104+ Rental Villas and Private Getaways in Pittsfield |
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Pittsfield Vacation Rentals & One Degree Stays Homes

About Pittsfield Vacation Rentals

There are more than 104 vacation rentals that are available in Pittsfield. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Pittsfield.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Pittsfield, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Pittsfield. Places to stay near Pittsfield are 1168.68 ft² on average, with prices averaging US $386 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Pittsfield with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Pittsfield

Type Count
Vacation Homes 61
Holiday Apartments 11
Cottages 4

Use these Quick Filters to Find a Vacation Rental in Pittsfield

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Pittsfield.

Weather in Pittsfield, MA

View the weather forecast for Pittsfield before booking your Pittsfield Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Pittsfield, MA

OneDegreeStays offers a large selection of top attractions around Pittsfield. Research things to do on your vacation before you visit Pittsfield.


Bousquet Ski Area
Berkshire Museum
Hancock Shaker Village
Pittsfield State Forest
Colonial Theater
Canoe Meadows Wildlife Sanctuary
Berkshire Athenaeum
Herman Melville's Arrowhead
Guido's Marketplace
Barrington Stage Company
Crane Museum of Papermaking
Arrowhead Museum
Jiminy Peak Mountain Resort
Tanglewood Music Center
Mass MoCA
Williams College
Ski Butternut
Catamount Ski Area
Berkshire East Ski Resort
Norman Rockwell Museum

Other Places to Stay in Pittsfield, MA


Pittsfield State Forest 376 Properties
Bousquet Ski Area 128 Properties
Guido's Marketplace 120 Properties
Arrowhead Museum 108 Properties
Herman Melville's Arrowhead 105 Properties
Colonial Theater 98 Properties
Canoe Meadows Wildlife Sanctuary 92 Properties
Berkshire Museum 89 Properties
Berkshire Athenaeum 79 Properties
Crane Museum of Papermaking 77 Properties
Barrington Stage Company 74 Properties
Hancock Shaker Village 42 Properties

Frequently Asked Questions About Pittsfield?

What are the top vacation rentals in Pittsfield?

There are a lot of options in Pittsfield. If you plan on staying in the Pittsfield area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pittsfield:

How many vacation rentals have private pools in Pittsfield?

There are 1 vacation rentals with private pools near Pittsfield. Top-rated ODS homes that have access to a swimming pool include:

Which vacation homes in Pittsfield are best for families?

If you are looking for a family-friendly vacation home in Pittsfield, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pittsfield:

How many onedegreestays vacation rentals are available in Pittsfield?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 104 in the Pittsfield area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Pittsfield. 


People Also Ask

There are 104 Pittsfield, MA Vacation Rentals

Recently Booked Vacation Rentals in Pittsfield