Best apartment offers in Berkshire County, MA

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Berkshire County, MA apartments
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1359 Holiday apartments Berkshire County, MA

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

Among the 1359 accommodations in Berkshire County, MA, here are the 4 best family friendly holiday apartments

Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4 - Berkshire County, MA
9.8 7 reviews
Berkshire County, MA
03/07 – 06/07
334 €/nighttotal: 1002 € (3 )

Game Night Suite At Jiminy Peak Ski Onoff Sleeps 4

1 2
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.
3 Br+ 4level Winter Ski Rental\n Looking 4 Seasonal Renter\n 1 Mile Off Of Jiminey - Berkshire County, MA
9.5 32 reviews
Berkshire County, MA
03/07 – 06/07
846 €/nighttotal: 2538 € (3 )

3 Br+ 4level Winter Ski Rental\n Looking 4 Seasonal Renter\n 1 Mile Off Of Jiminey

4 2
apartment , Lanesborough
This Lanesborough apartment is situated in a mountain setting, less than 5 kilometres from Jiminy Peak Mountain Resort and Mount Greylock State Reservation.
This 163-square-metre property offers four bedrooms, two bathrooms, sleeps ten guests, and boasts a private jacuzzi, terrace, swimming pool, fitness centre, and tennis court, alongside free Wi-Fi.
Vermont Lake Whitingham Mount Snow Area Apartment - Berkshire County, MA
9.7 4 reviews
Berkshire County, MA
03/07 – 06/07
152 €/nighttotal: 456 € (3 )

Vermont Lake Whitingham Mount Snow Area Apartment

1 2
apartment , Whitingham
This Jacksonville apartment, near Whitingham, Vermont, is conveniently located approximately 45km from Bennington and 12.5km from Molly Stark State Park, offering easy access to Mount Snow and other attractions.
This three-bedroom dwelling, boasting 46 square metres of floor space and sleeping up to four guests, features a fully equipped kitchen, free Wi-Fi, private parking, a peaceful garden with patio and fireplace, and on-site yoga classes.
Walk To Campus; Open Concept Kitchen/living;nature Trail At End Of This Quiet St - Berkshire County, MA
8.4 5 reviews
Berkshire County, MA
03/07 – 06/07
368 €/nighttotal: 1104 € (3 )

Walk To Campus; Open Concept Kitchen/living;nature Trail At End Of This Quiet St

3 2
apartment , Williamstown
This Williamstown holiday home is situated a short 0.8 km walk from Lower Linear Park and Williams College, with North Street Conservation Area and Pine Cobble Preserve within a 2.4 km radius.
The three-bedroom property, sleeping five guests, boasts two bathrooms, a fully equipped kitchen including dishwasher, a jacuzzi, garden, terrace, parking, and free Wi-Fi; enjoy nearby walks and outdoor recreation.

Top cities

Best Berkshire County, MA holiday apartments with air conditioning

Spacious One Bedroom W/private Entrance And W/d - Berkshire County, MA
Berkshire County, MA
03/07 – 06/07
138 €/nighttotal: 414 € (3 )

Spacious One Bedroom W/private Entrance And W/d

1 2
apartment , Hancock
This one-bedroom flat is situated in a rural, wooded area of the Berkshires, 4 kilometres from Jiminy Peak Ski Resort and a 20-minute drive from Williamstown.
The 111-square-metre flat accommodates two guests and features a kitchen with an air fryer, air conditioning, and allows pets, with the surrounding area offering opportunities for skiing and exploring the wider Berkshires region.
Cozy Vermont Mini-house - Berkshire County, MA
10 288 reviews
Berkshire County, MA
03/07 – 06/07
341 €/nighttotal: 1023 € (3 )

