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Sandisfield Holiday Rentals

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50 rentals in Sandisfield.
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Family Friendly Farmhouse in the Berkshires, holiday rental in Sandisfield

Family Friendly Farmhouse in the Berkshires

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns, holiday rental in Sandisfield

Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns

6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - Camping in the Woods of the Berkshires, holiday rental in Sandisfield

Tentrr Signature Site - Camping in the Woods of the Berkshires

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Room to Roam. Modern home with all amenities + sep. cabin on 10+  wooded acres., holiday rental in Sandisfield

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 Sandisfield

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 Sandisfield

Gorgeous Log Cabin in the Berkshires

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!, holiday rental in Sandisfield

Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Woodland Cottage-NEW! Convenient, private, family friendly- see CLEANING DETAILS, holiday rental in Sandisfield

Woodland Cottage-NEW! Convenient, private, family friendly- see CLEANING DETAILS

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spacious waterfront Berkshire home family private get-away, holiday rental in Sandisfield

Spacious waterfront Berkshire home family private get-away

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm., holiday rental in Sandisfield

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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Beautiful four season lakeside log home close to all Berkshires attractions., holiday rental in Sandisfield

Beautiful four season lakeside log home close to all Berkshires attractions.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Southfield Village!, holiday rental in Sandisfield

Beautiful Southfield Village!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Peace And Quiet On The Lake, holiday rental in Sandisfield

Peace And Quiet On The Lake

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Country Retreat With Secluded Tree Top Mountain Views, holiday rental in Sandisfield

Spacious Country Retreat With Secluded Tree Top Mountain Views

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Lake Community - Near Town, Attractions, holiday rental in Sandisfield

Lake Community - Near Town, Attractions

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming cedar shingle cottage, holiday rental in Sandisfield

Charming cedar shingle cottage

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Cozy Berkshire home close to Lake Buel, Butternut and Great Barrington., holiday rental in Sandisfield

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshire lake house on lake Garfield, Monterey MA; private, 4 BR, sleeps 10, holiday rental in Sandisfield

Berkshire lake house on lake Garfield, Monterey MA; private, 4 BR, sleeps 10

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Berkshires Lake Retreat, Beautifully Updated with Mid-Century Style, holiday rental in Sandisfield

Berkshires Lake Retreat, Beautifully Updated with Mid-Century Style

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Berkshires Retreat & Respite ⭐️ Walk to the water. Peaceful, renovated property., holiday rental in Sandisfield

Berkshires Retreat & Respite ⭐️ Walk to the water. Peaceful, renovated property.

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Sunset Place - Modern Lake House on Otis Reservoir - 5 Night Min Stay - Sleeps 6, holiday rental in Sandisfield

Sunset Place - Modern Lake House on Otis Reservoir - 5 Night Min Stay - Sleeps 6

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Converted Berkshire schoolhouse on a quiet river, holiday rental in Sandisfield

Converted Berkshire schoolhouse on a quiet river

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn, holiday rental in Sandisfield

Waterfront Lake Buel Cottage: 7 Mi to Monument Mtn

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood, holiday rental in Sandisfield

Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Konkapot Cottage, Pastoral Bliss With Wide Views, holiday rental in Sandisfield

Konkapot Cottage, Pastoral Bliss With Wide Views

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quiet Comfortable Cabin 5 Min. Walk to Lake, holiday rental in Sandisfield

Quiet Comfortable Cabin 5 Min. Walk to Lake

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Modern Farmhouse in the Southern Berkshires, holiday rental in Sandisfield

Modern Farmhouse in the Southern Berkshires

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Ashley Falls Cottage Retreat, holiday rental in Sandisfield

Charming Ashley Falls Cottage Retreat

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Enjoy horses and the largest recreational lake in Massachusetts, holiday rental in Sandisfield

Enjoy horses and the largest recreational lake in Massachusetts

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!, holiday rental in Sandisfield

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Colebrook Dream, holiday rental in Sandisfield

Colebrook Dream

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Amazing Berkshire Mountains Cabin, holiday rental in Sandisfield

Amazing Berkshire Mountains Cabin

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful Berkshire Home in Private Community, holiday rental in Sandisfield

Beautiful Berkshire Home in Private Community

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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'The Mill River Cabin’ w/ Fireplace & River View!, holiday rental in Sandisfield

'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 Sandisfield

Fabulous Post & Beam Berkshire Rental

0 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES, holiday rental in Sandisfield

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful Lakefront Berkshire Rental, holiday rental in Sandisfield

Beautiful Lakefront Berkshire Rental

5 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Lakeside Berkshire Home, holiday rental in Sandisfield

Spacious Lakeside Berkshire Home

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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East Otis Reservoir Cabin w/ Porch - Walk to Lake!, holiday rental in Sandisfield

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Monterey Home w/ Porch: Walk to Lake Garfield, holiday rental in Sandisfield

Cozy Monterey Home w/ Porch: Walk to Lake Garfield

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Renovated Lakefront House w/ Dock: Pets Welcome!, holiday rental in Sandisfield

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 Sandisfield

Private Home Overlooking Stevens Lake

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Echo Hill, holiday rental in Sandisfield

Tentrr Signature Site - Echo Hill

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Maple Corner Farm's Meadow Site, holiday rental in Sandisfield

Tentrr Signature Site - Maple Corner Farm's Meadow Site

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Running Spring Farm, holiday rental in Sandisfield

Tentrr Signature Site - Running Spring Farm

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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NEW Secluded A-Frame Cabin: Fire Pit, Walk to Lake, holiday rental in Sandisfield

NEW Secluded A-Frame Cabin: Fire Pit, Walk to Lake

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! East Otis Romantic Cottage w/ Deck & BBQ!, holiday rental in Sandisfield

NEW! East Otis Romantic Cottage w/ Deck & BBQ!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ski Retreat -- Private Modern on 40 Acres of Land, holiday rental in Sandisfield

Ski Retreat -- Private Modern on 40 Acres of Land

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Spectacular Fall Foliage in Sheffield  with Monthly Special Pricing Available, holiday rental in Sandisfield

Spectacular Fall Foliage in Sheffield with Monthly Special Pricing Available

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lake house in the heart of the Berkshires, holiday rental in Sandisfield

Lake house in the heart of the Berkshires

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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