Berkshires Vacation Rentals

27 Properties, sort by:  Availability Last Updated Bedrooms: Least to Most Bedrooms: Most to Least Price: High to Low Price: Low to High Special Offers First

Refine Your Search Start a New Search

Find by availability dates:

Check-in:

Check-out:

Current Criteria:

• Berkshires

  remove

• 2 bathrooms

  remove

• house

  remove

• pet friendly

  remove

(remove all criteria)

• Vacation Spots
  • Great Barrington rentals (5)
  • Hinsdale rentals (2)
  • Lee rentals (1)
  • Lenox rentals (4)
  • Monterey rentals (1)
  • New Marlborough rentals (1)
  • North Egremont rentals (2)
  • Otis rentals (3)
  • Sheffield rentals (3)
  • Stockbridge rentals (5)

• Bedrooms
  • 2 bedrooms (3)
  • 3 bedrooms (12)
  • 4+ bedrooms (12)

• Sleeps
  • Sleeps 5-8 (18)
  • Sleeps 9-12 (9)

• Accessibility
  • long term renters welcome (9)
  • non smoking only (23)
  • wheelchair accessible (3)

• Location Type
  • beach rentals (2)
  • lake rentals (8)
  • mountain rentals (8)
  • river rentals (3)
  • waterfront rentals (4)

• Travel Style
  • luxury rentals (2)

Go to page (Page 1 of 1) 1

Show 15 30 60 rentals per page

Berkshires Vacation Home on Hayden Pond

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

— Property 187303

6 Bedrooms, Sleeps 10

• House
• 2 Bathrooms
• lake, waterfront
• washing machine

Read   Reviews

Write a
Review

Rates per property (USD)

$800 - $1,000/week

View Property Details Contact the Owner

Ski the Berkshires from House on Lake Garfield Monterey

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

— Property 170562

4 Bedrooms, Sleeps 8

• House
• 2 Bathrooms
• town, waterfront
• internet access

Read   Reviews

Write a
Review

Rates per property (USD)

$1,600/month

View Property Details Contact the Owner

Rustic Home in Exclusive Lakeside Community

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

— Property 178168

4 Bedrooms, Sleeps 10

• House
• 2 Bathrooms, 1 Half Bath
• lake, mountain
• swimming pool

Read   Reviews

Write a
Review

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

4 Bedrooms, Sleeps 9

• House
• 2 Bathrooms, 1 Half Bath
• rural
• air-conditioning

Read   Reviews

Write a
Review

Rates per property (USD)

$250 - $300/night

$850 - $2,100/week

$5,500 - $8,000/month

View Property Details Contact the Owner

Quiet Lake house with beautiful water views

1. Massachusetts,
2. Berkshires,
3. Hinsdale Vacation Home Rentals

— Property 190256

2 Bedrooms, Sleeps 8

• House
• 2 Bathrooms
• lake, waterfront
• washing machine

Read   Reviews

Write a
Review

Rates per property (USD)

$140/night

$800 - $1,200/week

View Property Details Contact the Owner

Private Setting in Lenox

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

— Property 207123

3 Bedrooms, Sleeps 6

• House
• 2 Bathrooms
• resort, village
• air-conditioning

Read   Reviews

Write a
Review

Rates per property (USD)

$1,400 - $2,000/week

$2,500 - $7,000/month

View Property Details Contact the Owner

OverBrook - Great local Ski conditions! - packed powder & great base

1. Massachusetts,
2. Berkshires,
3. Stockbridge Vacation Home Rentals

— Property 101135

3 Bedrooms, Sleeps 12

• House
• 2 Bathrooms, 1 Half Bath
• lake, town
• air-conditioning

Read   Reviews

Write a
Review

View Property Details Contact the Owner

A Berkshire Jewel with Mountain Vista!

1. Massachusetts,
2. Berkshires,
3. Sheffield Vacation Home Rentals

— Property 184888

4 Bedrooms, Sleeps 8

• House
• 2 Bathrooms
• river, rural
• air-conditioning

Read   Reviews

Write a
Review

Rates per property (USD)

$200 - $250/night

$1,000 - $1,500/week

$3,500 - $4,500/month

View Property Details Contact the Owner

Historic Colonial by Gardens / Tanglewood

1. Massachusetts,
2. Berkshires,
3. Stockbridge Vacation Home Rentals

— Property 104441

3 Bedrooms, Sleeps 6

• House
• 2 Bathrooms
• air-conditioning
• washing machine

Read   Reviews

Write a
Review

Rates per property (USD)

$8,000/month

View Property Details Contact the Owner

Lakefront Home in Berkshires (Fall Time Periods Available)

1. Massachusetts,
2. Berkshires,
3. Hinsdale Vacation Home Rentals

— Property 118052

4 Bedrooms, Sleeps 8

• House
• 2 Bathrooms
• lake, waterfront
• washing machine

Read   Reviews

Write a
Review

Rates per property (USD)

$1,000 - $1,925/week

View Property Details Contact the Owner

Right Between Tanglewood and Town!

