owner

Classic Modern home, light & bright.

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Rentals
— Property 115280
Lenox house rental - Front view of house
3 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms
  • mountain, town
  • air-conditioning
Rates per property (USD)
$1,200/week
View Property Details Contact the Owner

Beautiful Berkshire Condo

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Rentals
— Property 203915
Lenox condo rental
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • mountain, town
  • tennis
View Property Details Contact the Owner

Pristine Mountain & Water view, Four Season Cottage, Recently Renovated

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Rentals
— Property 146827
Great Barrington cottage rental
2 Bedrooms, Sleeps 6
  • Cottage
  • 2 Bathrooms
  • lake, mountain
  • accept credit card
Rates per property (USD)
$165 - $225/night
$850 - $1,100/week
$2,950 - $3,300/month
View Property Details Contact the Owner

Lovely modern 2 bdrm. in Lenox near Tanglewood, Town Center & Lake

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Rentals
— Property 200829
Lenox house rental - House and deck from backyard
2 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms
  • mountain, village
  • air-conditioning
View Property Details Contact the Owner

Discounted Tanglewood Area Condo with View----

  1. Massachusetts,
  2. Berkshires,
  3. Lee Rentals
— Property 122282
Lee condo rental - View from Condo
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • mountain, resort
  • swimming pool
View Property Details Contact the Owner
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