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Holiday Rentals in Pittsfield

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Bathrooms

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5 km
48 rentals 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 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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Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, holiday rental in Pittsfield
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, holiday rental in Pittsfield
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, holiday rental in Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Holiday Rental House
8 bedrooms
3 bathrooms
Sleeps 25
Match: Sleeps
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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
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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
2 bathrooms
Sleeps 10
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
1 bathroom
Sleeps 5
Match: Sleeps
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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
1 bathroom
Sleeps 6
Match: Sleeps
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Country Living just minutes from everything!, holiday rental in Pittsfield
Country Living just minutes from everything!, holiday rental in Pittsfield
Country Living just minutes from everything!, holiday rental in Pittsfield

Country Living just minutes from everything!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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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Chic Pittsfield Home With A View!, holiday rental in Pittsfield
Chic Pittsfield Home With A View!, holiday rental in Pittsfield
Chic Pittsfield Home With A View!, holiday rental in Pittsfield

Chic Pittsfield Home With A View!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
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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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Enjoy Big City Vibes at City Place in the heart of the Berkshires!, holiday rental in Pittsfield
Enjoy Big City Vibes at City Place in the heart of the Berkshires!, holiday rental in Pittsfield
Enjoy Big City Vibes at City Place in the heart of the Berkshires!, holiday rental in Pittsfield

Enjoy Big City Vibes at City Place in the heart of the Berkshires!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake, holiday rental in Pittsfield
Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake, holiday rental in Pittsfield
Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake, holiday rental in Pittsfield

Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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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
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful, Newly Renovated Apartment in a Great Location, holiday rental in Pittsfield
Beautiful, Newly Renovated Apartment in a Great Location, holiday rental in Pittsfield
Beautiful, Newly Renovated Apartment in a Great Location, holiday rental in Pittsfield

Beautiful, Newly Renovated Apartment in a Great Location

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Renovated with 1 parking space, holiday rental in Pittsfield
Cozy Renovated with 1 parking space, holiday rental in Pittsfield
Cozy Renovated with 1 parking space, holiday rental in Pittsfield

Cozy Renovated with 1 parking space

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!, holiday rental in Pittsfield
Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!, holiday rental in Pittsfield
Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!, holiday rental in Pittsfield

Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Apartment Newly Remodeled Super Location, holiday rental in Pittsfield
Apartment Newly Remodeled Super Location, holiday rental in Pittsfield
Apartment Newly Remodeled Super Location, holiday rental in Pittsfield

Apartment Newly Remodeled Super Location

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Serene Retreat in the Scenic Berkshire Mountains, holiday rental in Pittsfield
Serene Retreat in the Scenic Berkshire Mountains, holiday rental in Pittsfield
Serene Retreat in the Scenic Berkshire Mountains, holiday rental in Pittsfield

Serene Retreat in the Scenic Berkshire Mountains

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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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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
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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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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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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
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
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Stylish cottage located by Pontoosuc Lake with lake views!, holiday rental in Pittsfield
Stylish cottage located by Pontoosuc Lake with lake views!, holiday rental in Pittsfield
Stylish cottage located by Pontoosuc Lake with lake views!, holiday rental in Pittsfield

Stylish cottage located by Pontoosuc Lake with lake views!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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
2 bathrooms
Sleeps 8
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
More info
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Summer in the Berkshires at Family Friendly Hygge House, holiday rental in Pittsfield
Summer in the Berkshires at Family Friendly Hygge House, holiday rental in Pittsfield
Summer in the Berkshires at Family Friendly Hygge House, holiday rental in Pittsfield

Summer in the Berkshires at Family Friendly Hygge House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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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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
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Berkshire Mountainside Condo, holiday rental in Pittsfield
Berkshire Mountainside Condo, holiday rental in Pittsfield
Berkshire Mountainside Condo, holiday rental in Pittsfield

Berkshire Mountainside Condo

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lovely Family Retreat in the ♥️ of the Berkshires!, holiday rental in Pittsfield
Lovely Family Retreat in the ♥️ of the Berkshires!, holiday rental in Pittsfield
Lovely Family Retreat in the ♥️ of the Berkshires!, holiday rental in Pittsfield

Lovely Family Retreat in the ♥️ of the Berkshires!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Cape Home In the Beautiful Berkshires - Near Bousquet, holiday rental in Pittsfield
Cape Home In the Beautiful Berkshires - Near Bousquet, holiday rental in Pittsfield
Cape Home In the Beautiful Berkshires - Near Bousquet, holiday rental in Pittsfield

Cape Home In the Beautiful Berkshires - Near Bousquet

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Berkshire Lake House vacation home, holiday rental in Pittsfield
Berkshire Lake House vacation home, holiday rental in Pittsfield
Berkshire Lake House vacation home, holiday rental in Pittsfield

Berkshire Lake House vacation home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!, holiday rental in Pittsfield
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!, holiday rental in Pittsfield
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!, holiday rental in Pittsfield

Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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A Cozy 100 yr old New England Berkshires Dutch Colonial.

Long term available., holiday rental in Pittsfield
A Cozy 100 yr old New England Berkshires Dutch Colonial.

Long term available., holiday rental in Pittsfield
A Cozy 100 yr old New England Berkshires Dutch Colonial.

Long term available., holiday rental in Pittsfield

A Cozy 100 yr old New England Berkshires Dutch Colonial. Long term available.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ski Jiminy, Hot Tub, Large Open Great Room, Lake View, holiday rental in Pittsfield
Ski Jiminy, Hot Tub, Large Open Great Room, Lake View, holiday rental in Pittsfield
Ski Jiminy, Hot Tub, Large Open Great Room, Lake View, holiday rental in Pittsfield

Ski Jiminy, Hot Tub, Large Open Great Room, Lake View

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Renovated Colonial in the Heart of The Berkshires, holiday rental in Pittsfield
Renovated Colonial in the Heart of The Berkshires, holiday rental in Pittsfield
Renovated Colonial in the Heart of The Berkshires, holiday rental in Pittsfield

Renovated Colonial in the Heart of The Berkshires

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Spacious Historic Home in the Berkshires!, holiday rental in Pittsfield
Spacious Historic Home in the Berkshires!, holiday rental in Pittsfield
Spacious Historic Home in the Berkshires!, holiday rental in Pittsfield

Spacious Historic Home in the Berkshires!

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Beautiful Home away from Home, holiday rental in Pittsfield
Beautiful Home away from Home, holiday rental in Pittsfield
Beautiful Home away from Home, holiday rental in Pittsfield

Beautiful Home away from Home

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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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
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East Beach Lakehouse, modern lakefront getaway, holiday rental in Pittsfield
East Beach Lakehouse, modern lakefront getaway, holiday rental in Pittsfield
East Beach Lakehouse, modern lakefront getaway, holiday rental in Pittsfield

East Beach Lakehouse, modern lakefront getaway

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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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
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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 10
Match: Sleeps
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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
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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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The Nest at Birdland, holiday rental in Pittsfield
The Nest at Birdland, holiday rental in Pittsfield
The Nest at Birdland, holiday rental in Pittsfield

The Nest at Birdland

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Showing results 1-48 of 48
Frequently Asked Questions about Pittsfield