Photo by Photo courtesy of Berkshire Visitors Bureau

The Berkshires holiday homes

We found 1,516 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – The Berkshires

Showing deals for:30 Oct - 6 Nov

Image gallery for Sunny Chalet: woods of Ashfield

Interior
9.6 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)

Sunny Chalet: woods of Ashfield

Ashfield

16% off
Price is NZ$4,884
for 7 nights, 1 chalet
NZ$698 per night
includes taxes & fees
Sunny Chalet: woods of Ashfield

Find spaces that suit your style

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    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit The Berkshires

  • Scenic Nature Reserves: Explore a variety of outdoor escapes, from tranquil lakes to lush mountain trails perfect for hiking and picnics.
  • Rich Cultural Heritage: Immerse yourself in history with visits to local museums and historic houses reflecting the region’s past.
  • Family-Friendly Adventures: Enjoy activities suitable for all ages, including nature walks and interactive exhibits.
  • Romantic Escapes: Discover serene spots ideal for couples seeking a peaceful retreat amid stunning landscapes.
  • Active Outdoor Experiences: Engage in adventure sports and leisurely strolls through picturesque Berkshire County.

Top attractions near The Berkshires

The Berkshires in Massachusetts offer a blend of outdoor adventures, cultural experiences, and stunning scenery. Visitors can explore historic houses, nature reserves, and lakes, making it ideal for those seeking an active yet relaxing holiday. The region also features local attractions such as museums and adventure experiences that capture the spirit of the Berkshires, ensuring an engaging and memorable visit.

  • National Shrine of the Divine Mercy: A culturally rich shrine set 19km from The Berkshires, offering a serene spiritual retreat with unique architectural beauty.
  • The Mount: A historic house 23km from The Berkshires, renowned for its cultural ambience and storied past, perfect for history enthusiasts.
  • Bidwell House Museum: A historic house 6km from The Berkshires, showcasing a wealth of local history and culture in an intimate setting.

Things to do recommended for couples

Discover the magic of The Berkshires with leisurely strolls along scenic trails, cosy wine tasting sessions, and intimate candlelit dinners. Enjoy a memorable escape with your partner in this charming corner of Massachusetts.

Things to do recommended for families

Families can explore the Berkshire Museum's interactive exhibits and stroll through the scenic trails of the Berkshire Botanical Garden, offering an immersive local experience for children and adults alike.

Things to do recommended for groups

Experience the thrill of ziplining at Catamount Aerial Adventure Park, located 27km from The Berkshires, perfect for group adventures and outdoor fun.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around The Berkshires

When planning your trip, whether you're travelling with a group, as a family, bringing your pets, or looking for extended stays, be sure to choose the right filters to suit your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to The Berkshires with a group: Consider how many bedrooms you require along with extras like a full kitchen or an outdoor area for group get-togethers. Luckily, you can use filters on Vrbo to find all these features and more.
  • Traveling to The Berkshires with young kids: Travelling with young kids can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to The Berkshires: For many, a family holiday isn’t complete without their furry companion. If that sounds like you, take a look at Vrbo properties that welcome pets. Most pet-friendly places offer feeding bowls and beds to ensure everyone feels right at home.
  • Planning for a long term stay visiting The Berkshires: If you're searching for holiday rentals with great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near The Berkshires

Discover the enchanting Berkshires in Massachusetts, where breathtaking landscapes and vibrant history create the perfect backdrop for outdoor adventures. Wander through scenic Berkshire County, explore beautiful Berkshire Mountains, and immerse yourself in a rich tapestry of family-friendly, historic, and romantic vibes. This region offers a unique blend of natural splendour and cultural heritage for travellers seeking both relaxation and excitement.

  • Great Barrington: Nestled 18km from The Berkshires, Great Barrington offers an exciting mix of ski and adventure activities. The city is a hub for winter sports enthusiasts, with plenty of ski fields and resorts to explore. Beyond the slopes, visitors can enjoy the natural beauty of nearby lakes and mountains, as well as the vast expanses of national state parks, making it an ideal spot for sports and outdoor escapades.
  • Stockbridge: Located 19km from The Berkshires, Stockbridge exudes a quaint, culture-rich charm. It is a perfect destination for those seeking a romantic and entertainment-themed getaway, with access to music concerts, theatres and even a ski field. The area is highlighted by picturesque lakes, historic monuments and revered places of worship, offering travellers a blend of art, history and scenic beauty.
  • Monterey: A mere 5km from The Berkshires, Monterey is celebrated for its outdoor and scenic appeal. This city invites visitors to explore its ski fields and resorts, promising a mix of outdoor adventure and a romantic ambience. The local attractions, including lakes, mountains and parks, make Monterey a delightful destination for those who appreciate nature's splendor and a relaxed pace of life.

