Choose from 1,542 vacation rentals located in The Berkshires, Massachusetts. Top filters in The Berkshires include Internet / Wifi, Kitchen or Kitchenette, and Air conditioner. Prices range from $76 to $21,221 per night. Our most popular vacation rental types near The Berkshires are Apartment and Hotel.

Top vacation rentals in The Berkshires

Hot Tub
4.3
Excellent(1,491 Reviews)
Vacation Village in the Berkshires
Resort
 in Hancock
1 sofa bed, 1 queen bed
Garden · Pool · Kitchen or Kitchenette

Nestled in The Berkshires, this Resort is perfect for your next vacation. Enjoy Vacation Village in the Berkshires's top-rated amenities, including Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$
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Property building, On site
3.5
Average(198 Reviews)
Travelodge by Wyndham Great Barrington Berkshires
Motel
 in Great Barrington
2 full beds
Pool · Kitchen or Kitchenette · Air conditioner

Experience vacation in The Berkshires with our Motel, Travelodge by Wyndham Great Barrington Berkshires. Enjoy amenities such as Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Facade/entrance
4.6
Outstanding(524 Reviews)
The Cornell Inn
Bed and Breakfast
 in Lenox
1 queen bed
Garden · Kitchen or Kitchenette · Air conditioner

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

$$$$
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Interior
5.0
Outstanding(221 Reviews)
The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History
House
 in Lee
20 guests · 6 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner

Nestled in The Berkshires, this House is perfect for your next vacation. Enjoy The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Explore vacation rentals with the most popular amenities in The Berkshires

Vacation rentals with internet & wifi in The Berkshires

Exterior
4.7
Outstanding(205 Reviews)
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Cabin
 in Becket
4 guests · 2 bedrooms · 1 bath
Garden · Pets allowed · Kitchen or Kitchenette

Enjoy the best of The Berkshires in our Cabin, Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating. A stunning property with amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Property grounds
5.0
Outstanding(160 Reviews)
“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
House
 in Sheffield
4 guests · 5 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette

Indulge in a peaceful retreat at “Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway, our elegant House in The Berkshires. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Property building
3.4
Average(335 Reviews)
Howard Johnson by Wyndham Lenox
Hotel
 in Lenox
2star
1 full bed
Garden · Pool · Kitchen or Kitchenette

Nestled in The Berkshires, 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 or Kitchenette, and more.

$$$$
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Property building
4.2
Excellent(914 Reviews)
The Yankee, Trademark Collection by Wyndham
Hotel
 in Lenox
3star
1 king bed, 1 sofa bed
Pool · Kitchen or Kitchenette · Air conditioner
Most favorited

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

$$$$
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The Berkshires

The Berkshires travel guide

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

Frequently asked questions

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

Before visiting Berkshires, MA, it's important to know a few things:

  • Berkshires is in the western part of the state and is known for its outdoor activities, such as skiing and hiking.
  • The Berkshires have a variety of restaurants, cafes, and shops.
  • The area is home to many cultural attractions, including museums, galleries, and theaters.

It's also important to plan ahead and be aware of the weather, as it can be unpredictable. Make sure to bring the proper clothing and gear for the activities you plan to do.

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

Berkshires, MA is a great place to visit, with a variety of tourist attractions to explore. Here are some of the top must-see tourist attractions:

  • The Norman Rockwell Museum
  • The Mount Greylock State Reservation
  • The Berkshire Museum
  • The Clark Art Institute

All these attractions are great for people of all ages, and offer a variety of activities and experiences. Whether you're interested in art, culture, or nature, Berkshires, MA has something for everyone.

How can I get around in Berkshires, MA?

You can get around in Berkshires, MA using the following methods:

  • By car
  • By bus
  • By bike

Berkshire Regional Transit Authority (BRTA) provides bus service to many towns in the Berkshires. The area is also well-suited for biking, with plenty of bike lanes and trails. Additionally, there are several car rental options in the area.

