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Sheffield Vacation Rentals

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50 rentals in Sheffield.
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Close To Skiing! Beautiful +Family Friendly - W Tree House & Tennis Court
4 bedrooms
3 bathrooms
Sleeps 9
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Elterwater--Your beautiful, stress-free lakefront getaway in the Berkshires.
3 bedrooms
2 bathrooms
Sleeps 4
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Antique Farmhouse Totally Restored
4 bedrooms
3 bathrooms
Sleeps 16
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Spacious Country Retreat With Secluded Tree Top Mountain Views
6 bedrooms
5 bathrooms
Sleeps 12
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Beautiful Mountainside House with nearby Lake and Hiking Trails
3 bedrooms
2 bathrooms
Sleeps 8
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The Little House in the Woods
2 bedrooms
2 bathrooms
Sleeps 6
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Newly Renovated Country Retreat-Berkshires
3 bedrooms
3 bathrooms
Sleeps 7
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Beautiful Berkshire Home - Enjoy all Summer, Fall & Winter Attractions
3 bedrooms
3 bathrooms
Sleeps 6
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PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music
3 bedrooms
2 bathrooms
Sleeps 9
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Large Country Home, Sleeps 10! Enjoy the Firepit and Ski Butternut
5 bedrooms
3 bathrooms
Sleeps 10
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Room to Roam. Modern home with all amenities + sep. cabin on 10+ wooded acres.
4 bedrooms
3 bathrooms
Sleeps 8
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Private rustic cottage with lake access
2 bedrooms
1 bathroom
Sleeps 6
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Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
5 bedrooms
3 bathrooms
Sleeps 12
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Beautiful Southfield Village!
3 bedrooms
3 bathrooms
Sleeps 6
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North Canaan's Quiet & Cozy Home
3 bedrooms
2 bathrooms
Sleeps 8
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Stunning Renovated Victorian
5 bedrooms
5 bathrooms
Sleeps 12
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Downtown GB apartment walk to shops and restaurants
2 bedrooms
1 bathroom
Sleeps 5
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Lake Community - Near Town, Attractions
2 bedrooms
1 bathroom
Sleeps 6
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Fall/Winter Mountain Spa Sanctuary with 15 Acre Trail System
2 bedrooms
1 bathroom
Sleeps 6
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HOT TUB, FIREPLACE, BEAUTIFUL, COMFORTABLE, WALK TO RESTAURANTS, WEEKEND RATES!
5 bedrooms
3 bathrooms
Sleeps 10
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A Beautiful Cabin In The Heart Of The Berkshires
3 bedrooms
2 bathrooms
Sleeps 8
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Berkshires, Ma. Close to Tanglewood, Jacob's PIllow, Berkshire Theater
3 bedrooms
2 bathrooms
Sleeps 8
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Gem of the Berkshires, walk to downtown & lake.
5 bedrooms
4 bathrooms
Sleeps 12
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1 other traveller has booked this property
Waterfront Cottage - 10 Mins to Great Barrington!
2 bedrooms
1 bathroom
Sleeps 4
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7 other travellers have booked this property
CAMP HOUSE on Twin Lakes
6 bedrooms
3 bathrooms
Sleeps 12
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Charming, Private Guest Suite-Historic New Village in the Berkshires
1 bedroom
1 bathroom
Sleeps 2
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Modern Farmhouse in the Southern Berkshires
4 bedrooms
3 bathrooms
Sleeps 8
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Open Field House with a View! Dog friendly
3 bedrooms
2 bathrooms
Sleeps 5
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Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington
4 bedrooms
4 bathrooms
Sleeps 8
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Modern Victorian on the Hill
4 bedrooms
3 bathrooms
Sleeps 10
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Great Barrington - The Cottage at Windflower Inn - Low Price - Close to Skiing
0 bedrooms
3 bathrooms
Sleeps 9
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Charming 2+2 Lakeside Cottage on Best Lake in CT
2 bedrooms
2 bathrooms
Sleeps 4
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1 other traveller has booked this property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
1 bedroom
1 bathroom
Sleeps 4
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1 other traveller has booked this property
NEW SECLUDED 3 BEDROOM COUNTRY CASTLE
3 bedrooms
3 bathrooms
Sleeps 6
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Magnificent views, walk to Lake Mansfield!
3 bedrooms
3 bathrooms
Sleeps 8
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Charming Ashley Falls Cottage Retreat
2 bedrooms
2 bathrooms
Sleeps 4
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Berkshires- Full First Floor Guest Suite in Historic NE Village
1 bedroom
1 bathroom
Sleeps 2
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Fabulous Post & Beam Berkshire Rental
0 bedrooms
2 bathrooms
Sleeps 7
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Private Berkshire Estate w/Pool & Tennis Court
4 bedrooms
4 bathrooms
Sleeps 12
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Pet-Friendly Berkshires Home w/Dock & Fire Pit!
3 bedrooms
3 bathrooms
Sleeps 10
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Private Home Overlooking Stevens Lake
3 bedrooms
2 bathrooms
Sleeps 6
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NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr
4 bedrooms
4 bathrooms
Sleeps 8
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Turning Point - Family Retreat & Group Getaway
7 bedrooms
8 bathrooms
Sleeps 15
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Tentrr Signature Site - Echo Hill
1 bedroom
1 bathroom
Sleeps 8
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'The Mill River Cabin’ w/ Fireplace & River View!
2 bedrooms
1 bathroom
Sleeps 5
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Converted Berkshire schoolhouse on a quiet river
3 bedrooms
2 bathrooms
Sleeps 5
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Konkapot Cottage, Pastoral Bliss With Wide Views
3 bedrooms
2 bathrooms
Sleeps 6
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Fantastic Location - Walk to Great Barrington & Lake Mansfield
3 bedrooms
2 bathrooms
Sleeps 4
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Cozy Berkshire home close to Lake Buel, Butternut and Great Barrington.
3 bedrooms
2 bathrooms
Sleeps 6
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