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Holiday Rentals in Pittsfield

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37 rentals in Pittsfield.
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Modern 4 bedroom lakefront house in The Berkshires., holiday rental in Pittsfield
Modern 4 bedroom lakefront house in The Berkshires., holiday rental in Pittsfield
Modern 4 bedroom lakefront house in The Berkshires., holiday rental in Pittsfield

Modern 4 bedroom lakefront house in The Berkshires.

Holiday Rental House
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, holiday rental in Pittsfield
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

Holiday Rental House
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, holiday rental in Pittsfield
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

Holiday Rental House
2 bedrooms
3 bathrooms
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, holiday rental in Pittsfield
Tranquil Lake House Getaway on Onota Lake, holiday rental in Pittsfield

Tranquil Lake House Getaway on Onota Lake

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Berkshire Lake House Vacation Rental, holiday rental in Pittsfield
Berkshire Lake House Vacation Rental, holiday rental in Pittsfield
Berkshire Lake House Vacation Rental, holiday rental in Pittsfield

Berkshire Lake House Vacation Rental

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 4
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, holiday rental in Pittsfield
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

Holiday Rental House
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, holiday rental in Pittsfield
Beautiful Waterfront home with deep water dock on Onota Lake, holiday rental in Pittsfield

Beautiful Waterfront home with deep water dock on Onota Lake

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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A Private 1940s Elegant Estate, renovated to Modern-Day Luxury - Tanglewood, holiday rental in Pittsfield
A Private 1940s Elegant Estate, renovated to Modern-Day Luxury - Tanglewood, holiday rental in Pittsfield
A Private 1940s Elegant Estate, renovated to Modern-Day Luxury - Tanglewood, holiday rental in Pittsfield

A Private 1940s Elegant Estate, renovated to Modern-Day Luxury - Tanglewood

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 9
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, holiday rental in Pittsfield
Grand Colonial Home in the Heart of The Berkshires, holiday rental in Pittsfield

Grand Colonial Home in the Heart of The Berkshires

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
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, holiday rental in Pittsfield
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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Lakeside Home With Pool-Completely Renovated, holiday rental in Pittsfield
Lakeside Home With Pool-Completely Renovated, holiday rental in Pittsfield
Lakeside Home With Pool-Completely Renovated, holiday rental in Pittsfield

Lakeside Home With Pool-Completely Renovated

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Richmond Pond Beauty, holiday rental in Pittsfield
Richmond Pond Beauty, holiday rental in Pittsfield
Richmond Pond Beauty, holiday rental in Pittsfield

Richmond Pond Beauty

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Lovely ranch home getaway in Berkshire County, holiday rental in Pittsfield
Lovely ranch home getaway in Berkshire County, holiday rental in Pittsfield
Lovely ranch home getaway in Berkshire County, holiday rental in Pittsfield

Lovely ranch home getaway in Berkshire County

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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SAFE AND COZY BERKSHIRES GETAWAY, holiday rental in Pittsfield
SAFE AND COZY BERKSHIRES GETAWAY, holiday rental in Pittsfield
SAFE AND COZY BERKSHIRES GETAWAY, holiday rental in Pittsfield

SAFE AND COZY BERKSHIRES GETAWAY

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Historic Home Close to Downtown & Skiing!, holiday rental in Pittsfield
Charming Historic Home Close to Downtown & Skiing!, holiday rental in Pittsfield
Charming Historic Home Close to Downtown & Skiing!, holiday rental in Pittsfield

Charming Historic Home Close to Downtown & Skiing!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Dancing Horse Lodge, holiday rental in Pittsfield
Dancing Horse Lodge, holiday rental in Pittsfield
Dancing Horse Lodge, holiday rental in Pittsfield

Dancing Horse Lodge

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Exquisite Apartment in Grand Victorian Home 1, holiday rental in Pittsfield
Exquisite Apartment in Grand Victorian Home 1, holiday rental in Pittsfield
Exquisite Apartment in Grand Victorian Home 1, holiday rental in Pittsfield

Exquisite Apartment in Grand Victorian Home 1

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Lake Life in Berkshires at Family Friendly Hygge House, holiday rental in Pittsfield
Lake Life in Berkshires at Family Friendly Hygge House, holiday rental in Pittsfield
Lake Life in Berkshires at Family Friendly Hygge House, holiday rental in Pittsfield

Lake Life in Berkshires at Family Friendly Hygge House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Honeysuckle Rose Cottage, holiday rental in Pittsfield
Honeysuckle Rose Cottage, holiday rental in Pittsfield
Honeysuckle Rose Cottage, holiday rental in Pittsfield

Honeysuckle Rose Cottage

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Central Berkshire Bungalow, Long Term Availability, holiday rental in Pittsfield
Central Berkshire Bungalow, Long Term Availability, holiday rental in Pittsfield
Central Berkshire Bungalow, Long Term Availability, holiday rental in Pittsfield

