104+ Luxury Vacation Rentals & Cabins in Pittsfield |
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Pittsfield Cabin Rentals

About Pittsfield Vacation Rentals

There are more than 104 incredible getaway rentals that are available in Pittsfield. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.com and uncover great stays in Pittsfield.

Cabinns.com features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. 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 Cabinns.com in Pittsfield, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.com vacation rentals, resorts, and Airbnb-style properties in Pittsfield. Places to stay near Pittsfield are 1168.68 ft² on average, with prices averaging US $386 a night.

Cabinns.com helps you find the ideal holiday rental to create a lifetime of travel memories in Pittsfield. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Pittsfield

Type Count
Vacation Homes 61
Holiday Apartments 11
Cottages 4
Cabin Rentals 3
Others 1

Use these Quick Filters to Find a Vacation Rental in Pittsfield

★ Pro Tip: Cabinns.com is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Pittsfield with Cabinns.com.

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

Activities Pittsfield Guest Reviews Local Attractions

Cabins Provides a Large Selection of Cabins and Vacation Rentals in and Near Pittsfield. Discover Top Attractions For Your Next Outdoor Adventure.


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

Find Nearby Cabin Rentals in these Cities & Neighborhoods


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

Complexes around Pittsfield, MA


Hilton Garden Inn Pittsfield 3 Properties

Frequently Asked Questions About Pittsfield?

What are the top cabins, lake houses & summer homes in Pittsfield?

We provide an array of great vacation destinations in Pittsfield. If you are looking to stay in or around the Pittsfield area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Pittsfield:

How many cabin rentals and resorts have private pools in Pittsfield?

We have 1 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Pittsfield. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Pittsfield is best for families?

Searching for a family-friendly cabin in Pittsfield? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Pittsfield?

Cabinns.com offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.com in 2025 is over 104 in the Pittsfield area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.com can provide you with a diverse amount of choices of the best luxury stays in Pittsfield.


People Also Ask

There are 16 hotels in Pittsfield 2 resorts, and 75 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Pittsfield