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Holiday Homes in Sheffield

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47 rentals in Sheffield.
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The perfect Southern Berkshire winter vacation esc
4 bedrooms
2 bathrooms
Sleeps 10
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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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Beautiful Berkshire Home - Enjoy all Summer, Fall & Winter Attractions
3 bedrooms
3 bathrooms
Sleeps 8
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Elterwater--Your beautiful, stress-free lakefront getaway in the Berkshires.
3 bedrooms
2 bathrooms
Sleeps 4
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Designer Loft Style Residence
3 bedrooms
3 bathrooms
Sleeps 6
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1 other traveller has booked this property
Beautiful House, Featured in 'Country Living' Magazine
3 bedrooms
3 bathrooms
Sleeps 6
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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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Brand new Berkshire home-Perfect getaway house for friends and families
3 bedrooms
3 bathrooms
Sleeps 9
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Beautiful Mountainside House with nearby Lake and Hiking Trails
3 bedrooms
2 bathrooms
Sleeps 8
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Newly Renovated Country Retreat-Berkshires
3 bedrooms
3 bathrooms
Sleeps 7
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The Little House in the Woods
2 bedrooms
2 bathrooms
Sleeps 6
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Berkshires: Romantic Cottage with spectacular view
1 bedroom
1 bathroom
Sleeps 3
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17 other travellers have booked this property
Lakefront Berkshires Ski/Summer House, Great Views
4 bedrooms
2 bathrooms
Sleeps 10
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3 other travellers have booked this property
Newly Renovated Lakefront Getaway on Robinson Pond
3 bedrooms
1 bathroom
Sleeps 5
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5 other travellers have booked this property
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
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
Outdoor getaway hunting,fishing,skiing..relaxation
3 bedrooms
2 bathrooms
Sleeps 9
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11 other travellers have booked this property
The Cottage at Great Falls
2 bedrooms
1 bathroom
Sleeps 4
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1 other traveller has booked this property
Cozy Copake Lake Cottage
3 bedrooms
1 bathroom
Sleeps 6
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Shaker Hill
5 bedrooms
4 bathrooms
Sleeps 10
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3 other travellers have booked this property
The Smith Farm Homestead
1 bedroom
1 bathroom
Sleeps 2
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17 other travellers have booked this property
RiverSong Suite In The Berkshires
1 bedroom
1 bathroom
Sleeps 2
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31 other travellers have booked this property
Cozy and clean in Gt Barrington- available for October
2 bedrooms
2 bathrooms
Sleeps 4
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Fabulous Post & Beam Berkshire Rental
0 bedrooms
2 bathrooms
Sleeps 7
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Beautiful Cottage at the foot of the Berkshires
2 bedrooms
1 bathroom
Sleeps 4
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Country Victorian Serenity in the Berkshires
4 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Lakefront Berkshire Rental
5 bedrooms
2 bathrooms
Sleeps 6
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Riverwood - Cozy Carriage House in the Woods
1 bedroom
1 bathroom
Sleeps 2
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2 other travellers have booked this property
Waterfront Cottage - 10 Mins to Great Barrington!
2 bedrooms
1 bathroom
Sleeps 4
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8 other travellers have booked this property
Spacious Lakeside Berkshire Home
4 bedrooms
5 bathrooms
Sleeps 10
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1 other traveller has booked this property
RIVERSONG 'PENTHOUSE'
1 bedroom
1 bathroom
Sleeps 2
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1 other traveller has booked this property
Charming Private Guest Suite in Historic Village in the Berkshires
0 bedrooms
1 bathroom
Sleeps 2
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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
1 bedroom
1 bathroom
Sleeps 2
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1 other traveller has booked this property
Cottage on East Twin Lakes, Internet Access, A/C.
3 bedrooms
2 bathrooms
Sleeps 6
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1 other traveller has booked this property
Private Berkshire Estate w/Pool & Tennis Court
4 bedrooms
4 bathrooms
Sleeps 12
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Picturesque 19th century home on 3 private acres
4 bedrooms
2 bathrooms
Sleeps 7
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Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
4 bedrooms
2 bathrooms
Sleeps 10
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1 other traveller has booked this property
Cozy Monterey Home w/ Porch: Walk to Lake Garfield
3 bedrooms
3 bathrooms
Sleeps 7
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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 - Glacial Erratic at Moore Brook
1 bedroom
1 bathroom
Sleeps 6
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Tentrr Signature - 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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Modern Copake Falls Getaway
1 bedroom
1 bathroom
Sleeps 4
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