Choose from 81 vacation rentals located in Pittsfield, Massachusetts. Top filters in Pittsfield include Internet / Wifi, Parking, and Kitchen / Kitchenette. Prices range from $56 to $1,700 per night. Our most popular vacation rental types near Pittsfield are Condo and Hotel.

Top vacation rentals in Pittsfield

Great Room
4.8
Outstanding(126 Reviews)
House
 in Pittsfield
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
25 guests · 8 bedrooms · 3 baths
Garden · Pets allowed · Kitchen / Kitchenette

This attractive House in Pittsfield, $395 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Property view
4.2
Excellent(948 Reviews)
Hotel
 in Lenox
3star
The Yankee, Trademark Collection by Wyndham
Pool · Kitchen / Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Pittsfield? This Hotel offers a comfort and style with top-notch amenities, including Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$
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3.9
Good(245 Reviews)
Hotel
 in Pittsfield
3star
Best Western Plus Berkshire Hills Inn & Suites
Garden · Kitchen / Kitchenette · Air conditioner

The best choice in Pittsfield for Hotel, for $92 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Property view
4.8
Outstanding(196 Reviews)
House
 in Lanesborough
Berkshire Village Carriage House - Super Private!!
2 guests · 1 bedroom · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

The best choice in Pittsfield for House, for $150 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Vacation rentals with internet & wifi in Pittsfield

Our private dock on Richmond Pond has a spectacular view, especially at sunset.
4.8
Outstanding(85 Reviews)
House
 in Pittsfield
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
7 guests · 3 bedrooms · 3 baths
Garden · Pool · Pets allowed

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Pittsfield, at $262 per night for your next great vacation.

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Drone photo prior to replacing the dock
5.0
Outstanding(87 Reviews)
House
 in Pittsfield
Modern 4 bedroom lakefront house in The Berkshires.
8 guests · 4 bedrooms · 4 baths
Garden · Kitchen / Kitchenette · Air conditioner

Looking for a House in Pittsfield, this House for $525 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

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The living is easy anytime of the year  in the Berkshires
4.8
Outstanding(79 Reviews)
House
 in Pittsfield
Featured in a Home & Garden TV Special 30 South Mountain Road
4 guests · 2 bedrooms · 1 bath
Garden · Pets allowed · Kitchen / Kitchenette

This attractive House in Pittsfield, $285 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property view
3.4
Average(348 Reviews)
Hotel
 in Lenox
2star
Howard Johnson by Wyndham Lenox
Garden · Pool · Kitchen / Kitchenette

Nestled in Pittsfield, this Hotel is perfect for your next vacation. Enjoy Howard Johnson by Wyndham Lenox's top-rated amenities, including Air conditioner, Internet / Wifi and Kitchen / Kitchenette, and more.

$$$$
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Pittsfield

Pittsfield travel guide

Let us help you plan your perfect Pittsfield vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Pittsfield, and more.

Frequently asked questions

What do I need to know before visiting Pittsfield, MA?

Before you visit Pittsfield, MA, you should know a few things.

  • The city has a population of around 44,000 people.
  • The climate is generally cold in the winter and warm in the summer.
  • It is a popular tourist destination for its outdoor activities, art and culture.

The city is home to a variety of attractions, including the Berkshire Museum, the Colonial Theatre, and the Berkshire Athenaeum. There are also plenty of outdoor activities, such as golf, fishing, and hiking.

What are the must-visit tourist attractions in Pittsfield, MA?

Pittsfield, MA is a great place to visit, with plenty of attractions to explore. Here are some of the must-visit tourist attractions in Pittsfield:

  • Berkshire Museum
  • Shaker Museum and Library
  • The Colonial Theatre
  • The Mount
Visiting Pittsfield is an amazing experience, with lots to explore and discover. Whether it's visiting the Berkshire Museum, the Shaker Museum and Library, the Colonial Theatre, or The Mount, Pittsfield has something to offer for everyone.

How can I get around in Pittsfield, MA?

There are several ways to get around Pittsfield, MA:

  • Driving - Pittsfield is served by several major roads and highways, such as the Massachusetts Turnpike, Route 8, and Route 9.
  • Public Transit - The Berkshire Regional Transit Authority (BRTA) offers bus service throughout Pittsfield and the surrounding area.
  • Biking - Pittsfield has several bike paths and trails, as well as a bike-share program.

