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House Rentals - Sheffield, MA
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50 rentals
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Close To Skiing! Beautiful +Family Friendly - W Tree House & Tennis Court
93 reviews
4 bedrooms
3 bathrooms
Sleeps 9
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Antique Farmhouse Totally Restored
56 reviews
4 bedrooms
3 bathrooms
Sleeps 16
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Spacious Country Retreat With Secluded Tree Top Mountain Views
25 reviews
6 bedrooms
5 bathrooms
Sleeps 12
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Beautiful Mountainside House with nearby Lake and Hiking Trails
11 reviews
3 bedrooms
2 bathrooms
Sleeps 8
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The Little House in the Woods
13 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Newly Renovated Country Retreat-Berkshires
7 reviews
3 bedrooms
3 bathrooms
Sleeps 7
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PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music
8 reviews
3 bedrooms
2 bathrooms
Sleeps 9
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Beautiful Berkshire Home - Enjoy all Summer, Fall & Winter Attractions
5 reviews
3 bedrooms
3 bathrooms
Sleeps 6
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Large Country Home, Sleeps 10! Enjoy the Firepit and Ski Butternut
1 review
5 bedrooms
3 bathrooms
Sleeps 10
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Great Barrington Retreat ! Booking for the Fall & Winter Now!
52 reviews
3 bedrooms
3 bathrooms
Sleeps 7
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Room to Roam. Modern home with all amenities + sep. cabin on 10+ wooded acres.
42 reviews
4 bedrooms
3 bathrooms
Sleeps 8
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Private rustic cottage with lake access
38 reviews
2 bedrooms
1 bathroom
Sleeps 6
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Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
33 reviews
5 bedrooms
3 bathrooms
Sleeps 12
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Beautiful Southfield Village!
20 reviews
3 bedrooms
3 bathrooms
Sleeps 6
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Downtown GB apartment walk to shops and restaurants
23 reviews
2 bedrooms
1 bathroom
Sleeps 5
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North Canaan's Quiet & Cozy Home
38 reviews
3 bedrooms
2 bathrooms
Sleeps 8
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Lake Community - Near Town, Attractions
27 reviews
2 bedrooms
1 bathroom
Sleeps 6
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Stunning Renovated Victorian
16 reviews
5 bedrooms
5 bathrooms
Sleeps 12
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Fall/Winter Mountain Spa Sanctuary with 15 Acre Trail System
16 reviews
2 bedrooms
1 bathroom
Sleeps 6
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A Beautiful Cabin In The Heart Of The Berkshires
14 reviews
3 bedrooms
2 bathrooms
Sleeps 8
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HOT TUB, FIREPLACE, BEAUTIFUL, COMFORTABLE, WALK TO RESTAURANTS, WEEKEND RATES!
12 reviews
5 bedrooms
3 bathrooms
Sleeps 10
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NEW SECLUDED 3 BEDROOM COUNTRY CASTLE
7 reviews
3 bedrooms
3 bathrooms
Sleeps 6
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Berkshires, Ma. Close to Tanglewood, Jacob's PIllow, Berkshire Theater
8 reviews
3 bedrooms
2 bathrooms
Sleeps 8
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Gem of the Berkshires, walk to downtown & lake.
4 reviews
5 bedrooms
4 bathrooms
Sleeps 12
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Waterfront Cottage - 10 Mins to Great Barrington!
4 reviews
2 bedrooms
1 bathroom
Sleeps 2
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CAMP HOUSE on Twin Lakes
4 reviews
6 bedrooms
3 bathrooms
Sleeps 12
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Charming, Private Guest Suite-Historic New Village in the Berkshires
4 reviews
1 bedroom
1 bathroom
Sleeps 2
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Modern Farmhouse in the Southern Berkshires
3 reviews
4 bedrooms
3 bathrooms
Sleeps 8
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Cozy Berkshire home close to Lake Buel, Butternut and Great Barrington.
3 reviews
3 bedrooms
2 bathrooms
Sleeps 6
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Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington
2 reviews
4 bedrooms
4 bathrooms
Sleeps 8
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Modern Victorian on the Hill
2 reviews
4 bedrooms
3 bathrooms
Sleeps 10
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Great Barrington - The Cottage at Windflower Inn - Low Price - Close to Skiing
2 reviews
0 bedrooms
3 bathrooms
Sleeps 9
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Charming 2+2 Lakeside Cottage on Best Lake in CT
1 review
2 bedrooms
2 bathrooms
Sleeps 4
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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
1 review
1 bedroom
1 bathroom
Sleeps 4
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Magnificent views, walk to Lake Mansfield!
1 review
3 bedrooms
3 bathrooms
Sleeps 8
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Charming Ashley Falls Cottage Retreat
1 review
2 bedrooms
2 bathrooms
Sleeps 4
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'The Mill River Cabin’ w/ Fireplace & River View!
1 review
2 bedrooms
1 bathroom
Sleeps 5
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Berkshires- Full First Floor Guest Suite in Historic NE Village
1 review
1 bedroom
1 bathroom
Sleeps 2
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Renovated house on the Hill. Walk everywhere!
1 review
4 bedrooms
3 bathrooms
Sleeps 10
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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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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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NEW! Cozy Great Barrington Home 1 Mi to Ski Resort
4 bedrooms
2 bathrooms
Sleeps 9
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