106+ Vacation Rentals in Pittsfield |
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  3. Pittsfield

Pittsfield Vacation Rentals, Hotels, & Places to Stay

About Pittsfield Vacation Rentals

There are more than 106 places to stay that are available in Pittsfield. These choices include hotels as well as other short-term private accommodations (including vacation rentals, cabins, condos, RVs, and more), have a wide selection of amenities at great prices, providing you with all the comforts of home or a touch of luxury. We like to help you find more room with Varoom when booking your property in Pittsfield.

Varoom features many last-minute deals on hotels, resorts and places to stay including many that are nearby. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Varoom's places in Pittsfield, you have the flexibility of comparing different options from multiple suppliers with a single click. Group deals, private pools, hot tubs, allows pets, or even those with huge master suite bedrooms with open-air showers? You can find vacation rentals and resorts as well as Airbnb-style properties in Pittsfield. Places to stay near Pittsfield are 1164.12 ft² on average, with prices averaging US $385 a night.

Varoom helps you discover places to stay and suggests things to do to create great travel memories in Pittsfield. Prices listed are often found to be at a 30-40% discount versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Rental Accommodation Types in Pittsfield

Type Count
Vacation Homes 63
Holiday Apartments 10
Cottages 4

Use these Quick Filters to Find a Vacation Rental in Pittsfield

★ Pro Tip: Varoom is a meta travel and activities site, and as such we combine results from many of the leading travel websites, helping you compare the best places to stay and things to do in each market. Use the filter option to narrow down your selection and let us help you find more room to stay, play, and discover. Create new memories in Pittsfield today.

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

Varoom 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 463 Properties
Guido's Marketplace 122 Properties
Bousquet Ski Area 120 Properties
Herman Melville's Arrowhead 92 Properties
Arrowhead Museum 92 Properties
Colonial Theater 89 Properties
Berkshire Museum 87 Properties
Berkshire Athenaeum 84 Properties
Canoe Meadows Wildlife Sanctuary 83 Properties
Barrington Stage Company 81 Properties
Crane Museum of Papermaking 77 Properties
Hancock Shaker Village 49 Properties

Complexes around Pittsfield, MA


Hilton Garden Inn Pittsfield 3 Properties

Frequently Asked Questions About Pittsfield?

What are the top vacation rentals in Pittsfield?

We have scoured the web to find you options in Pittsfield. If you plan on staying near or in the Pittsfield area, consider one of the following places to stay for a week or more. Weekly stays are a great way to unwind and unplug. These places to stay have all been rated as one of the Top Places to Stay in Pittsfield:

How many vacation rentals have private pools in Pittsfield?

We have found 2 places to stay that feature a private swimming pool in or near Pittsfield. Some of the best places to stay that feature or have access to a swimming pool are:

Which vacation homes in Pittsfield are best for families?

If you are looking for a place to stay that is family-friendly in Pittsfield, check out one of the following places as all are highly-rated options and have received excellent reviews for families or groups staying in Pittsfield:

How many Varoom vacation rentals are available in Pittsfield?

Varoom updates its properties nightly to bring you a great selection of places to stay. Currently, the total number of properties listed by Varoom in 2026 is over 106 in the Pittsfield area, and still growing every day. When we combine listings from multiple websites and travel providers, Varoom can provide you with a diverse amount of choice of the best places to stay in Pittsfield. 


People Also Ask

There are 106 Pittsfield, MA Vacation Rentals

Recently Booked Vacation Rentals in Pittsfield