Pittsfield Holiday Rentals
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49 rentals in Pittsfield.
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
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Dancing Horse Lodge
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Lakeside Home With Pool-Completely Renovated
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Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake
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Modern 4 bedroom lakefront house in The Berkshires.
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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!
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Apartment Newly Remodeled Super Location
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshire Ski House / Pittsfield
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Renovated Pittsfield Colonial by Evergreen Home
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Spacious Historic Home in the Berkshires!
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Berkshires Colonial on 2 Acres by Evergreen Home
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Modern, Renovated Lakefront Escape
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Hidden Oasis in the Mountains by Evergreen Home
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Elegant Pittsfield Home Near Downtown & Skiing!
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Solomon Ely Homestead - Charming Pittsfield Stay
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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3 Bedroom home w/ lake and mountain views near skiing, and cultural
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Stylish, Centrally Located Berkshires Home-Base
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Charming Apartment In Berkshire Victorian Home
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Lake Views & Dock Access - Pittsfield Cottage!
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshire Mountainside Condo
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stylish Berkshire Apartment conveniently located in the center of town
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Country Living just minutes from Everything!
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Great mountain getaway
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
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A Private 1940s Elegant Estate, renovated to Modern-Day Luxury - Tanglewood
Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 7
Match: Sleeps
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Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
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Chic Pittsfield Home With A View!
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Berkshire Lake Beauty-Modern Amenities On The Lake
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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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Berkshires family fun at Beautiful Hygge House on Richmond Pond- New Deck 2024!
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Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
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Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special
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Cozy Berkshire cottage with fireplace.
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Large, comfortable house and yard located on a beautiful lake.
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house with view in the berkshires
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Tranquil Lake House Getaway on Onota Lake
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Beautiful Waterfront home with deep water dock on Onota Lake
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Charming Berkshire Getaway in a Modern Comfortable House
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ray of Sunshine Berkshire Home on Pontoosuc Lake
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Lake View, Kayaks, Elec Bikes, Hot Tub, Large Open Great Room, Lrg Kitchen
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Family-Friendly Richmond Cottage w/ Private Yard
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Perfect for Winter Skiing!!
Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Richmond Cottage w/ Fire Pit & Furnished Deck!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Escape to your cozy retreat near Pontoosuc Lake and Jiminy Peak
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Cape Home In the Beautiful Berkshires - Near Lenox & Bousquet
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Showing results 1-49 of 49
Frequently Asked Questions about Pittsfield
- Yes, here are some popular holiday rentals in Pittsfield that have a pool:
- Lake Front Home in Heart of the Berkshires Near Jiminy Peak
- Dancing Horse Lodge
- Lakeside Home With Pool-Completely Renovated
- Yes, here are some popular holiday rentals in Pittsfield that have internet access:
- Lake Front Home in Heart of the Berkshires Near Jiminy Peak
- Dancing Horse Lodge
- Lakeside Home With Pool-Completely Renovated
- The best pet friendly rentals in Pittsfield are:
- Dancing Horse Lodge
- Renovated Pittsfield Colonial by Evergreen Home
- Spacious Historic Home in the Berkshires!
- Some of the most popular kid friendly rentals in Pittsfield are:
- Lake Front Home in Heart of the Berkshires Near Jiminy Peak
- Dancing Horse Lodge
- Lakeside Home With Pool-Completely Renovated
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