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Sheffield Holiday Rentals

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50 rentals in Sheffield.
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Close To Skiing!  Beautiful +Family Friendly - W Tree House & Tennis Court, holiday rental in Sheffield

Close To Skiing! Beautiful +Family Friendly - W Tree House & Tennis Court

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Antique Farmhouse Totally Restored, holiday rental in Sheffield

Antique Farmhouse Totally Restored

4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Spacious Country Retreat With Secluded Tree Top Mountain Views, holiday rental in Sheffield

Spacious Country Retreat With Secluded Tree Top Mountain Views

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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The Little House in the Woods, holiday rental in Sheffield

The Little House in the Woods

2 bedrooms
2 bathrooms
Sleeps 6
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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Berkshire Home - Enjoy all Summer, Fall & Winter Attractions, holiday rental in Sheffield

Beautiful Berkshire Home - Enjoy all Summer, Fall & Winter Attractions

3 bedrooms
3 bathrooms
Sleeps 6
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

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Newly Renovated Country Retreat-Berkshires, holiday rental in Sheffield

Newly Renovated Country Retreat-Berkshires

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Large Country Home, Sleeps 10! Enjoy the Firepit and Ski Butternut, holiday rental in Sheffield

Large Country Home, Sleeps 10! Enjoy the Firepit and Ski Butternut

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spectacular Fall Foliage in Sheffield  with Monthly Special Pricing Available, holiday rental in Sheffield

Spectacular Fall Foliage in Sheffield with Monthly Special Pricing Available

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Room to Roam. Modern home with all amenities + sep. cabin on 10+  wooded acres., holiday rental in Sheffield

Room to Roam. Modern home with all amenities + sep. cabin on 10+ wooded acres.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private rustic cottage with lake access, holiday rental in Sheffield

Private rustic cottage with lake access

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Gorgeous Log Cabin in the Berkshires, holiday rental in Sheffield

Gorgeous Log Cabin in the Berkshires

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!, holiday rental in Sheffield

The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Downtown GB apartment walk to shops and restaurants, holiday rental in Sheffield

Downtown GB apartment walk to shops and restaurants

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm., holiday rental in Sheffield

Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Stunning Renovated Victorian, holiday rental in Sheffield

Stunning Renovated Victorian

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Southfield Village!, holiday rental in Sheffield

Beautiful Southfield Village!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful home with all amenities. Close to everything. Fiber optic internet., holiday rental in Sheffield

Beautiful home with all amenities. Close to everything. Fiber optic internet.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Berkshires: Romantic Cottage with spectacular view, holiday rental in Sheffield

Berkshires: Romantic Cottage with spectacular view

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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North Canaan's Quiet & Cozy Home, holiday rental in Sheffield

North Canaan's Quiet & Cozy Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lake Community - Near Town, Attractions, holiday rental in Sheffield

Lake Community - Near Town, Attractions

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW SECLUDED 3 BEDROOM COUNTRY CASTLE, holiday rental in Sheffield

NEW SECLUDED 3 BEDROOM COUNTRY CASTLE

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Berkshire home close to Lake Buel, Butternut and Great Barrington., holiday rental in Sheffield

Cozy Berkshire home close to Lake Buel, Butternut and Great Barrington.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Barn Apartment in Gorgeous Stonybrook Farm, holiday rental in Sheffield

Barn Apartment in Gorgeous Stonybrook Farm

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Converted Berkshire schoolhouse on a quiet river, holiday rental in Sheffield

Converted Berkshire schoolhouse on a quiet river

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington, holiday rental in Sheffield

Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Gem of the Berkshires, walk to downtown & lake., holiday rental in Sheffield

Gem of the Berkshires, walk to downtown & lake.

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn, holiday rental in Sheffield

Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Modern Victorian on the Hill, holiday rental in Sheffield

Modern Victorian on the Hill

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Modern Farmhouse in the Southern Berkshires, holiday rental in Sheffield

Modern Farmhouse in the Southern Berkshires

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Premier Waterfront Home!, holiday rental in Sheffield

Premier Waterfront Home!

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Ashley Falls Cottage Retreat, holiday rental in Sheffield

Charming Ashley Falls Cottage Retreat

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Great Barrington - The Cottage at Windflower Inn - Low Price - Close to Skiing, holiday rental in Sheffield

Great Barrington - The Cottage at Windflower Inn - Low Price - Close to Skiing

0 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Charming 2+2 Lakeside Cottage on Best Lake in CT, holiday rental in Sheffield

Charming 2+2 Lakeside Cottage on Best Lake in CT

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!, holiday rental in Sheffield

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Eco-friendly cozy home in Gt. Barrington, holiday rental in Sheffield

Eco-friendly cozy home in Gt. Barrington

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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'The Mill River Cabin’ w/ Fireplace & River View!, holiday rental in Sheffield

'The Mill River Cabin’ w/ Fireplace & River View!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Fabulous Post & Beam Berkshire Rental, holiday rental in Sheffield

Fabulous Post & Beam Berkshire Rental

0 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Renovated Lakefront House w/ Dock: Pets Welcome!, holiday rental in Sheffield

Renovated Lakefront House w/ Dock: Pets Welcome!

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Private Home Overlooking Stevens Lake, holiday rental in Sheffield

Private Home Overlooking Stevens Lake

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Impeccable House Minutes from Downtown Great Barrington, holiday rental in Sheffield

Impeccable House Minutes from Downtown Great Barrington

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Echo Hill, holiday rental in Sheffield

Tentrr Signature Site - Echo Hill

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Konkapot Cottage, Pastoral Bliss With Wide Views, holiday rental in Sheffield

Konkapot Cottage, Pastoral Bliss With Wide Views

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Cozy Great Barrington Home 1 Mi to Ski Resort, holiday rental in Sheffield

NEW! Cozy Great Barrington Home 1 Mi to Ski Resort

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Ski Retreat -- Private Modern on 40 Acres of Land, holiday rental in Sheffield

Ski Retreat -- Private Modern on 40 Acres of Land

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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NEW! Serene Great Barrington Cottage w/ Fire Pit!, holiday rental in Sheffield

NEW! Serene Great Barrington Cottage w/ Fire Pit!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - Taconic State Park: High Valley Rd Site A, holiday rental in Sheffield

Tentrr State Park Site - Taconic State Park: High Valley Rd Site A

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr State Park Site - Taconic State Park: High Valley Rd Site D, holiday rental in Sheffield

Tentrr State Park Site - Taconic State Park: High Valley Rd Site D

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!, holiday rental in Sheffield

Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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