Berkshires Vacation Rentals

29 Properties, sort by: 
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Nestled in a valley of mountains and close to Lenox, Tanglewood Skiing

  1. Massachusetts,
  2. Berkshires,
  3. Dalton Vacation Home Rentals
— Property 145825
Dalton house rental - Open floor plan main level
5 Bedrooms, Sleeps 12
  • House
  • 3 Bathrooms
  • lake, mountain
  • swimming pool
Rates per property (USD)
$350 - $550/night
$1,800/week
$4,500 - $7,000/month
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

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

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

Wonderful Lake House in Berkshires

  1. Massachusetts,
  2. Berkshires,
  3. Becket Vacation Home Rentals
— Property 200507
Becket cabin rental - Front View of House
4 Bedrooms, Sleeps 8
  • Cabin
  • 3 Bathrooms
  • lake, mountain
  • accept credit card
Rates per property (USD)
$175 - $300/night
$1,000 - $1,400/week
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

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

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

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

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

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

Quaint and Quiet Cottage with Lake Rights and Private Dock

  1. Massachusetts,
  2. Berkshires,
  3. Norwich Lake Vacation Home Rentals
— Property 159704
Norwich Lake cottage rental - The Cottage
2 Bedrooms, Sleeps 6
  • Cottage
  • 1 Bathroom
  • lake, mountain
  • pets considered
Rates per property (USD)
$135/night
$750/week
$2,500/month
View Property Details Contact the Owner

Stockbridge: Architect's Home, Walk to Tanglewood

  1. Massachusetts,
  2. Berkshires,
  3. Stockbridge Vacation Home Rentals
— Property 124747
Stockbridge house rental
4 Bedrooms, Sleeps 11
  • House
  • 2 Bathrooms, 1 Half Bath
  • lake, mountain
  • air-conditioning
View Property Details Contact the Owner

Beautiful Lenox Farmhouse with Hot Tub, Pond & Waterfall

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

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

Secluded Tranquility overlooking Hayes Pond in Otis!

  1. Massachusetts,
  2. Berkshires,
  3. Otis Vacation Home Rentals
— Property 187129
Otis house rental - the hammock on the deck in June
4 Bedrooms, Sleeps 10
  • House
  • 3 Bathrooms, 1 Half Bath
  • lake, mountain
  • washing machine
Rates per property (USD)
$1,600 - $2,000/week
$3,500 - $7,000/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

Deluxe New Home, 2 Master Suites, Tanglewood Area

  1. Massachusetts,
  2. Berkshires,
  3. Lee Vacation Home Rentals
— Property 101830
Lee house rental - Front View of 100 Wood Duck Road
6 Bedrooms, Sleeps 12
  • House
  • 2 Bathrooms, 2 Half Baths
  • lake, mountain
  • air-conditioning
Rates per property (USD)
$15,000/month
View Property Details Contact the Owner

Four Season Berkshires Vacation Home

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

Colesbrook Manor Berkshire Cottage

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

Enjoy Lake Buel and Ski Butternut while staying in our new 2 bedroom home

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 148393
Great Barrington house rental - Our New House
2 Bedrooms, Sleeps 6
  • House
  • 1 Bathroom
  • lake, mountain
  • air-conditioning
Rates per property (USD)
$225 - $250/night
$975/week
View Property Details Contact the Owner

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

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

Five Bedroom /Four Season Relaxing House

  1. Massachusetts,
  2. Berkshires,
  3. Lee Vacation Home Rentals
— Property 125683
Lee house rental
7 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms
  • lake, mountain
  • washing machine
Rates per property (USD)
$400/night
$2,500/week
$8,500/month
View Property Details Contact the Owner

Cozy cottage in lake community

  1. Massachusetts,
  2. Berkshires,
  3. Becket Vacation Home Rentals
— Property 161494
Becket cottage rental - The lake which is a 2 minute walk to the beach
2 Bedrooms, Sleeps 3
  • Cottage
  • 1 Bathroom
  • lake, mountain
  • pets considered
Rates per property (USD)
$125/night
$875/week
View Property Details Contact the Owner

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

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

Berkshires Lakefront, Terrific Vacation Delight, We offer our 2nd home to you.

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 184622
Great Barrington house rental
2 Bedrooms, Sleeps 6
  • House
  • 1 Bathroom, 1 Half Bath
  • lake, mountain
  • washing machine
Rates per property (USD)
$1,550/week
View Property Details Contact the Owner

Beautiful Lakefront Berkshires Ski or Summer House

  1. Massachusetts,
  2. Berkshires,
  3. Great Barrington Vacation Home Rentals
— Property 102843
Great Barrington house rental
4 Bedrooms, Sleeps 10
  • House
  • 2 Bathrooms
  • lake, mountain
  • accept credit card
View Property Details Contact the Owner

berkshire farmhouse in comfortable country setting

  1. Massachusetts,
  2. Berkshires,
  3. Pittsfield Vacation Home Rentals
— Property 137293
Pittsfield house rental
3 Bedrooms, Sleeps 11
  • House
  • 2 Bathrooms
  • lake, mountain
  • washing machine
Rates per property (USD)
$250 - $400/night
$1,200 - $2,500/week
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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