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Search over 150,000 vacation rentals properties now! Click here to see more Vacation Homes
Search for vacation rental homes in Berkshires
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Whitman Woods: Private Berkshire Vacation, 4 acres — Property 138408
- House
- 4 bedrooms , sleeps 8
- 2 bathrooms
- mountain, rural
- internet access
- Rates (shown in USD)
- $1000 per property per week
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Apple Valley Log Cabin
Apple Valley Log Cabin - STEAL A HOLIDAY DEAL! — Property 120246
- House
- 3 bedrooms , sleeps 8
- 1 bathroom
- mountain, rural
- jacuzzi
- Rates (shown in USD)
- $1050 per property per week
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Getaway in the Berkshires. Great Barrington has it all. Credit cards accepted — Property 209775
- House
- 5 bedrooms , sleeps 10
- 2 bathrooms
- mountain, town
- internet access
- Rates (shown in USD)
- $1250 - $1800 per property per week
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OverBrook - Privacy & Comfort
OverBrook: Book Now For The Holidays & 2010 — Property 101135
- House
- 3 bedrooms , sleeps 12
- 2 bathrooms
- 1 half bathroom
- lake, village
- garden
- Rates (shown in USD)
- $1400 - $2000 per property per week
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Beautiful Contemporary Home by Stockbridge Bowl — Property 223361
- House
- 3 bedrooms , sleeps 6
- 2 bathrooms
- lake, mountain
- balcony
- Rates (shown in USD)
- $1000 - $2750 per property per week
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Log Cabin in the Northern Berkshires. Modern and Comfortable... — Property 136759
- Cabin
- 1 bedroom , sleeps 3
- 1 bathroom
- mountain, rural
- pets considered
- Rates (shown in USD)
- $760 per property per week
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Monterey Home - Very Private, Outdoor Hot Tub, Close to Lake, Town & Skiiing — Property 227690
- House
- 3 bedrooms , sleeps 8
- 2 bathrooms
- lake, mountain
- garden
- Rates (shown in USD)
- $1100 - $1300 per property per week
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Berkshires 1940's cottage
Lake Buel acess, near Ski Butternut, Tanglewood, child and pet friendly — Property 171589
- Cottage
- 4 bedrooms , sleeps 7
- lake, rural
- pets considered
- Rates (shown in USD)
- $1000 - $1250 per property per week
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Stockbridge Bowl Lake
5 STAR - Berkshire Vacation Home ... Walk to beach — Property 233290
- House
- 4 bedrooms , sleeps 8
- 3 bathrooms
- lake, resort
- terrace
- Rates (shown in USD)
- $2750 - $4000 per property per week
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Charming Lenox Home walk to town and close to Tanglewood — Property 185249
- House
- 3 bedrooms , sleeps 6
- 1 bathroom
- rural, village
- pets considered
- Rates (shown in USD)
- $1500 - $1600 per property per week
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Regions
- Alford rentals (1)
- Ashfield rentals (1)
- Becket rentals (12)
- Charlemont rentals (1)
- Chesterfield rentals (1)
- Dalton rentals (1)
- Great Barrington rentals (38)
- Hinsdale rentals (6)
- Jiminy Peak rentals (18)
- Lee rentals (7)
- Lenox rentals (22)
- Middlefield rentals (3)
- Monterey rentals (6)
- New Marlborough rentals (7)
- North Adams rentals (1)
- Norwich Lake rentals (2)
- Otis rentals (8)
- Pittsfield rentals (5)
- Richmond rentals (2)
- Sandisfield rentals (1)
- Savoy rentals (1)
- Sheffield rentals (9)
- Shelburne Falls rentals (2)
- South Egremont rentals (1)
- Stockbridge rentals (27)
- Tolland rentals (2)
- Tyringham rentals (4)
- West Stockbridge rentals (3)
- Williamstown rentals (9)
Bedrooms
- Studio (3)
- 1 bedroom (12)
- 2 bedrooms (37)
- 3 bedrooms (82)
- 4+ bedrooms (67)
Sleeps
- Sleeps 1-4 (21)
- Sleeps 5-8 (137)
- Sleeps 9-12 (37)
- Sleeps 13 or more (6)
Baths
- 1 bathroom (59)
- 2 bathrooms (94)
- 3 bathrooms (31)
- 4+ bathrooms (11)
Lodging Type
- apartment rentals (6)
- barn rentals (2)
- cabin rentals (9)
- chalet rentals (1)
- condo rentals (13)
- cottage rentals (30)
- estate rentals (9)
- farmhouse rentals (8)
- house rentals (116)
- studio rentals (2)
- townhome rentals (4)
Amenities
- air conditioning (107)
- satellite or cable tv (153)
- pool (38)
- internet access (159)
- dishwasher (166)
- washing machine (170)
Leisure Activities
- Berkshires rentals near fishing (180)
- Berkshires rentals near golf (172)
- Berkshires rentals near skiing (168)
Suitability
- wheelchair accessible (9)
- suitable for elderly or infirm (36)
- pet friendly (82)
- non smoking only (178)

