Berkshires Vacation Rentals

104 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

Charming, Berkshires Ski/Lakehouse....country setting...only 6 miles to Gt Barr.

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 109882
Great Barrington 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 - $2,000/week
$3,000 - $6,000/month
View Property Details Contact the Owner

Jiminy Peak mountainside condo for all seasons

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

New private carriage house in the woods

  1. Massachusetts,
  2. Berkshires,
  3. Becket Vacation Home Rentals
— Property 184864
Becket house rental - front view of carriage house
1 Bedroom, Sleeps 5
  • House
  • 1 Bathroom
  • mountain, rural
  • accept credit card
Rates per property (USD)
$150 - $160/night
$750 - $900/week
View Property Details Contact the Owner

Jem's Berkshire Rental

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home 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

Time for Apple Picking and Leaf Peeping! We're just 7 mins off the Mohawk Trail!

  1. Massachusetts,
  2. Berkshires,
  3. Savoy Vacation Home Rentals
— Property 167483
Savoy cabin rental - Front of cabin in the Berkshires in Autumn
2 Bedrooms, Sleeps 8
  • Cabin
  • 1 Bathroom
  • mountain, river
  • accept credit card
Rates per property (USD)
$125 - $175/night
$900 - $1,000/week
$3,400 - $3,800/month
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

Unique Spacious Hideaway: Conv. Barn on 120 Acres; All Amenities

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Vacation Home Rentals
— Property 167191
Hancock barn rental
4 Bedrooms, Sleeps 11
  • Barn
  • 2 Bathrooms
  • mountain, rural
  • swimming pool
Rates per property (USD)
$3,500/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

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

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

  1. Massachusetts,
  2. Berkshires,
  3. Monterey Vacation Home 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 Vacation Home 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

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

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

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

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

  1. Massachusetts,
  2. Berkshires,
  3. Shelburne Falls Vacation Home 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

Radiant Foliage, Romance, Relaxation, Cozy Log cabin

  1. Massachusetts,
  2. Berkshires,
  3. Becket Vacation Home Rentals
— Property 131221
Becket cabin rental - Welcome to Wisteria Cottage
1 Bedroom, Sleeps 2
  • Cabin
  • 1 Bathroom
  • lake, mountain
  • washing machine
Rates per property (USD)
$130 - $155/night
$725 - $875/week
$2,100 - $2,600/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

Ford Hill Farm

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

Jiminy Peak: The place to **Stay** and **Enjoy**...2/2 in the Berkshires

  1. Berkshires,
  2. Jiminy Peak,
  3. Hancock Vacation Home Rentals
— Property 145038
Hancock townhome rental - Photo merge of living room
2 Bedrooms, Sleeps 6
  • Townhome
  • beach, mountain
  • accept credit card
Rates per property (USD)
$198 - $478/night
$1,244/week
$2,930/month
View Property Details Contact the Owner

Lake Cottage Updated - Town, Attractions nearby

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 118766
Great Barrington cottage rental
2 Bedrooms, Sleeps 6
  • Cottage
  • 1 Bathroom
  • lake, mountain
  • air-conditioning
View Property Details Contact the Owner

Berkshires Country Vacation Home

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 217635
Great Barrington house rental - Backyard patio
3 Bedrooms, Sleeps 6
  • House
  • 1 Bathroom
  • mountain, rural
  • washing machine
View Property Details Contact the Owner

Beautiful, spacious Lenox Colonial with pastoral mountain views

  1. Massachusetts,
  2. Berkshires,
  3. Lenox Vacation Home Rentals
— Property 174219
Lenox house rental - Front of house
4 Bedrooms, Sleeps 10
  • House
  • 4 Bathrooms, 1 Half Bath
  • mountain, rural
  • air-conditioning
Rates per property (USD)
$2,000/week
$8,000/month
View Property Details Contact the Owner

Historic Colonial Replica on 8.5 Wooded Acres

  1. Massachusetts,
  2. Berkshires,
  3. Dalton Vacation Home Rentals
— Property 122527
Dalton house rental - Coming up the Driveway!!
3 Bedrooms, Sleeps 9
  • House
  • 2 Bathrooms, 1 Half Bath
  • mountain, rural
  • swimming pool
Rates per property (USD)
$300/night
$1,900/week
View Property Details Contact the Owner

Norwich Lake Vacation Rental - Cottage- Lake Rights-Use Of Our Private Dock

  1. Massachusetts,
  2. Berkshires,
  3. Huntington Vacation Home Rentals
— Property 183539
Huntington cottage rental - Cottage at Norwich Lake
2 Bedrooms, Sleeps 6
  • Cottage
  • 1 Bathroom
  • lake, mountain
  • washing machine
View Property Details Contact the Owner
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