Choose from 45 vacation rentals located in Pittsfield, Vermont. Top filters in Pittsfield include Internet / Wifi, Kitchen or Kitchenette, and Parking. Prices range from $71 to $2,843 per night. Our most popular vacation rental types near Pittsfield are Apartment and Hotel.

Top vacation rentals in Pittsfield

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Outdoor dining
4.8 / 5.0
Outstanding(61 Ratings)
Killington Skiers/Snowmobilers/MountainBikers Dream with Outdoor Jacuzzi + Wi-Fi
House
 in Stockbridge (Pittsfield)
8 guests · 3 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

This House in Pittsfield, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

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Property grounds
4.9 / 5.0
Outstanding(112 Ratings)
Killington area home - 4-seasons & hot tub. Sleeps 12+
House
 in Pittsfield
15 guests · 5 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette

This inviting House in Pittsfield can fit your needs for many types of vacations, at $440 per night.

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Property view
4.1 / 5.0
Excellent
Pittsfield Chalet
House
 in Pittsfield
Kitchen or Kitchenette · Internet / Wifi · Parking

This House for $102 in Pittsfield, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property building
4.4 / 5.0
Excellent(207 Ratings)
Clear River Inn and Tavern
Inn
 in Pittsfield
2 full beds
Pets allowed · Kitchen or Kitchenette · Air conditioner

Soak up the beauty of Pittsfield in our Inn, Clear River Inn and Tavern. With a range of amenities such as Air conditioner, Internet / Wifi and Laundry, you'll feel right at home.

$$$$
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Vacation rentals with internet & wifi in Pittsfield

Smart TV, fireplace, video games, DVD player
4.9 / 5.0
Outstanding(18 Ratings)
Four Season KILLINGTON Getaway!
House
 in Pittsfield
8 guests · 3 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Internet / Wifi

Looking to create some memories in Pittsfield? Look no further than our House, Four Season KILLINGTON Getaway!. Enjoy top-rated amenities including Fireplace, Internet / Wifi and Laundry, and more.

$$$$
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Property grounds
5.0 / 5.0
Outstanding(34 Ratings)
Beautiful Killington VT Ski & Mountain Bike 5 Season House
House
 in Pittsfield
12 guests · 5 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Internet / Wifi

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Pittsfield, at $710 per night for your next great vacation.

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Fridge, microwave, oven, stovetop
4.8 / 5.0
Outstanding(31 Ratings)
Killington ski house
House
 in Stockbridge
10 guests · 4 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Internet / Wifi

Nestled in Pittsfield, this House is perfect for your next vacation. Enjoy Killington ski house's top-rated amenities, including Dishwasher, Fireplace and Internet / Wifi, and more.

$$$$
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Interior
4.7 / 5.0
Outstanding(41 Ratings)
Killington Vermont Ski and Snowmobiling House
House
 in Pittsfield
14 guests · 6 bedrooms · 3 baths
Kitchen or Kitchenette · Internet / Wifi · Parking

Looking to create some memories in Pittsfield? Look no further than our House, Killington Vermont Ski and Snowmobiling House. Enjoy top-rated amenities including Dishwasher, Fireplace and Internet / Wifi, 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, VT?

Before visiting Pittsfield, VT, it is important to know the following:

  • Pittsfield is a small community located in central Vermont.
  • The town is known for its beautiful landscape and outdoor activities.
  • The area is home to a variety of shops, restaurants, and attractions.

The local attractions include the Pittsfield Town Hall, the Pittsfield Historical Society & Museum, and the Pittsfield Schoolhouse Museum. It is also important to be aware of the weather conditions before visiting the area, as the town can experience extreme temperatures during the winter months.

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

Pittsfield, VT is a charming small town with plenty of must-visit tourist attractions. Here are some of the top places to visit in Pittsfield:

  • The Pittsfield Historical Society
  • The Pittsfield Village Green
  • The Pittsfield General Store
  • The Pittsfield Town Hall

These are just a few of the many attractions that Pittsfield has to offer. Whether you're looking for a quiet afternoon stroll, or a fun-filled day of exploration, Pittsfield has something for everyone!

