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Home/United States/Massachusetts/Stockbridge

Vacation Rentals in Stockbridge, MA

Search the perfect vacation rental

Property type

Popular amenities

Choose from 169 vacation rentals located in Stockbridge, Massachusetts. Top filters in Stockbridge include Non-smoking, Family friendly, and No pets allowed. Prices range from $67 to $1,809 per night. Our most popular vacation rental types near Stockbridge are Hotel and RV.

Top vacation rentals in Stockbridge

Breakfast Nook - wake up to the best sunshine ever!
9.8 / 10
Outstanding(146 Ratings)
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
House
 in Stockbridge
8 guests · 4 bedrooms · 3 baths

Experience the best of Stockbridge with this House available for $406. This property is equipped with amenities including ;, and more.

$$$$
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Property building, Property logo or sign, Street view
8.1 / 10
Excellent(304 Ratings)
The Red Lion Inn
Hotel
 in Stockbridge
4star
2 guests · 1 bedroom · 1 bath

Enjoy the best of Stockbridge in our Hotel, The Red Lion Inn. A stunning property with amenities including ;, and more.

$$$$
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Property building, Facade/entrance, Spring, Day, Internal: Not applicable to any particular room
9.3 / 10
Outstanding(18 Ratings)
Stockbridge Country Inn
Bed and Breakfast
 in Stockbridge
4star
2 guests · 1 bedroom · 1 bath

This Bed and Breakfast in Stockbridge, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Property view
8.8 / 10
Excellent(3 Ratings)
The Inn at Stockbridge
Bed and Breakfast
 in Stockbridge
4star
2 guests · 1 bedroom · 1 bath

Experience the best of Stockbridge with this Bed and Breakfast available for $1,014. This property is equipped with amenities including ;, and more.

$$$$
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Search by amenity

Explore vacation rentals with the most popular amenities in Stockbridge

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Stockbridge

Stockbridge travel guide

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

Explore near Stockbridge

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Frequently asked questions

What is the price range for rentals in Stockbridge?

Vacation rentals in Stockbridge have a price range between $67-$1,809. The average price for rentals in Stockbridge is $400 per night.

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

Stockbridge, MA is a great destination for a weekend getaway. Here are some of the top things to do in the area:

  • Visit the Norman Rockwell Museum
  • Explore the outdoor beauty of the Berkshires
  • Shop at the Red Lion Inn
  • Take a tour of the Chesterwood Estate

No matter what you're looking for, Stockbridge has something to offer for everyone. Enjoy the beauty of the Berkshires and explore the history of the area.

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

The most popular vacation rental amenities in Stockbridge, MA are:

  • A fully equipped kitchen
  • Comfortable beds with quality linens
  • High speed internet access
  • A private outdoor space with seating
  • Air conditioning

These amenities provide guests with a comfortable and convenient stay, allowing them to cook their own meals, relax in a peaceful outdoor space, and stay connected with the world. Air conditioning is also a must-have for those hot summer days.

Where is Stockbridge, MA?

Stockbridge, MA is located in western Massachusetts in the Berkshire Mountains. It is a small town, with a population of 1,947 as of the 2010 census. It is known for its natural beauty, and is home to the popular tourist attraction, the Norman Rockwell Museum.

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

The best neighborhoods to visit in Stockbridge, MA are:

  • Main Street – home to the iconic Red Lion Inn and the Norman Rockwell Museum
  • Housatonic Street – the town’s main shopping district
  • South Street – a historic residential area with a variety of Victorian-style homes

What are the popular shopping destinations in Stockbridge, MA?

Stockbridge, MA is a popular shopping destination with many unique stores and boutiques. Here are some of the popular spots:

  • The Red Lion Inn Shops
  • Stockbridge Main Street at Christmas
  • Norman Rockwell Museum Gift Shop
  • The Yankee Candle Village

Is Stockbridge, MA safe to travel to?

Stockbridge, MA is a safe place to travel to. Here are a few reasons why:

  • Low crime rate
  • Friendly residents
  • Well-maintained roads and infrastructure

Overall, Stockbridge is a safe and enjoyable place to visit.

What is the culture like in Stockbridge, MA?

Stockbridge, MA is a small town in the Berkshire Mountains of western Massachusetts. It has a rich cultural history with a variety of attractions and activities for visitors and locals alike. Here are five aspects of the culture in Stockbridge:

  • The Norman Rockwell Museum features the work of the famous American artist.
  • The Berkshire Theatre Festival is a professional summer theatre that produces a variety of musicals and plays.
  • The town hosts a number of traditional events such as the Great Barrington Fair and the Stockbridge Summer Festival.
  • The town is home to a number of art galleries, antique shops, and specialty stores.
  • The town is also home to the Stockbridge Library, Museum and Archives, which houses a collection of artifacts, books, and documents related to the history of the town.

Where can I find affordable accommodation in Stockbridge, MA?

Stockbridge, MA offers a variety of accommodation options that are both affordable and convenient. Here are a few of the top choices:

  • The Red Lion Inn: A historic inn located in the heart of Stockbridge, offering comfortable rooms with modern amenities.
  • The Inn at Stockbridge: A charming inn located in the center of town, featuring cozy rooms and a delicious breakfast.
  • The Stockbridge Motel: A budget-friendly option, offering simple but comfortable rooms with all the basics.
  • The Stockbridge Bed & Breakfast: An intimate B&B located in a beautiful Victorian home, offering a unique and comfortable stay.

How can I get around in Stockbridge, MA?

You can get around Stockbridge, MA in a variety of ways:

  • Drive - there are many roads throughout the town.
  • Walk - the town is quite pedestrian-friendly.
  • Bike - there are plenty of trails and bike lanes.

You can also use public transportation to get around the town, including bus, taxi, and rideshare services.

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

Stockbridge, MA is a charming New England town with plenty of attractions to explore. Here are some of the must-visit tourist attractions in Stockbridge:

  • Naumkeag: A Gilded Age Mansion and Gardens
  • Berkshire Botanical Garden
  • Hancock Shaker Village
  • Norman Rockwell Museum

Visitors to Stockbridge can also explore the local shops, restaurants, and galleries. There's plenty to do in this small town for a great day trip or weekend getaway.

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

Before visiting Stockbridge, MA, it is important to know that the town is located in the beautiful Berkshire Mountains, and is home to the Norman Rockwell Museum, which houses the largest collection of Rockwell's work. Additionally, Stockbridge is home to several outdoor activities and attractions, making it a great destination for both tourists and locals alike.

  • Stockbridge is located in the Berkshire Mountains
  • The Norman Rockwell Museum is located in Stockbridge
  • Stockbridge is home to several outdoor activities and attractions

What are the most popular vacation rental amenities in Stockbridge?

  • Non-smoking
  • Family friendly
  • No pets allowed