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Pittsfield Holiday Rentals

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50 rentals in Pittsfield.
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Recently renovated 4 bedroom lakefront house in The Berkshires., holiday rental in Pittsfield

Recently renovated 4 bedroom lakefront house in The Berkshires.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake, holiday rental in Pittsfield

Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything, holiday rental in Pittsfield

A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Tranquil Lake House Getaway on Onota Lake, holiday rental in Pittsfield

Tranquil Lake House Getaway on Onota Lake

5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Berkshire Lake House Vacation Rental, holiday rental in Pittsfield

Berkshire Lake House Vacation Rental

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special, holiday rental in Pittsfield

Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Waterfront home with deep water dock on Onota Lake, holiday rental in Pittsfield

Beautiful Waterfront home with deep water dock on Onota Lake

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b, holiday rental in Pittsfield

Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Grand Colonial Home in the Heart of The Berkshires, holiday rental in Pittsfield

Grand Colonial Home in the Heart of The Berkshires

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Exquisite Apartment in Grand Victorian Home 1, holiday rental in Pittsfield

Exquisite Apartment in Grand Victorian Home 1

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Exquisite Apartment in Grand Victorian 2, holiday rental in Pittsfield

Exquisite Apartment in Grand Victorian 2

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Apartment Newly Remodeled Super Location, holiday rental in Pittsfield

Apartment Newly Remodeled Super Location

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshire Village Carriage House, holiday rental in Pittsfield

Berkshire Village Carriage House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires, holiday rental in Pittsfield

New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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RANKED #1 for 5 STAR REVIEWS covering 355 properties., holiday rental in Pittsfield

RANKED #1 for 5 STAR REVIEWS covering 355 properties.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Warm your heart this holiday season in this cozy cottage next to downtown Lenox., holiday rental in Pittsfield

Warm your heart this holiday season in this cozy cottage next to downtown Lenox.

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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5 STAR! Lenox. Luxury. Location., holiday rental in Pittsfield

5 STAR! Lenox. Luxury. Location.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Heart of Lenox Walk to Town Cozy Cottage!, holiday rental in Pittsfield

Heart of Lenox Walk to Town Cozy Cottage!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Gartner House, a charming home in Lenox, holiday rental in Pittsfield

Gartner House, a charming home in Lenox

4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood, holiday rental in Pittsfield

Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Attn MA residents - Private Ski in/Ski out 4 BR Home on Jiminy Peak, holiday rental in Pittsfield

Attn MA residents - Private Ski in/Ski out 4 BR Home on Jiminy Peak

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Berkshire Cottage on Ashmere Lake, holiday rental in Pittsfield

Berkshire Cottage on Ashmere Lake

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Modern Retreat with Stunning Western Views, holiday rental in Pittsfield

Modern Retreat with Stunning Western Views

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort, holiday rental in Pittsfield

6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND, holiday rental in Pittsfield

SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Morning Face - Berkshire estate with heated pool, views and privacy., holiday rental in Pittsfield

Morning Face - Berkshire estate with heated pool, views and privacy.

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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6BR Berkshire Bliss - 38 private acres - close to skiing and town, holiday rental in Pittsfield

6BR Berkshire Bliss - 38 private acres - close to skiing and town

6 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Mounatin Getaway in the Heart of the Berkshires!, holiday rental in Pittsfield

Mounatin Getaway in the Heart of the Berkshires!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lake House, holiday rental in Pittsfield

Lake House

5 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
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Heart of Lenox, holiday rental in Pittsfield

Heart of Lenox

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE, holiday rental in Pittsfield

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Whitman Woods - A Berkshire Vacation, holiday rental in Pittsfield

Whitman Woods - A Berkshire Vacation

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Restored 1881 Farm House, holiday rental in Pittsfield

Restored 1881 Farm House

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Berkshires Spacious Comfortable Charming Farmhouse, holiday rental in Pittsfield

Berkshires Spacious Comfortable Charming Farmhouse

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bentley/Wyndham Hancock Mass at Jiminy Peak, holiday rental in Pittsfield

Bentley/Wyndham Hancock Mass at Jiminy Peak

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Meadow House 4 bdrm 4 bath house, holiday rental in Pittsfield

The Meadow House 4 bdrm 4 bath house

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Christmas in The Berkshires, holiday rental in Pittsfield

Christmas in The Berkshires

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Thanksgiving week lux condo/4 Berkshires, holiday rental in Pittsfield

Thanksgiving week lux condo/4 Berkshires

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!, holiday rental in Pittsfield

Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Guest House in Dtwn Lenox, Walk to Dining!, holiday rental in Pittsfield

Private Guest House in Dtwn Lenox, Walk to Dining!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA, holiday rental in Pittsfield

Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!, holiday rental in Pittsfield

Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled, holiday rental in Pittsfield

Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, holiday rental in Pittsfield

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Gatehouse on Golden Hill, holiday rental in Pittsfield

The Gatehouse on Golden Hill

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Tentrr Signature Site - Berkshire Mountain Hideaway, holiday rental in Pittsfield

Tentrr Signature Site - Berkshire Mountain Hideaway

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Round Mountain Camp, holiday rental in Pittsfield

Tentrr Signature Site - Round Mountain Camp

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Berkshires Summer Rental -  Lee/Lenox, holiday rental in Pittsfield

Berkshires Summer Rental - Lee/Lenox

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh, holiday rental in Pittsfield

Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh

3 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Lakeside Berkshires Home Near Hiking & Skiing, holiday rental in Pittsfield

NEW! Lakeside Berkshires Home Near Hiking & Skiing

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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