Holiday Apartments in Sheffield
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28 rentals in Sheffield.
Family Friendly in Sheffield, private yet close to everything!
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“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
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Gorgeous Sheffield Home in Heart of Berkshires
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12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room
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Antique Farmhouse Totally Restored
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Whitney by AvantStay | Private Berkshires Estate
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Little House in the Woods by Evergreen Home
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Charming Ashley Falls Getaway
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Beautiful Mountainside House with nearby Lake and Hiking Trails
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COME STAY AT THE SHEFFIELD CHALET!
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Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!
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PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music
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Skiing & Hiking: Water-View Home in the Berkshires
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Enjoy Winter in the Berkshires at this cozy private getaway
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cheerful 3-bedroom cottage with woodstove
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Beautiful Berkshires Farmhouse with game room and plenty of room
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Serene Berkshire Artist's House
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Ashley Falls Home w/ Fire Pit: Hike & Ski!
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Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly
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Historic (updated)1812 Federal brick house well situated in Berkshires with pool
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The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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The Race Mountain House
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Blue Elm - A Historic Berkshire Cottage
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Remodeled Unit #2, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
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Serene 5-BR Retreat 9-Min to Catamount
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Guesthouse Cabin vacation rentals in Berkshire County
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Showing results 1-28 of 28
Frequently Asked Questions about Sheffield
- Yes, here are some popular holiday rentals in Sheffield that have a pool:
- Family Friendly in Sheffield, private yet close to everything!
- “Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
- Gorgeous Sheffield Home in Heart of Berkshires
- Yes, here are some popular holiday rentals in Sheffield that have internet access:
- Family Friendly in Sheffield, private yet close to everything!
- “Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
- Gorgeous Sheffield Home in Heart of Berkshires
- Some of the most popular kid friendly rentals in Sheffield are:
- Family Friendly in Sheffield, private yet close to everything!
- “Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
- Gorgeous Sheffield Home in Heart of Berkshires
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