Where can I find affordable accommodation in Berkshires, MA?

Berkshires, MA offers a variety of affordable accommodation options for travelers. Here are a few to consider:

  • Berkshire Inn – Located in Pittsfield, this hotel offers a range of amenities and a great location near local attractions.
  • Berkshire Vacation Rentals – Enjoy the comforts of home with a short-term rental in the Berkshires.
  • Berkshire Bed & Breakfast – Experience a cozy stay in a local B&B, with a variety of amenities and home-cooked breakfasts.
  • Camping in the Berkshires – Enjoy the great outdoors with a camping trip to the Berkshires.

What is the culture like in Berkshires, MA?

The culture in Berkshires, MA is truly unique and vibrant. From the stunning natural beauty of the Appalachian Mountains to the rich cultural heritage, there is something for everyone. Here are five aspects of the culture in Berkshires, MA:

  • Outdoor Recreation: The Berkshires are home to many outdoor activities such as hiking, biking, fishing, and camping.
  • Arts and Music: The Berkshires are known for their numerous art galleries, music venues, and performing arts centers.
  • Local Cuisine: The Berkshires offer a variety of locally-sourced food and drink, including farm-to-table restaurants and craft breweries.
  • History: The Berkshires are home to many historical sites, including the Norman Rockwell Museum and the Hancock Shaker Village.
  • Community: The Berkshires have a strong sense of community, with many festivals and events that bring people together.

Is Berkshires, MA safe to travel to?

Berkshires, MA is generally safe to travel to. Here are a few tips to ensure a safe and enjoyable trip:

  • Familiarize yourself with your route ahead of time.
  • Be aware of your surroundings at all times.
  • Keep your valuables in a secure location.

Following these tips can help to ensure that your trip to Berkshires, MA is safe and enjoyable.

What are the popular shopping destinations in Berkshires, MA?

Berkshires, MA is a popular shopping destination, with a variety of unique stores to choose from. Here are some of the top spots to check out:

  • The Shops at the Interlaken: a collection of boutiques, art galleries, and specialty stores.
  • Berkshire Mall: a shopping center with over 50 stores, including Macy's and JCPenney.
  • Downtown Pittsfield: a vibrant downtown area with a variety of independent shops and restaurants.

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

The best neighborhoods to visit in Berkshires, MA are:

  • Lenox
  • Great Barrington
  • Stockbridge

Each of these charming towns offer a variety of activities from outdoor recreation and local shopping to art galleries and museums. Visitors can explore the area's natural beauty, try some of the local restaurants, and visit some of the historic sites.

Where is Berkshires, MA?

Berkshires, MA is located in western Massachusetts. It is a popular summer destination known for its beautiful mountains, lakes, and rivers. It is home to numerous cultural attractions such as the Norman Rockwell Museum, the Clark Art Institute, and the Williamstown Theatre Festival.

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

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

  • Fully-equipped kitchens
  • Spacious outdoor areas
  • High-speed internet access
  • In-unit laundry facilities
  • Private hot tubs

These amenities provide visitors with the convenience and comfort of home while on vacation, making Berkshires, MA a popular destination for travelers and vacationers alike.

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

The Berkshires, located in western Massachusetts, is a popular destination for outdoor recreation, arts, and entertainment. Here are some of the top things to do in the Berkshires:

  • Visit the Berkshire Botanical Garden in Stockbridge.
  • Explore the Norman Rockwell Museum in Stockbridge.
  • Hike the Appalachian Trail in the Berkshires.
  • Catch a performance at Tanglewood music center.

What is the price range for rentals in The Berkshires?

Vacation rentals in The Berkshires have a price range between $76-$21,221. The average price for rentals in The Berkshires is $312 per night.

What are the most popular vacation rental amenities in The Berkshires?

  • Internet / Wifi
  • Kitchen or Kitchenette
  • Air conditioner

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