Sheffield Vacation Rentals Are Located in Northern Massachusetts

Sheffield vacation rentals are located in the northwest region of Massachusetts, offering you plenty of hiking, skiing, and historical sites. Sheffield cottages are also in the village of Ashley Falls, a small resort town in part of the Pittsfield Metropolitan area. This small town provides a number of Sheffield house rentals, ranging from one bedroom to four bedrooms. Whether you have two or 12 people in your party, you can find the right accommodations in this small town.

Included Amenities at Sheffield Vacation Rentals


Each of the Sheffield vacation rentals will have a full kitchen, allowing you to save money on your trip. You will not have to worry about eating out at local restaurants, unless you want to try some Massachusetts specialties. Local markets are handily located near Sheffield cottages to make it easy for you to get groceries for every meal. A few of the Sheffield house rentals offer tennis courts, riverfront property, views of the mountains, and gardens. You might be able to bring a pet along, depending on your choice of accommodations.

Famous Battle Sites Are Found near Sheffield Cottages


Sheffield cottages were not always in a town named Sheffield. Instead, the town was originally called Outhotonnook. When translated, it means "over the mountain." Of course, the original name was around only during the early 18th century. In 1773, after the Sheffield Resolves, the town was renamed. Even in the early times, there were cottages for the residents. Another bloody battle occurred in Sheffield known as the Shay’s Rebellion. It occurred in 1787 and is considered the bloodiest battle in the area.

Take a Tour of the Ashley House near Your Sheffield House Rentals


During your visit to Sheffield house rentals, consider a tour of Ashley House. It is one of the oldest homes, built in 1753. Colonel John Ashley built the house on Cooper Hill Road for his family. It was the site of the Sheffield Declaration signing which ended British tyranny. The tour takes 45 minutes and picnics are allowed on the grounds. You may consider making a lunch before you leave your Sheffield vacation rentals to take advantage of the Ashley House grounds.

Find more Berkshires vacation rentals and include Great Barrington vacation rentals and Stockbridge rentals in your search.

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Sheffield: Houses, Cottages & More(21)

21 Results
  • 4 BR,
  • 3 BA,
  • Sleeps 15
2 - 5 night minimum stay
(10)
$550 - $571
per night
3 - 31 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 9
3 - 31 night minimum stay
(30)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(12)
$400 - $600
per night
2 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 16
2 - 7 night minimum stay
(25)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(4)
$300
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(17)
$200
per night
5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(5)
$295 - $375
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 night minimum stay
2 Reviews
$400 - $450
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(3)
$2,200 - $2,500
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 12
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 9
2 night minimum stay
$188 - $500
per night
2 - 30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 - 30 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
6 more choices from the HomeAway Network
  • 3 BR,
  • 2 BA,
  • Sleeps 4
2 - 6 night minimum stay
(12)
$275
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(11)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 7 night minimum stay
2 Reviews
$8,500
per month
31 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
31 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
$2,000
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 11
7 night minimum stay
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