Central Berkshire Bungalow, Long Term Availability

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Hidden Oasis in the Berkshire Mountains, holiday rental in Pittsfield
Hidden Oasis in the Berkshire Mountains, holiday rental in Pittsfield
Hidden Oasis in the Berkshire Mountains, holiday rental in Pittsfield

Hidden Oasis in the Berkshire Mountains

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Berkshire Home Near Jiminy Peak| A Great Location!, holiday rental in Pittsfield
Berkshire Home Near Jiminy Peak| A Great Location!, holiday rental in Pittsfield
Berkshire Home Near Jiminy Peak| A Great Location!, holiday rental in Pittsfield

Berkshire Home Near Jiminy Peak| A Great Location!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cozy Berkshire cottage with fireplace., holiday rental in Pittsfield
Cozy Berkshire cottage with fireplace., holiday rental in Pittsfield
Cozy Berkshire cottage with fireplace., holiday rental in Pittsfield

Cozy Berkshire cottage with fireplace.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Exquisite Apartment in Grand Victorian 2, holiday rental in Pittsfield
Exquisite Apartment in Grand Victorian 2, holiday rental in Pittsfield
Exquisite Apartment in Grand Victorian 2, holiday rental in Pittsfield

Exquisite Apartment in Grand Victorian 2

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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MEMORIAL DAY WEEK THRU 6/30 AVAILABLE!!!, holiday rental in Pittsfield
MEMORIAL DAY WEEK THRU 6/30 AVAILABLE!!!, holiday rental in Pittsfield
MEMORIAL DAY WEEK THRU 6/30 AVAILABLE!!!, holiday rental in Pittsfield

MEMORIAL DAY WEEK THRU 6/30 AVAILABLE!!!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
More info
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Berkshire Ski House / Pittsfield, holiday rental in Pittsfield
Berkshire Ski House / Pittsfield, holiday rental in Pittsfield
Berkshire Ski House / Pittsfield, holiday rental in Pittsfield

Berkshire Ski House / Pittsfield

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Home away from Home in the Berkshires, holiday rental in Pittsfield
Home away from Home in the Berkshires, holiday rental in Pittsfield
Home away from Home in the Berkshires, holiday rental in Pittsfield

Home away from Home in the Berkshires

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Great mountain getaway, holiday rental in Pittsfield
Great mountain getaway, holiday rental in Pittsfield
Great mountain getaway, holiday rental in Pittsfield

Great mountain getaway

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Perfect for Winter Skiing!!, holiday rental in Pittsfield
Perfect for Winter Skiing!!, holiday rental in Pittsfield
Perfect for Winter Skiing!!, holiday rental in Pittsfield

Perfect for Winter Skiing!!

Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Condo Resort in Cultural Art Haven, Berkshire, holiday rental in Pittsfield
Condo Resort in Cultural Art Haven, Berkshire, holiday rental in Pittsfield
Condo Resort in Cultural Art Haven, Berkshire, holiday rental in Pittsfield

Condo Resort in Cultural Art Haven, Berkshire

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Fully Equipped Spacious Family Home in The Berkshires, holiday rental in Pittsfield
Fully Equipped Spacious Family Home in The Berkshires, holiday rental in Pittsfield
Fully Equipped Spacious Family Home in The Berkshires, holiday rental in Pittsfield

Fully Equipped Spacious Family Home in The Berkshires

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Ski the Berkshires!, holiday rental in Pittsfield
Ski the Berkshires!, holiday rental in Pittsfield
Ski the Berkshires!, holiday rental in Pittsfield

Ski the Berkshires!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Berkshire Winter and Summer Getaway, holiday rental in Pittsfield
Berkshire Winter and Summer Getaway, holiday rental in Pittsfield
Berkshire Winter and Summer Getaway, holiday rental in Pittsfield

Berkshire Winter and Summer Getaway

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Spacious Berkshire Colonial On Private 2.7 Acres, holiday rental in Pittsfield
Spacious Berkshire Colonial On Private 2.7 Acres, holiday rental in Pittsfield
Spacious Berkshire Colonial On Private 2.7 Acres, holiday rental in Pittsfield

Spacious Berkshire Colonial On Private 2.7 Acres

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Charming Berkshire Getaway in a Modern Comfortable House, holiday rental in Pittsfield
Charming Berkshire Getaway in a Modern Comfortable House, holiday rental in Pittsfield
Charming Berkshire Getaway in a Modern Comfortable House, holiday rental in Pittsfield

Charming Berkshire Getaway in a Modern Comfortable House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lake Front Home in Heart of the Berkshires Near Jiminy Peak, holiday rental in Pittsfield
Lake Front Home in Heart of the Berkshires Near Jiminy Peak, holiday rental in Pittsfield
Lake Front Home in Heart of the Berkshires Near Jiminy Peak, holiday rental in Pittsfield

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Charming Apartment In Berkshire Victorian Home, holiday rental in Pittsfield
Charming Apartment In Berkshire Victorian Home, holiday rental in Pittsfield
Charming Apartment In Berkshire Victorian Home, holiday rental in Pittsfield

Charming Apartment In Berkshire Victorian Home

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
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