Where can I find affordable accommodation in Pittsfield, MA?

Pittsfield, MA offers a variety of affordable accommodation options for visitors. Here are some of the top choices:

  • The Pittsfield Inn: A cozy, family-run inn with free breakfast and Wi-Fi.
  • The Comfort Inn: Offering great value for money, with a fitness center and free Wi-Fi.
  • The Red Roof Inn: A budget-friendly hotel with free parking and a continental breakfast.
  • The Hampton Inn: A modern hotel with a pool and free Wi-Fi.

No matter what your budget and needs are, Pittsfield, MA has something for everyone!

What is the culture like in Pittsfield, MA?

Pittsfield, MA is a small city located in Berkshire County. It is a great place to live, with a rich cultural life and a diverse population. Here are five things to know about the culture in Pittsfield:

  • The city is home to a variety of arts and cultural organizations, including the Berkshire Theatre Group, the Colonial Theatre, and the Berkshire Museum.
  • Pittsfield is known for its vibrant music scene, with a variety of venues hosting live music performances.
  • The city is also home to several museums, such as the Berkshire Museum and the Herman Melville House.
  • The city is also home to a variety of festivals and events throughout the year, such as the Pittsfield CityJazz Festival and the Pittsfield Parade.
  • The city also hosts several annual events, such as the Pittsfield City Fair and the Pittsfield CityFolk Festival.

Is Pittsfield, MA safe to travel to?

Pittsfield, MA is generally a safe place to travel to. Here are a few tips to help ensure your safety:

  • Be aware of your surroundings.
  • Do not carry large amounts of cash.
  • Avoid walking alone at night.

What are the popular shopping destinations in Pittsfield, MA?

Popular shopping destinations in Pittsfield, MA include:

  • Berkshire Mall
  • Downtown Pittsfield
  • The Shops at Five

Berkshire Mall is the largest shopping center in Pittsfield, with over 60 stores including department stores, restaurants, and entertainment. Downtown Pittsfield offers a variety of unique boutiques, restaurants, and galleries. The Shops at Five is a shopping center located near the center of town, featuring a variety of shops and restaurants.

What are the best neighborhoods to visit in Pittsfield, MA?

The best neighborhoods to visit in Pittsfield, MA are:

  • Downtown
  • Morningside
  • Allendale

Downtown is the city's bustling center, with great restaurants, shops, and cultural attractions. Morningside is a vibrant, up-and-coming neighborhood with a mix of old and new. Allendale is a quiet residential area with a beautiful park and plenty of outdoor activities.

Where is Pittsfield, MA?

Pittsfield, MA is a city in Berkshire County, located in the westernmost part of Massachusetts. It is the largest city in the county with a population of nearly 45,000, and is the principal city of the Pittsfield, MA Metropolitan Statistical Area. Pittsfield is located in the Berkshire Hills and is home to a variety of attractions, including theaters, art galleries, and a vibrant downtown.

What are the most popular vacation rental amenities in Pittsfield, MA?

The most popular vacation rental amenities in Pittsfield, MA include:

  • Fully-equipped kitchens
  • Free Wi-Fi
  • On-site laundry facilities
  • Air conditioning
  • Spacious outdoor areas

These amenities provide vacationers with the comfort and convenience of home while they explore the area. Many vacation rental properties in Pittsfield also offer additional features such as swimming pools, hot tubs, and BBQ areas to further enhance their stay.

What are the top things to do in Pittsfield, MA?

Pittsfield, MA is a great destination for a variety of activities. Here are some of the top things to do in the area:

  • Visit the Berkshire Museum and explore its interactive exhibits.
  • Take a stroll through the Hancock Shaker Village and explore its history.
  • Go on a hike at the Pittsfield State Forest.
  • Enjoy the local cuisine at one of the many restaurants in the area.

What is the price range for rentals in Pittsfield?

Vacation rentals in Pittsfield have a price range between $56-$1,700. The average price for rentals in Pittsfield is $199 per night.

What are the most popular vacation rental amenities in Pittsfield?

  • Internet / Wifi
  • Parking
  • Kitchen / Kitchenette

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