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Sheffield Holiday Apartments

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Bedrooms

Bathrooms

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5 km
25 rentals in Sheffield.
Family Friendly in Sheffield, private yet close to everything!, holiday rental in Sheffield
Family Friendly in Sheffield, private yet close to everything!, holiday rental in Sheffield
Family Friendly in Sheffield, private yet close to everything!, holiday rental in Sheffield

Family Friendly in Sheffield, private yet close to everything!

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

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

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

Gorgeous Sheffield Home in Heart of Berkshires

Holiday Rental House
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, holiday rental in Sheffield
12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room, holiday rental in Sheffield
12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room, holiday rental in Sheffield

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Antique Farmhouse Totally Restored, holiday rental in Sheffield
Antique Farmhouse Totally Restored, holiday rental in Sheffield
Antique Farmhouse Totally Restored, holiday rental in Sheffield

Antique Farmhouse Totally Restored

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

Whitney by AvantStay | Private Berkshires Estate

Holiday Rental House
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., holiday rental in Sheffield
August thru Labor Day is still available. Hurry. Berkshires 1 BR. 2 Person Max., holiday rental in Sheffield
August thru Labor Day is still available. Hurry. Berkshires 1 BR. 2 Person Max., holiday rental in Sheffield

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Make your getaway to the Berkshires! Convenient to skiing, races, music & dance!, holiday rental in Sheffield
Make your getaway to the Berkshires! Convenient to skiing, races, music & dance!, holiday rental in Sheffield
Make your getaway to the Berkshires! Convenient to skiing, races, music & dance!, holiday rental in Sheffield

Make your getaway to the Berkshires! Convenient to skiing, races, music & dance!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Winter in the Berkshires- warm and loved 3 bedroom home, holiday rental in Sheffield
Winter in the Berkshires- warm and loved 3 bedroom home, holiday rental in Sheffield
Winter in the Berkshires- warm and loved 3 bedroom home, holiday rental in Sheffield

Winter in the Berkshires- warm and loved 3 bedroom home

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

Little House in the Woods

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Ashley Falls Getaway, holiday rental in Sheffield
Charming Ashley Falls Getaway, holiday rental in Sheffield
Charming Ashley Falls Getaway, holiday rental in Sheffield

Charming Ashley Falls Getaway

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

Beautiful Mountainside House with nearby Lake and Hiking Trails

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

COME STAY AT THE SHEFFIELD CHALET!

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

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

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

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

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

Waterfront Sheffield Escape w/ Spacious Yard!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Berkshire County Retreat, holiday rental in Sheffield
Private Berkshire County Retreat, holiday rental in Sheffield
Private Berkshire County Retreat, holiday rental in Sheffield

Private Berkshire County Retreat

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cheerful 3-bedroom cottage with woodstove, holiday rental in Sheffield
Cheerful 3-bedroom cottage with woodstove, holiday rental in Sheffield
Cheerful 3-bedroom cottage with woodstove, holiday rental in Sheffield

Cheerful 3-bedroom cottage with woodstove

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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River Orchard Meadow, holiday rental in Sheffield
River Orchard Meadow, holiday rental in Sheffield
River Orchard Meadow, holiday rental in Sheffield

River Orchard Meadow

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

Serene Berkshire Artist's House

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

Maplewood: Historic home with pool and hot tub

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

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Historic (updated)1812 Federal brick house well situated in Berkshires with pool, holiday rental in Sheffield
Historic (updated)1812 Federal brick house well situated in Berkshires with pool, holiday rental in Sheffield
Historic (updated)1812 Federal brick house well situated in Berkshires with pool, holiday rental in Sheffield

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Private Berkshire County Retreat, holiday rental in Sheffield
Private Berkshire County Retreat, holiday rental in Sheffield
Private Berkshire County Retreat, holiday rental in Sheffield

Private Berkshire County Retreat

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

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

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 30
Match: Sleeps
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Showing results 1-25 of 25
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