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Sheffield

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Vacation Rentals in Sheffield, Berkshires

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Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews | Just Added
1-20 of 22
Beautiful Berkshire House Rental with Tennis Court, Sheffield
Massachusetts, Berkshires, Sheffield Holiday Rentals
Beautiful Berkshire House Rental with Tennis Court
Slideshow
4.5 of 5 stars 14 reviews
  • Holiday Rental House
  • 5 Bedrooms, sleeps 9
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Night:
385 AUD - 462 AUD
Week:
2,053 AUD - 2,566 AUD
Month:
4,105 AUD - 8,210 AUD
Minimum rental - 3 nights
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The following rentals are within 25 kilometres of Sheffield, Massachusetts.

Berkshires Cottage 4 bedrooms, sleeps 6, Millerton, NY
United States, New York, Millerton Holiday Rentals
Berkshires Cottage 4 bedrooms, sleeps 6
4 of 5 stars 4 reviews
  • Holiday Rental House
  • 4 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Week:
1,026 AUD
Month:
2,566 AUD
Minimum rental - 2 nights
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Artists' Retreat in Charming Berkshire Village, Mill River
United States, Massachusetts, Mill River Holiday Rentals
Artists' Retreat in Charming Berkshire Village
Slideshow
4 of 5 stars 3 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
257 AUD - 308 AUD
Week:
1,642 AUD - 1,899 AUD
Month:
3,592 AUD - 4,105 AUD
Minimum rental - 2 nights
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3BR Lake house with goregous views, Hillsdale, NY
United States, New York, Hillsdale Holiday Rentals
3BR Lake house with goregous views
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
77 AUD - 180 AUD
Week:
513 AUD - 1,129 AUD
Month:
1,847 AUD - 3,181 AUD
Minimum rental - 1 night
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Berkshires Spacious Comfortable Charming Farmhouse, Lee
Massachusetts, Berkshires, Lee Holiday Rentals
Berkshires Spacious Comfortable Charming Farmhouse
Slideshow
4 of 5 stars 1 review
  • Condo/Apartment
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
308 AUD
Week:
1,232 AUD - 1,539 AUD
Minimum rental - 2 nights
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3 bedroom cottage on quiet road in the Berkshires, Great Barrington
Massachusetts, Berkshires, Great Barrington Holiday Rentals
3 bedroom cottage on quiet road in the Berkshires
4 of 5 stars 4 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 5
  • 1 Bathroom
  • Owner
EMAIL OWNER
Week:
770 AUD - 1,026 AUD
Minimum rental - 1 week
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Bird Watchers Delight! Country Get-Away w/Pond!, Lee
Massachusetts, Berkshires, Lee Holiday Rentals
Bird Watchers Delight! Country Get-Away w/Pond!
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 5 Bedrooms, sleeps 11
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
359 AUD - 385 AUD
Week:
1,539 AUD - 2,463 AUD
Month:
2,976 AUD - 9,134 AUD
Minimum rental - 1 night
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"A Meadow House" Bed and Breakfast or Private Home, Lakeville, CT
United States, Connecticut, Lakeville Holiday Rentals
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 12
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
31 AUD - 308 AUD
Week:
216 AUD - 1,847 AUD
Month:
554 AUD - 5,542 AUD
Minimum rental - 1 night
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The Cottage B&B near Tanglewood in The Berkshires, Stockbridge
Massachusetts, Berkshires, Stockbridge Holiday Rentals
The Cottage B&B near Tanglewood in The Berkshires
Slideshow
4 of 5 stars 9 reviews
  • Guest Room
  • 2 Bedrooms, sleeps 4
  • Verified owner
EMAIL OWNER
Night:
128 AUD - 303 AUD
Week:
1,026 AUD
Month:
2,566 AUD
Minimum rental - 1 night
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Romantic Getaway in an Idyllic Berkshires cottage, Great Barrington
Massachusetts, Berkshires, Great Barrington Holiday Rentals
Romantic Getaway in an Idyllic Berkshires cottage
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 1 Bedroom, sleeps 3
  • 1 Bathroom
  • Owner
EMAIL OWNER
Night:
174 AUD - 200 AUD
Week:
718 AUD - 975 AUD
Minimum rental - 2 nights
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7 Willows Bed & Breakfast, Hillsdale, NY
United States, New York, Hillsdale Holiday Rentals
7 Willows Bed & Breakfast
Slideshow
  • Guest Room
  • 3 Bedrooms, sleeps 10
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
159 AUD
Minimum rental - 2 nights
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Newly Renovated Lakefront Getaway on Robinson Pond, Copake, NY - JUST ADDED
United States, New York, Copake Holiday Rentals
Newly Renovated Lakefront Getaway on Robinson Pond
Slideshow
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
205 AUD - 257 AUD
Week:
1,026 AUD - 1,283 AUD
Month:
4,105 AUD - 4,618 AUD
Minimum rental - 3 nights
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Country Roads Take Me Home, Deeded Lake Access, Copake, NY
United States, New York, Copake Holiday Rentals
Country Roads Take Me Home, Deeded Lake Access
Slideshow
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
1,283 AUD
Minimum rental - 1 night
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Mountain View Inn in Norfolk, CT, Norfolk, CT
United States, Connecticut, Norfolk Holiday Rentals
Mountain View Inn in Norfolk, CT
Slideshow
  • Guest Room
  • 7 Bedrooms, sleeps 16
  • 7 Bathrooms
  • Owner
EMAIL OWNER
Night:
103 AUD - 139 AUD
Minimum rental - 1 night
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Peaceful haven in Great Barrington,Berkshires, Great Barrington - JUST ADDED
Massachusetts, Berkshires, Great Barrington Holiday Rentals
Peaceful haven in Great Barrington,Berkshires
Slideshow
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
144 AUD
Week:
1,001 AUD
Month:
3,900 AUD
Minimum rental - 1 week
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Lovely Cottage Minutes to Tanglewood -Walk to Town, Lee
Massachusetts, Berkshires, Lee Holiday Rentals
Lovely Cottage Minutes to Tanglewood -Walk to Town
Slideshow
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
257 AUD - 308 AUD
Week:
1,232 AUD - 1,539 AUD
Month:
5,644 AUD
Minimum rental - 3 nights
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The Cottage at Devonfield, Lee
Massachusetts, Berkshires, Lee Holiday Rentals
The Cottage at Devonfield
Slideshow
  • Holiday Rental House
  • 1 Bedroom, sleeps 4
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
385 AUD
Week:
2,514 AUD
Month:
9,236 AUD
Minimum rental - 2 nights
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Mountain View Guest House, Norfolk, CT
United States, Connecticut, Norfolk Holiday Rentals
Mountain View Guest House
  • Holiday Rental House
  • 2 Bedrooms, sleeps 4
  • 1 Bathroom
  • Owner
EMAIL OWNER
Night:
334 AUD - 411 AUD
Minimum rental - 1 night
Check availability
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1-20 of 22

