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Pittsfield
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Pittsfield, MA Accommodation and Villas
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Internet or Wifi (48)
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Kid friendly (45)
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Distance from
5 km
Hancock Shaker Village
Barrington Stage Company
Herman Melville's Arrowhead
Colonial Theatre
Mass Audubon Canoe Meadows Wildlife Sanctuary
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49 rentals
in Pittsfield.
Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake
72 reviews
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 14
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Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Holiday Rental House
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8 bedrooms
3 bathrooms
Sleeps 25
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Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
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Tranquil Lake House Getaway on Onota Lake
50 reviews
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 10
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A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything
74 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
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Dancing Horse Lodge
3 reviews
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Country Living just minutes from everything!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Richmond Pond Beauty
7 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 7
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Chic Pittsfield Home With A View!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Cozy Berkshire cottage with fireplace.
2 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 5
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Lakeside Home With Pool-Completely Renovated
6 reviews
Holiday Rental House
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6 bedrooms
5 bathrooms
Sleeps 16
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Enjoy Big City Vibes at City Place in the heart of the Berkshires!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 7
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Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 14
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Modern 4 bedroom lakefront house in The Berkshires.
8 reviews
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Beautiful, Newly Renovated Apartment in a Great Location
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Cozy Renovated with 1 parking space
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Historical Colonial Near Down Town
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
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Apartment Newly Remodeled Super Location
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Serene Retreat in the Scenic Berkshire Mountains
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Condo Resort in Cultural Art Haven, Berkshire
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special
9 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Central Berkshire Bungalow, Long Term Availability
3 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 5
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SAFE AND COZY BERKSHIRES GETAWAY
5 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Lovely ranch home getaway in Berkshire County
6 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Traveling Nurses! Paradise, 0.2 Miles from BMC - 3 Bedroom
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 3
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Berkshire Ski House / Pittsfield
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Stylish cottage located by Pontoosuc Lake with lake views!
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Charming Apartment In Berkshire Victorian Home
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 8
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Beautiful Waterfront home with deep water dock on Onota Lake
64 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 10
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Summer in the Berkshires at Family Friendly Hygge House
5 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
7 reviews
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 7
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Fully Equipped Spacious Family Home in The Berkshires
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 7
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Berkshire Mountainside Condo
Condo/Apartment
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3 bedrooms
3 bathrooms
Sleeps 8
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Lovely Family Retreat in the ♥️ of the Berkshires!
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 7
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Cape Home In the Beautiful Berkshires - Near Bousquet
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 10
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Berkshire Lake House vacation home
10 reviews
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
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Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 10
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A Cozy 100 yr old New England Berkshires Dutch Colonial. Long term available.
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Renovated Colonial in the Heart of The Berkshires
5 reviews
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 12
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Spacious Historic Home in the Berkshires!
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 9
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Beautiful Home away from Home
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
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Spacious Berkshire Colonial On Private 2.7 Acres
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
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East Beach Lakehouse, modern lakefront getaway
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 9
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Perfect for Winter Skiing!!
Condo/Apartment
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4 bedrooms
4 bathrooms
Sleeps 8
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Hidden Oasis in the Berkshire Mountains
2 reviews
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
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Great mountain getaway
Holiday Rental House
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6 bedrooms
4 bathrooms
Sleeps 8
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A Private 1940s Elegant Estate, renovated to Modern-Day Luxury - Tanglewood
23 reviews
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 9
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The Nest at Birdland
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Showing results 1-49 of 49
Frequently Asked Questions about Pittsfield
Do any holiday rentals in Pittsfield have a pool?
Yes, here are some popular holiday rentals in Pittsfield that have a pool:
Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
See all holiday rentals with a pool in Pittsfield on Tripadvisor
Do any holiday rentals in Pittsfield have internet access?
Yes, here are some popular holiday rentals in Pittsfield that have internet access:
Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
See all holiday rentals in Pittsfield on Tripadvisor
What are the best pet friendly rentals in Pittsfield?
The best pet friendly rentals in Pittsfield are:
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Dancing Horse Lodge
Chic Pittsfield Home With A View!
See all pet friendly holiday rentals in Pittsfield on Tripadvisor
What are some great rentals in Pittsfield that are kid friendly?
Some of the most popular kid friendly rentals in Pittsfield are:
Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
See all kid friendly holiday rentals in Pittsfield on Tripadvisor