Best apartment offers in Berkshire County, MA

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Berkshire County, MA apartments
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2082 Holiday apartments Berkshire County, MA

Best family friendly Berkshire County, MA Holiday Apartments and Self Catering Accommodations

Among the 2082 accommodations in Berkshire County, MA, here are the 4 best family friendly holiday apartments

2 Bed Berkshire Apt Minutes To Jiminy Peak Ski - Berkshire County, MA
9.3 41 reviews

2 Bed Berkshire Apt Minutes To Jiminy Peak Ski

apartment, East Nassau
This Stephentown, New York self-catering apartment is situated near the New York/Massachusetts border, an 8-minute drive from Jiminy Peak Ski Resort and close to Berkshire and Taconic Mountain attractions.
The 93-square-metre (1000 sq ft) property, a newly renovated unit within a historic 1860s building, features two bedrooms, one bathroom, a fully equipped kitchen, and sleeps up to four guests, offering a private entrance, parking, and a deck with a BBQ.
Dog/family Friendly A-frame! Walk To Lake/kayak Use In The Berkshires! - Berkshire County, MA
10 6 reviews

Dog/family Friendly A-frame! Walk To Lake/kayak Use In The Berkshires!

apartment, Becket
This pet-friendly apartment in Becket's Sherwood Forest neighbourhood is conveniently located approximately 3.2km from Pyramid Lake and 4.5km from the Jacob's Pillow Dance School.
The two-bedroom property, sleeping four, boasts a garden, spa, air conditioning, free Wi-Fi, and a well-equipped kitchen including a fridge and microwave, plus parking; nearby attractions include the Berkshire Theatre Festival and Ashintully Gardens.
The Lake House - Berkshire County, MA
10 45 reviews

The Lake House

apartment, Otis
This Sandisfield apartment, a two-bedroom lakeside property in Otis, Massachusetts, is a short walk from a lake.
The self-catering house sleeps six, features a fireplace, fire pit, parking for two vehicles, and is pet-friendly.
Lakefront | Pvt Dock | Kayaks | Firepit | 1g | W/d - Berkshire County, MA
9.9 282 reviews

Lakefront | Pvt Dock | Kayaks | Firepit | 1g | W/d

apartment, Becket
This charming two-bedroom cottage is located in the Sherwood Forest Community, a peaceful lakeside location just 30 kilometres from the Kripalu Center for Yoga and Health in Stockbridge, MA. The property has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The accommodation features a spacious living room with panoramic lake views, a fully equipped kitchen, and two bedrooms that comfortably sleep up to five guests. Guests can enjoy the private beach and dock, go kayaking or canoeing, relax by the fire pit, or practice yoga on the dock.

Top cities

Best Berkshire County, MA holiday apartments with air conditioning

Penthouse Apartment On Park Street - Berkshire County, MA
9.6 14 reviews

Penthouse Apartment On Park Street

apartment, Adams
This 1-bedroom flat in Adams is situated a 3-minute drive from Mount Greylock State Reservation and a 4-minute drive from George Bowe Park, with Adams Theatre a 2-minute walk away.
This accommodation offers air conditioning, sleeps up to three guests, and is conveniently located for exploring attractions such as Jiminy Peak Mountain Resort and the Berkshire Scenic Railway Museum.

Frequently asked questions about apartment rentals in Berkshire County, MA

  • What is Berkshire County, Massachusetts, famous for?

    Berkshire County is renowned for its stunning natural beauty, encompassing rolling hills, picturesque mountains, and numerous lakes and rivers. It's also a significant cultural hub, boasting world-class performing arts venues like Tanglewood (the summer home of the Boston Symphony Orchestra) and Jacob's Pillow Dance Festival. The area is also known for its charming towns, historic sites, and thriving arts and crafts scene.
  • What are the best apartments in Berkshire County, MA?

  • What are some off-the-beaten-path spots to check out in Berkshire County, Massachusetts?

    For a less crowded experience, consider exploring the Mount Greylock State Reservation, offering breathtaking panoramic views from the highest point in Massachusetts. The Ashuwillticook Rail Trail provides a scenic walk or cycle through tranquil countryside. Also, check out the smaller, less-visited museums like the Norman Rockwell Museum in Stockbridge, which is a great alternative to the busier attractions.
  • What are the best apartments with a pool in Berkshire County, MA?

  • When should one visit Berkshire County, Massachusetts, for the best experience?

    The best time to visit depends on your priorities. Summer (June-August) offers warm weather ideal for hiking and outdoor activities, alongside the peak season for cultural events like Tanglewood and Jacob's Pillow. Autumn (September-October) brings vibrant foliage, making for spectacular scenic drives and hikes. Spring and winter offer quieter experiences, with winter providing opportunities for skiing and snowboarding at various resorts in the area.
  • What are the best apartments with a jacuzzi in Berkshire County, MA?

  • Are there any cultural festivals unique to Berkshire County, Massachusetts?

    Yes, Berkshire County hosts several unique cultural festivals. The Tanglewood Music Festival is a major summer event featuring the Boston Symphony Orchestra. Jacob's Pillow Dance Festival showcases diverse dance styles from around the world. The Great Barrington Fair is an annual agricultural fair with local crafts and entertainment. Many smaller towns also have their own unique festivals throughout the year.
  • What are the best apartments for families and kids in Berkshire County, MA?

