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Sheffield Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
24 rentals in Sheffield.
Family Friendly in Sheffield, private yet close to everything!, vacation rental in Sheffield
Family Friendly in Sheffield, private yet close to everything!, vacation rental in Sheffield
Family Friendly in Sheffield, private yet close to everything!, vacation rental in Sheffield

Family Friendly in Sheffield, private yet close to everything!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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“Elterwater”—Your own lakefront oasis, a true Berkshire getaway., vacation rental in Sheffield
“Elterwater”—Your own lakefront oasis, a true Berkshire getaway., vacation rental in Sheffield
“Elterwater”—Your own lakefront oasis, a true Berkshire getaway., vacation rental in Sheffield

“Elterwater”—Your own lakefront oasis, a true Berkshire getaway.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Gorgeous Sheffield Home in Heart of Berkshires, vacation rental in Sheffield
Gorgeous Sheffield Home in Heart of Berkshires, vacation rental in Sheffield
Gorgeous Sheffield Home in Heart of Berkshires, vacation rental in Sheffield

Gorgeous Sheffield Home in Heart of Berkshires

Rental Home
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room, vacation rental in Sheffield
12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room, vacation rental in Sheffield
12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room, vacation rental in Sheffield

12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Antique Farmhouse Totally Restored, vacation rental in Sheffield
Antique Farmhouse Totally Restored, vacation rental in Sheffield
Antique Farmhouse Totally Restored, vacation rental in Sheffield

Antique Farmhouse Totally Restored

Rental Home
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Whitney by AvantStay | Private Berkshires Estate, vacation rental in Sheffield
Whitney by AvantStay | Private Berkshires Estate, vacation rental in Sheffield
Whitney by AvantStay | Private Berkshires Estate, vacation rental in Sheffield

Whitney by AvantStay | Private Berkshires Estate

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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August thru Labor Day is still available. Hurry. Berkshires 1 BR. 2 Person Max., vacation rental in Sheffield
August thru Labor Day is still available. Hurry. Berkshires 1 BR. 2 Person Max., vacation rental in Sheffield
August thru Labor Day is still available. Hurry. Berkshires 1 BR. 2 Person Max., vacation rental in Sheffield

August thru Labor Day is still available. Hurry. Berkshires 1 BR. 2 Person Max.

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Winter in the Berkshires- warm and loved 3 bedroom home, vacation rental in Sheffield
Winter in the Berkshires- warm and loved 3 bedroom home, vacation rental in Sheffield
Winter in the Berkshires- warm and loved 3 bedroom home, vacation rental in Sheffield

Winter in the Berkshires- warm and loved 3 bedroom home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Little House in the Woods, vacation rental in Sheffield
Little House in the Woods, vacation rental in Sheffield
Little House in the Woods, vacation rental in Sheffield

Little House in the Woods

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Ashley Falls Getaway, vacation rental in Sheffield
Charming Ashley Falls Getaway, vacation rental in Sheffield
Charming Ashley Falls Getaway, vacation rental in Sheffield

Charming Ashley Falls Getaway

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful Mountainside House with nearby Lake and Hiking Trails, vacation rental in Sheffield
Beautiful Mountainside House with nearby Lake and Hiking Trails, vacation rental in Sheffield
Beautiful Mountainside House with nearby Lake and Hiking Trails, vacation rental in Sheffield

Beautiful Mountainside House with nearby Lake and Hiking Trails

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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COME STAY AT THE SHEFFIELD CHALET!, vacation rental in Sheffield
COME STAY AT THE SHEFFIELD CHALET!, vacation rental in Sheffield
COME STAY AT THE SHEFFIELD CHALET!, vacation rental in Sheffield

COME STAY AT THE SHEFFIELD CHALET!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!, vacation rental in Sheffield
Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!, vacation rental in Sheffield
Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!, vacation rental in Sheffield

Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music, vacation rental in Sheffield
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music, vacation rental in Sheffield
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music, vacation rental in Sheffield

PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Waterfront Sheffield Escape w/ Spacious Yard!, vacation rental in Sheffield
Waterfront Sheffield Escape w/ Spacious Yard!, vacation rental in Sheffield
Waterfront Sheffield Escape w/ Spacious Yard!, vacation rental in Sheffield

Waterfront Sheffield Escape w/ Spacious Yard!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Berkshire County Retreat, vacation rental in Sheffield
Private Berkshire County Retreat, vacation rental in Sheffield
Private Berkshire County Retreat, vacation rental in Sheffield

Private Berkshire County Retreat

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cheerful 3-bedroom cottage with woodstove, vacation rental in Sheffield
Cheerful 3-bedroom cottage with woodstove, vacation rental in Sheffield
Cheerful 3-bedroom cottage with woodstove, vacation rental in Sheffield

Cheerful 3-bedroom cottage with woodstove

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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River Orchard Meadow, vacation rental in Sheffield
River Orchard Meadow, vacation rental in Sheffield
River Orchard Meadow, vacation rental in Sheffield

River Orchard Meadow

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Serene Berkshire Artist's House, vacation rental in Sheffield
Serene Berkshire Artist's House, vacation rental in Sheffield
Serene Berkshire Artist's House, vacation rental in Sheffield

Serene Berkshire Artist's House

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Maplewood: Historic home with pool and hot tub, vacation rental in Sheffield
Maplewood: Historic home with pool and hot tub, vacation rental in Sheffield
Maplewood: Historic home with pool and hot tub, vacation rental in Sheffield

Maplewood: Historic home with pool and hot tub

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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88 acres of Beauty in the Berkshires  - Family Friendly w/ Tennis Court, vacation rental in Sheffield
88 acres of Beauty in the Berkshires  - Family Friendly w/ Tennis Court, vacation rental in Sheffield
88 acres of Beauty in the Berkshires  - Family Friendly w/ Tennis Court, vacation rental in Sheffield

88 acres of Beauty in the Berkshires - Family Friendly w/ Tennis Court

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Historic (updated)1812 Federal brick house well situated in Berkshires with pool, vacation rental in Sheffield
Historic (updated)1812 Federal brick house well situated in Berkshires with pool, vacation rental in Sheffield
Historic (updated)1812 Federal brick house well situated in Berkshires with pool, vacation rental in Sheffield

Historic (updated)1812 Federal brick house well situated in Berkshires with pool

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Private Berkshire County Retreat, vacation rental in Sheffield
Private Berkshire County Retreat, vacation rental in Sheffield
Private Berkshire County Retreat, vacation rental in Sheffield

Private Berkshire County Retreat

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Freeman - Newly Renovated 14K SF Estate on 40 Acres, vacation rental in Sheffield
The Freeman - Newly Renovated 14K SF Estate on 40 Acres, vacation rental in Sheffield
The Freeman - Newly Renovated 14K SF Estate on 40 Acres, vacation rental in Sheffield

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

Rental Home
7 bedrooms
6 bathrooms
Sleeps 30
Match: Sleeps
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