Best time to go to The Berkshires

If you're planning a trip to The Berkshires, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January22.8°F (-5.1°C)Light RainMostly CloudySlightly Low
February24.6°F (-4.1°C)Light RainMostly CloudyAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverage
April44.2°F (6.8°C)Light RainMostly CloudyAverage
May56.3°F (13.5°C)Light RainMostly SunnyAverage
June64.0°F (17.8°C)Light RainMostly SunnySlightly High
July70.3°F (21.3°C)Light RainMostly SunnySlightly High
August68.4°F (20.2°C)Light RainMostly SunnySlightly High
September61.3°F (16.3°C)Light RainMostly SunnyAverage
October50.0°F (10.0°C)Light RainMostly SunnyAverage
November37.8°F (3.2°C)Light RainMostly SunnySlightly Low
December29.5°F (-1.4°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is simple

Are you keen to save on your next adventure? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental. We’re here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, manage your existing arrangements, or review your bookings. Your saved or booked properties are thoughtfully categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Why people love visiting captivating The Berkshires

Take a holiday to The Berkshires and enjoy the area's entertainment, museums and opera. Well known for its baseball games, hiking and skiing, this scenic city won't disappoint. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around The Berkshires

Are you hoping to find attractions to visit during your stay? You'll be sure to enjoy The Berkshires for its hiking and skiing. Venture out of your cosy holiday rental and experience everything that makes The Berkshires a fun spot to go on holiday. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Otis Ridge (3.2 mi / 5.1 km)
  • Umpachene Falls Park (8 mi / 12.9 km)
  • Ski Butternut (8.8 mi / 14.2 km)
  • Blandford Ski Area (12.1 mi / 19.5 km)
  • Wyndhurst Golf & Club (13.6 mi / 21.9 km)
  • Hotchkiss Mobile Studio (16.1 mi / 25.9 km)

Exploring the natural features in The Berkshires

Whether you're an active traveller or just want to spend some time taking in the scenery, The Berkshires is a great place to get out in nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Ashintully Gardens (3.6 mi / 5.8 km)
  • Otis Reservoir (5.7 mi / 9.1 km)
  • Pyramid Lake (6.4 mi / 10.2 km)
  • Lake Buel (6.5 mi / 10.4 km)
  • Umpachene Falls Park (8 mi / 12.9 km)
  • Goose Pond Reservation (8.2 mi / 13.3 km)

Transport options to and around The Berkshires

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 19.3 mi (31 km) from the city centre.

If you're travelling by train, make your way to Pittsfield Station or Pittsfield Intermodal Transportation Center and explore the city from there.

Frequently asked questions

What is the best area to stay in The Berkshires when booking a holiday home?
One of the most popular areas to find a The Berkshires holiday home is Hancock. When you lock in your Bookabach holiday property, you'll enjoy having the whole place to yourself. So you don't have to share it with anyone apart from your group.
What is the most popular type of holiday home accommodation in The Berkshires?
The most sought-after types of holiday homes in The Berkshires are houses. After something a little different? Bookabach has a variety of options to match our guests' needs, so you'll see holiday properties in all sizes, and for all budgets. The perfect home away from home is waiting for you — get yours today.
How much does it cost to rent a holiday home in The Berkshires?
A number of things can affect what you'll pay for your holiday home in The Berkshires, such as the length of stay, type of property and season. Still, all of our holiday homes have one thing in common — incredible value. Just add your travel dates to find your ideal match.
How much does it cost to rent a beach house in The Berkshires?
The average price for a holiday home close to the beach in The Berkshires depends on when you're visiting the area and the size and style of property you want. Find prices easily on Bookabach by entering your preferred travel dates. Then use the filters to select the number of bedrooms and amenities that you prefer, like a pool, air conditioning and WiFi.
What are popular home amenities in The Berkshires?
When it comes to home amenities that guests search for in The Berkshires, a microwave oven, a stovetop and a fridge are the most popular. With Bookabach holiday homes, you'll find options to fit your style and taste, whether you're travelling with family members, friends or even pets.
Are there large group holiday homes in The Berkshires?
With 94 properties that can sleep 10 guests or more in The Berkshires, there's no need to leave anyone off your guest list. From fun family get-togethers to events like birthday parties and weddings, Bookabach will help you find a large group home that fits the occasion.
What are the top attractions for families in The Berkshires?
There are lots of fun things to do and see with the family in The Berkshires, such as:

  • Bousquet Ski Area
  • Ski Butternut
  • Jiminy Peak Mountain Resort

Can I find two-bedroom holiday homes in The Berkshires?
Take your pick of 144 two-bedroom homes in The Berkshires. Give the kids the second room or fill it with a couple of your best buddies. There's a spot for whoever's lucky enough to come along for the ride.
Are there holiday homes with WiFi in The Berkshires?
Whether you'd like to keep up with the headlines, reply to emails or post a pic to social media, there are 205 holiday homes with WiFi in The Berkshires. Check the "WiFi" box when searching on Bookabach and stay connected on your getaway.
How old do you have to be to rent a holiday home in The Berkshires?
You'll need to check with the Berkshires holiday home you'd like on Bookabach as age restrictions differ. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in The Berkshires for?
The length of time you can book a holiday home in The Berkshires depends on the property. Just enter your desired dates to display a list of options offering extended stays. With plenty of features such as laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get a perfect place to call your home away from home in The Berkshires.

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