  • What sports or recreational activities are a big draw in Berkshire County, Massachusetts?

    Berkshire County offers a wide range of recreational activities. Hiking and mountain biking are popular in the numerous state parks and forests, including Mount Greylock State Reservation. During winter, skiing and snowboarding are popular at Butternut Basin and other resorts. Canoeing, kayaking, and fishing are available on several lakes and rivers. Golfing is also a popular pastime, with several courses in the region.
  • What are the best pet friendly apartments in Berkshire County, MA?

  • How can one best interact with locals to learn about Berkshire County, Massachusetts's traditions?

    The best way to learn about local traditions is to engage with the community. Visit local farmers' markets, where you can chat with vendors about regional produce and practices. Stop by local shops and businesses in smaller towns; engaging with the owners often reveals insights into the area's history and culture. Attending local events and festivals provides opportunities for interaction with residents.
  • What are the best apartments with parking in Berkshire County, MA?

  • What are the best local dishes to try in Berkshire County, Massachusetts?

    Berkshire County offers a variety of culinary experiences. You should try the local maple syrup products, which are renowned for their quality. Many restaurants feature locally sourced ingredients in their dishes, showcasing seasonal produce and regional specialties. Look for restaurants that highlight New England cuisine, often incorporating seafood and hearty, seasonal dishes.
  • What specific items should one pack for a trip to Berkshire County, Massachusetts?

    Pack comfortable walking shoes, as you'll likely be doing a lot of exploring on foot. Layers of clothing are recommended, as the weather can be variable, especially during shoulder seasons. A raincoat is always a good idea, regardless of the time of year. If you plan on hiking, bring appropriate gear, including sturdy boots and insect repellent.
  • What are the top sights to visit in Berkshire County, Massachusetts?

    Among the top sights are Tanglewood, the summer home of the Boston Symphony Orchestra; the Norman Rockwell Museum in Stockbridge; Mount Greylock State Reservation for hiking and scenic views; and the many charming historic towns like Lenox, Stockbridge, and Great Barrington, each with its unique character and attractions.

Nearby regions

Best Berkshire County, MA holiday apartments with parking

Berkshire Retreat|king Bed|wi-fi|2m Ski Resort - Berkshire County, MA
9.8 169 reviews

Berkshire Retreat|king Bed|wi-fi|2m Ski Resort

apartment, Great Barrington
This stylish one-bedroom apartment is located just 1.6 kilometres from the centre of Great Barrington and 2.1 kilometres from the Mahaiwe Performing Arts Centre, offering easy access to restaurants, shops, and cultural attractions. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The apartment is ideal for couples, offering a comfortable king-size bed with high-quality linens. Guests can enjoy amenities such as air conditioning, a garden, a swimming pool, parking, and high-speed internet.
Becket Home W/ 3-season Porch: Walk To Lake Access - Berkshire County, MA
9.6 11 reviews

Becket Home W/ 3-season Porch: Walk To Lake Access

apartment, Becket
This two-bedroom apartment is situated in the Sherwood Forest district of Becket, just 0.6 kilometres from the Sherwood Shoppe and within an 8-kilometre radius of Jacob's Pillow.
The 76 square metre property boasts a private backyard with a fire pit, a screened porch, and access to canoes, paddleboards, and life vests for exploring the lake, accommodating up to 7 guests.
Becket Home W/ 3-season Porch: Walk To Lake Access - Berkshire County, MA
9.6 10 reviews

Becket Home W/ 3-season Porch: Walk To Lake Access

apartment, Becket
This Becket holiday home boasts stunning Lake Robinhood views, is within walking distance of the Sherwood Shoppe, and a short drive from Jacob's Pillow and October Mountain State Forest.
Sleeping up to seven guests, this two-bedroom property offers a fully equipped kitchen, a private backyard with fire pit, in-unit laundry facilities, plus access to four kayaks, a canoe, and a paddleboard for exploring the lake.
Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4 - Berkshire County, MA
9.8 9 reviews

Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4

apartment, Hancock
This Hancock, Massachusetts apartment is located at the base of Jiminy Peak Mountain Resort, offering easy access to Lanesboro, Pittsfield, and North Adams, all within a short driving distance.
This 46 square metre (approximately 495 square feet) self-catering flat features a unique gamer-themed design, sleeps four guests, and includes a fully equipped kitchenette, a PlayStation 4, and access to Jiminy Peak's amenities such as a heated swimming pool and hot tub.

Best Berkshire County, MA apartment rentals with a garden

Gorgeous Mountain View Suite Ski On/off At Jiminy - Fully Redone Decor - Berkshire County, MA
10 3 reviews

Gorgeous Mountain View Suite Ski On/off At Jiminy - Fully Redone Decor

apartment, Hancock
This Hancock apartment building enjoys a slopeside location near Jiminy Peak Mountain Resort (within 3.2km), also within 9.7km of Mount Greylock State Reservation and Taconic Ridge State Forest.
This 46 square metre self-catering apartment sleeps four, boasting two bedrooms, one bathroom, a fully equipped kitchen including a dishwasher, on-site indoor pool and fitness centre, plus ski-in/ski-out access and proximity to the Alpine Super Slide and Mountain Coaster (within 3.2km).
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