Sheffield Holiday Rental Advice

Where else to stay for Tangelwood -besides Lenox?
Posted by needarest67, 30 Apr 2008
... affordable in-town studio or apartment. They are all gone! Well the ones that we could afford are long gone. We are asking for help with finding a PLAN B: Can anyone recommend another town that might be both affordable and within easy driving range of Lenox? A nice hotel ... more
Ideas for girly week in vacation village please
Posted by C from NY, 9 May 2012
... village for a week we enjoyed the area so much that we rented a place in the Berkshires for a summer. After that , we wound up buying a condo and made the move permanent. ;>) I've sent you an overview of the area via the message center. Hope it helps ... more
Monterey vs Otis
Posted by C from NY, 16 Mar 2012
Sounds like you're in for a great vacation. We have a condo in Lenox. Check your messages. I'll be sending you an overview of some stuff to do in the area via message center. ... more
Oak n Spruce - What's the real deal?
Posted by Mel K, 2 Mar 2012
Thank you, C! I stupidly booked the exchange BEFORE I read the reviews thinking I would get a quality condo that I am accustomed to through Diamond. AARRGGHH! I will see if i can cancel the exchange. Thx!!!. ... more
wind in the pines
Posted by tfj, 29 Jun 2011
... is an old converted motel. Condo units have a mini kitchen with small frig, microwave, sink, coffee pot and basic dishes and a window air conditioner. It is clean but definitely OLD. Carpet, draperies, bedding are clean but low-end. Looks like you have stepped back into the 60's ... more
Trip to Berkshires with Young kids in April
Posted by weiler97, 12 Apr 2010
... if you stay in a condo with a kitchen. - Berkshire Museum is a must see. Bottom floor includes a nice aquarium that kept kids enthralled. 2 other floors full of hands-on, intereting but non-pretentious exhibits including a mummy. Traveling exhibit now is 'Armed and Dangrerous' which is basically ... more
Home base in the Berkshires
Posted by dancingnancy, 30 Aug 2009
... and is a ski resort condo-type place. Stockbridge or Lenox are both charming. Stockbridge has the advantage of being 8 miles north of Great Barrington, a really great town that, sadly, doesn't have much in the way of inns or hotels. If you prefer a B&B, Lenox ... more
Berkshires in Massachusetts
Posted by BIGREDDON, 26 Oct 2007
... Brodie Mountain Rd Hancock, Massachusetts 01237 United States My wife and I have stayed here 4 times at different times of the year. We enjoy ourselves with swimming, hiking, eating out, grilling by nearby our condo, visiting various attractions. We are going to be there Oct 27 for a week ... more
Places to stay near Tanglewood
Posted by travelinmidatlantic, 21 May 2007
We are looking for a place to stay in July that would put us near Tanglewood (Lennox) as well as near hiking, fishing, golfing. We would prefer a one bedroom "condo experience" rather than a hotel room. Any recommendations? Thank you. ... more
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