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

— Property 195051

4 Bedrooms, Sleeps 9

• House
• 2 Bathrooms
• accept credit card
• air-conditioning

Read   Reviews

Write a
Review

View Property Details Contact the Owner

Sunny Contemporary, Views, Private, near Events

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

— Property 116237

3 Bedrooms, Sleeps 7

• House
• 2 Bathrooms
• mountain, rural
• washing machine

Read   Reviews

Write a
Review

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

4 Bedrooms, Sleeps 6

• House
• 2 Bathrooms
• mountain, resort
• swimming pool

Read   Reviews

Write a
Review

View Property Details Contact the Owner

Live in an elegant converted church- Book now for Summer 2008!

1. Massachusetts,
2. Berkshires,
3. North Egremont Vacation Home Rentals

— Property 166259

4 Bedrooms, Sleeps 10

• House
• 2 Bathrooms, 1 Half Bath
• mountain, town
• accept credit card

Read   Reviews

Write a
Review

Rates per property (USD)

$1,800 - $2,000/week

$4,000 - $7,000/month

View Property Details Contact the Owner

Luxurious Secluded Hilltop Carriage House

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

— Property 100299

3 Bedrooms, Sleeps 10

• House
• 2 Bathrooms
• mountain, river
• air-conditioning

Read   Reviews

Write a
Review

Rates per property (USD)

$2,500/week

View Property Details Contact the Owner

A Home to go on Vacation To! Tanglewood Music Center, Theater, Antique

1. Massachusetts,
2. Berkshires,
3. North Egremont Vacation Home Rentals

— Property 119062

2 Bedrooms, Sleeps 7

• House
• 2 Bathrooms
• rural
• air-conditioning

Read   Reviews

Write a
Review

View Property Details Contact the Owner

Berkshires lake house near Tanglewood

1. Massachusetts,
2. Berkshires,
3. Lee Vacation Home Rentals

— Property 115113

3 Bedrooms, Sleeps 8

• House
• 2 Bathrooms
• beach, lake
• air-conditioning

Read   Reviews

Write a
Review

Rates per property (USD)

$1,400/week

$6,000/month

View Property Details Contact the Owner

Beautiful Berkshire Country House, Views & More

1. Massachusetts,
2. Berkshires,
3. Sheffield Vacation Home Rentals

— Property 104868

3 Bedrooms, Sleeps 8

• House
• 2 Bathrooms, 1 Half Bath
• mountain
• air-conditioning

Read   Reviews

Write a
Review

View Property Details Contact the Owner

WoodsWhole

1. Massachusetts,
2. Berkshires,
3. Stockbridge Vacation Home Rentals

— Property 216511

3 Bedrooms, Sleeps 6

• House
• 2 Bathrooms, 1 Half Bath
• beach, river
• swimming pool

Read   Reviews

Write a
Review

View Property Details Contact the Owner

Classic Modern home, light & bright.

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

— Property 115280

3 Bedrooms, Sleeps 6

• House
• 2 Bathrooms
• mountain, town
• air-conditioning

Read   Reviews

Write a
Review

Rates per property (USD)

$1,200/week

View Property Details Contact the Owner

Maya's Garden House

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

— Property 151967

3 Bedrooms, Sleeps 8

• House
• 2 Bathrooms
• rural, town
• washing machine

Read   Reviews

Write a
Review

Rates per property (USD)

$1,000/week

$2,500 - $3,000/month

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

4 Bedrooms, Sleeps 10

• House
• 2 Bathrooms
• lake, mountain
• accept credit card

Read   Reviews

Write a
Review

View Property Details Contact the Owner

Lakefront Home with View

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

— Property 101842

6 Bedrooms, Sleeps 11

• House
• 2 Bathrooms
• washing machine
• pets considered

Read   Reviews

Write a
Review

View Property Details Contact the Owner

Antique Farmhouse abutting Conservation Land

1. Massachusetts,
2. Berkshires,
3. New Marlborough Vacation Home Rentals

— Property 108370

4 Bedrooms, Sleeps 8

• House
• 2 Bathrooms
• rural, village
• washing machine

Read   Reviews

Write a
Review

View Property Details Contact the Owner

Fantastic views of Bartholemews Cobble from Brand New Home on 12 Acres

1. Massachusetts,
2. Berkshires,
3. Sheffield Vacation Home Rentals

— Property 124299

2 Bedrooms, Sleeps 8

• House
• 2 Bathrooms
• rural
• washing machine

Read   Reviews

Write a
Review

View Property Details Contact the Owner

Beautiful Stockbridge Contempt, on 16 wooded acres, Pool and Gardens

1. Massachusetts,
2. Berkshires,
3. Stockbridge Vacation Home Rentals

— Property 137118

3 Bedrooms, Sleeps 8

• House
• 2 Bathrooms, 1 Half Bath
• lake, village
• swimming pool

Read   Reviews

Write a
Review

View Property Details Contact the Owner

Tanglewood Area Home in Private Bishop Estates

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

— Property 101847

3 Bedrooms, Sleeps 8

• House
• 2 Bathrooms, 1 Half Bath
• air-conditioning
• washing machine

Read   Reviews

Write a
Review

View Property Details Contact the Owner

Go to page (Page 1 of 1) 1

Show 15 30 60 rentals per page

 

Use of this Web site constitutes acceptance of the HomeAway.com Terms and Conditions and Privacy Policy.

© Copyright 2006-Present HomeAway.com, Inc. All rights reserved.