How can I get around in Pittsfield, VT?

You can get around in Pittsfield, VT by:

  • Driving
  • Biking
  • Walking

Where can I find affordable accommodation in Pittsfield, VT?

Pittsfield, VT offers a variety of affordable accommodation options for visitors. Here are a few to consider:

  • The Pittsfield Inn: This cozy inn offers affordable rooms and a convenient location in the heart of Pittsfield.
  • The Pittsfield Motel: Located just outside of town, this motel offers basic amenities and a budget-friendly rate.
  • The Pittsfield Lodge: This rustic lodge offers a unique experience and plenty of outdoor activities.
  • The Pittsfield Bed & Breakfast: This charming B&B offers a homey atmosphere and a great breakfast.

What is the culture like in Pittsfield, VT?

Pittsfield, VT is a small, rural town located in the heart of Vermont’s Green Mountains. The culture in Pittsfield is one of hard work, community, and an appreciation of nature. Here are five ways that the culture of Pittsfield is expressed:

  • A strong sense of community – the town’s residents are proud of their small-town roots, and are always willing to lend a helping hand when needed.
  • An appreciation for the outdoors – the town is surrounded by beautiful natural scenery, and its residents take full advantage of it, with hiking, biking, and fishing being popular activities.
  • A commitment to education – the town is home to an excellent school system, and the residents take great pride in their children’s educational success.
  • A respect for tradition – the town is filled with historic buildings and artifacts, and its residents take great care to preserve them.
  • A love of the arts – the town is home to a vibrant arts scene, with galleries, performances, and events taking place throughout the year.

Is Pittsfield, VT safe to travel to?

Pittsfield, VT is a safe destination to travel to. Here are a few reasons why:

  • Low crime rate
  • Friendly locals
  • Beautiful scenery

It's a great place to visit and explore!

What are the popular shopping destinations in Pittsfield, VT?

Pittsfield, VT offers a variety of shopping destinations for visitors to explore. Here are some of the most popular:

  • Pittsfield Trading Post
  • The Pittsfield Mall
  • The Pittsfield Shoppe
  • The Pittsfield Outlet

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

Pittsfield, VT is a great place to visit. Here are some of the best neighborhoods to explore:

  • Downtown: Home to the historic Pittsfield Opera House, this area is full of restaurants, shops, and entertainment.
  • Pittsfield Village: A quiet neighborhood with a beautiful view of the White Mountains.
  • The Shires: This area is known for its rolling hills and picturesque farms.

Where is Pittsfield, VT?

Pittsfield, VT is a small town located in the northwest corner of Vermont. It is situated in the Green Mountains of the state, and is known for its small-town charm and peaceful atmosphere. Visitors to Pittsfield can enjoy outdoor activities such as hiking and fishing, as well as a range of other activities, including visiting the local museum and taking in the views of the surrounding mountains.

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

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

  • Fully-equipped kitchens
  • Spacious living rooms
  • Cozy fireplaces
  • High-speed internet
  • Satellite or cable TV

These amenities make it easy for visitors to enjoy all the comforts of home while staying in Pittsfield, VT. Fully-equipped kitchens allow guests to cook their own meals, while spacious living rooms provide the perfect place to relax after a day of exploring. Cozy fireplaces are great for enjoying a cup of hot chocolate or roasting marshmallows. High-speed internet and satellite or cable TV provide entertainment options for all ages.

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

Pittsfield, VT is a small town with plenty of outdoor activities to enjoy. Here are some of the top things to do in Pittsfield:

  • Visit the Pittsfield Historical Society Museum
  • Go fishing at the White River
  • Take a hike on the Appalachian Trail
  • Explore the Pittsfield Town Forest

Whether you’re looking for a relaxing day outdoors or a fun day of sightseeing, Pittsfield has something for everyone.

What is the price range for rentals in Pittsfield?

Vacation rentals in Pittsfield have a price range between $71-$2,843. The average price for rentals in Pittsfield is $638 per night.

What are the most popular vacation rental amenities in Pittsfield?

  • Internet / Wifi
  • Kitchen or Kitchenette
  • Parking

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