Choose from 1,477 vacation rentals located in Berkshires, Massachusetts. Top filters in Berkshires include Internet / Wifi, Kitchen / Kitchenette, and Parking. Prices range from $49 to $9,540 per night. Our most popular vacation rental types near Berkshires are Condo and Hotel.

Top vacation rentals in Berkshires

Property view
4.6
Outstanding(399 Reviews)
Bed and Breakfast
 in Lenox
The Cornell Inn
Garden · Kitchen / Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to 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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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 Berkshires for House, for $175 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property view
4.0
Good(113 Reviews)
Hotel
 in Williamstown
3star
Fairfield Inn & Suites by Marriott Williamstown
Pool · Kitchen / Kitchenette · Air conditioner

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

$$$$
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Room
4.9
Outstanding(207 Reviews)
House
 in Lee
The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History
20 guests · 6 bedrooms · 5 baths
Garden · Kitchen / Kitchenette · Air conditioner

Nestled in 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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Search by amenity

Vacation rentals with internet & wifi in Berkshires

Back of house with deck and fire pit
5.0
Outstanding(147 Reviews)
House
 in Peru
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
6 guests · 3 bedrooms · 2 baths
Ski in / Ski out · Garden · Pets allowed

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Berkshires, at $218 per night for your next great vacation.

$$$$
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Picture yourself, lakefront, on your dock on lovely 150 acre private lake.
4.9
Outstanding(150 Reviews)
House
 in Sheffield
“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
4 guests · 2 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

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

$$$$
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Exterior
4.7
Outstanding(179 Reviews)
House
 in Becket
Peace and quiet on the lake
6 guests · 2 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

Experience vacation in Berkshires with our House, Peace and quiet on the lake. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property view
4.0
Good(471 Reviews)
Hotel
 in Lee
2star
Quality Inn
Air conditioner · Internet / Wifi · Parking

This Hotel for $50 in Berkshires, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Berkshires

Berkshires travel guide

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

Vacation rentals in Berkshires have a price range between $49-$9,540. The average price for rentals in Berkshires is $270 per night.

What are the most popular vacation rental amenities in Berkshires?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • Parking

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