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Vacation rentals in Pittsfield, MA

Find deals on 49 vacation rentals in Pittsfield, MA

Pittsfield, MA, United States
7 May — 8 May2

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Top rentals in Pittsfield

Find the perfect vacation rental for your stay in Pittsfield
Price
C$ 117
C$ 1,341
Review Score
0+
6+
7+
8+
9+

Hostels and cheap hotels in Pittsfield

These hotels and hostels usually make for a cheap way to stay in Pittsfield
Apartment Newly Remodeled Super Location Photo

Apartment Newly Remodeled Super Location

Pittsfield, MA, United States

10.0
C$ 117
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Wow-New Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk Photo

Wow-New Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk

Hancock, MA, United States

8.1
C$ 200
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Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cummington, MA, United States

C$ 131
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Wyndham Bentley Brook Studio, In & Out Ski Resort At Jiminy Peak

Lanesborough, MA, United States

C$ 201
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Unique and Eclectic Small Town Suite Rental in Massachusetts

Cummington, MA, United States

C$ 164
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Cozy Renovated with 1 parking space Photo

Cozy Renovated with 1 parking space

Pittsfield, MA, United States

C$ 218
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Get the best value vacation rental in Pittsfield

These Pittsfield vacation rentals have the best prices for their ratings
Water Street Apartments Photo

Water Street Apartments

Williamstown, MA, United States

9.4
C$ 261
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Berkshire Vacation Rentals: Chic Pittsfield Home With A View Photo

Berkshire Vacation Rentals: Chic Pittsfield Home With A View

Pittsfield, MA, United States

9.0
C$ 449
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Wow-New Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk Photo

Wow-New Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk

Hancock, MA, United States

8.1
C$ 200
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Urban Peak Escape Photo

Urban Peak Escape

Lenox, MA, United States

10.0
C$ 764
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Pittsfield Home with Deck - 12 Mi to Jiminy Peak! Photo

Pittsfield Home with Deck - 12 Mi to Jiminy Peak!

Pittsfield, MA, United States

9.0
C$ 413
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Berkshire Lake Beauty-Modern Amenities On The Lake Photo

Berkshire Lake Beauty-Modern Amenities On The Lake

Pittsfield, MA, United States

9.9
C$ 911
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momondo's favourite vacation rentals in Pittsfield

Learn more about these user-preferred vacation rentals in Pittsfield
Wow-New Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk Photo

Wow-New Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk

Hancock, MA, United States

8.1
C$ 200
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions! Photo

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield, MA, United States

C$ 525
Solomon Ely Homestead - Charming Pittsfield Stay Photo

Solomon Ely Homestead - Charming Pittsfield Stay

Pittsfield, MA, United States

C$ 514

Mounatin Getaway In The Heart Of The Berkshires!

Lanesborough, MA, United States

9.5
C$ 662
Charming Apartment In Berkshire Victorian Home Photo

Charming Apartment In Berkshire Victorian Home

Pittsfield, MA, United States

6.0
C$ 510
Perfect for Winter Skiing!! Photo

Perfect for Winter Skiing!!

Pittsfield, MA, United States

C$ 1,049
Berkshire Vacation Rentals: Chic Pittsfield Home With A View Photo

Berkshire Vacation Rentals: Chic Pittsfield Home With A View

Pittsfield, MA, United States

9.0
C$ 449

Beautiful Cottage Rental on Lakeside Property in The Berkshires, Massachusetts

Lanesborough, MA, United States

C$ 860

Impressive Family-Friendly Lake Cottage in The Berkshires, Massachusetts

Lanesborough, MA, United States

C$ 735

Spacious Guest Cottage Rental on Lake in The Berkshires, Massachusetts

Lanesborough, MA, United States

C$ 860
Family-Friendly Richmond Cottage with Private Yard Photo

Family-Friendly Richmond Cottage with Private Yard

Pittsfield, MA, United States

9.0
C$ 821

Lake Views and Dock Access - Pittsfield Cottage!

Pittsfield, MA, United States

C$ 495
Urban Peak Escape Photo

Urban Peak Escape

Lenox, MA, United States

10.0
C$ 764
Elegant 19th Century New England Newly Renovated 1br Vacation Rental Photo

Elegant 19th Century New England Newly Renovated 1br Vacation Rental

Lee, MA, United States

10.0
C$ 258

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough, MA, United States

9.6
C$ 287
Pittsfield Home with Deck - 12 Mi to Jiminy Peak! Photo

Pittsfield Home with Deck - 12 Mi to Jiminy Peak!

Pittsfield, MA, United States

9.0
C$ 413

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cummington, MA, United States

C$ 131

Unique and Eclectic Small Town Suite Rental in Massachusetts

Cummington, MA, United States

C$ 164
Water Street Apartments Photo

Water Street Apartments

Williamstown, MA, United States

9.4
C$ 261
New Reno - Chalet-Style Farm Loft Near Tanglewood Photo

New Reno - Chalet-Style Farm Loft Near Tanglewood

New Lebanon, NY, United States

C$ 231

Useful insights on Pittsfield vacation rentals

Get a quick overview on price and accommodation trends for your visit in Pittsfield

Lowest Vacation Rental Price

C$ 117
The cheapest price for a room in Pittsfield found in the last 7 days is C$ 117/night. This rate is available with Apartment Newly Remodeled Super Location.

When to book a vacation rental in Pittsfield

Check out the information below to find the best deal on a vacation rental in Pittsfield
Cheapest day of weekWednesdayis the cheapest day of the week to book
Highest day of weekSundayis the most expensive day of the week to book
C$ 155
C$ 656

Information about staying in Pittsfield

Read these important travel tips before booking a vacation rental in Pittsfield

When is the best time to book a vacation rental in Pittsfield?

If you can be flexible on booking dates, vacation apartments and rental properties in Pittsfield can be as much as 51% cheaper in May.

How many operators does momondo search for hotels in Pittsfield?

As of April 2025, there are 61 operators available to choose from for hotels in Pittsfield.

When did momondo last update prices for hotels in Pittsfield?

Prices for hotels in Pittsfield were last updated today.

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