Cozy Vermont Mini-house

1 2
apartment , Pownal
This Pownal mini-house, a uniquely sculpted dwelling, is situated a short drive (approximately 16km) from the Clark Art Institute, Mass MoCA, and Bennington.
The recently renovated property offers self-catering accommodation for two guests, boasting a queen-sized bed, fully equipped kitchen, and high-speed Wi-Fi, alongside a tranquil wooded setting.
Frankie’s Place - A Mass Moca Neighborhood 2br Apt - Berkshire County, MA
9.7 146 reviews
Berkshire County, MA
03/07 – 06/07
161 €/nighttotal: 483 € (3 )

Frankie’s Place - A Mass Moca Neighborhood 2br Apt

1 2
apartment , North Adams
This North Adams apartment, situated on the first floor and a short walk (less than 1 km) from Mass MoCA, the farmers' market, and Main Street, offers easy access to North Adams' cultural attractions.
The two-bedroom, one-bathroom flat sleeps five guests comfortably, featuring a fully equipped kitchen, a three-season porch, outdoor grill, and fire pit; nearby activities include exploring the Berkshire Museum and enjoying the scenic views.
Cascades Cottage | Stylish Tudor On Gorgeous St. - Berkshire County, MA
9.9 77 reviews
Berkshire County, MA
03/07 – 06/07
389 €/nighttotal: 1167 € (3 )

Cascades Cottage | Stylish Tudor On Gorgeous St.

1 2
apartment , North Adams
This three-bedroom apartment, ideal for six guests, enjoys a prime West End location in North Adams, Massachusetts, abutting the Cascades trail and within a short driving distance (a few kilometres) of downtown, MASS MoCA, and Mount Greylock.
The property features a fully equipped kitchen, stylish vintage décor, indoor and outdoor living spaces including a fireplace, fire pit, sunroom, library, and writing room, plus a private garden, fast Wi-Fi, and parking; pets are welcome.

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

Chic 2br Suite On Jiminy Mtn Sleeps 8 - Gorgeous - Berkshire County, MA
9.6 34 reviews
Berkshire County, MA
03/07 – 06/07
426 €/nighttotal: 1278 € (3 )

Chic 2br Suite On Jiminy Mtn Sleeps 8 - Gorgeous

2 2
apartment , Hancock
This apartment is located in Hancock, just a short walk from Jiminy Peak Mountain Resort and within easy reach of other attractions such as Zema's Nursery and Pittsfield State Forest. It has consistently received excellent reviews from previous guests.
This two-bedroom, one-bathroom property spans 84 square metres and can comfortably accommodate up to eight guests. It features a fully equipped kitchen, a fireplace, a DVD player, and access to a swimming pool, jacuzzi, and fitness centre.
Quaint & Cozy Loft - Berkshire County, MA
10 2 reviews
Berkshire County, MA
03/07 – 06/07
345 €/nighttotal: 1035 € (3 )

Quaint & Cozy Loft

1 2
apartment , Stockbridge
This Stockbridge loft apartment is centrally located, within walking distance of Norman Rockwell's home and Stockbridge village centre.
The one-bedroom flat offers a galley kitchen with fridge, freezer and microwave, a private bathroom, and accommodates two guests, featuring original fireplace and idyllic views.
Berkshires Retreat | Hiking & Swim | Fenced Yard - Berkshire County, MA
10 43 reviews
Berkshire County, MA
03/07 – 06/07
1316 €/nighttotal: 3948 € (3 )

Berkshires Retreat | Hiking & Swim | Fenced Yard

1 2
apartment , Monterey
This five-bedroom, three-bathroom house in the Berkshire Mountains, near Great Barrington, Massachusetts, is seven minutes from Beartown State Forest/Butternut Ski Area and 26 minutes from Tanglewood.
Sleeping up to ten guests, this spacious property boasts a well-equipped kitchen with a 48-inch gas range and dual ovens, four distinct gathering areas including a screened porch and a private fenced backyard with a fire pit, plus fast 1 Gigabit fibre internet and ample parking.
Renovated Apartment On Main St. - Berkshire County, MA
8.4 5 reviews
Berkshire County, MA
03/07 – 06/07
440 €/nighttotal: 1320 € (3 )

Renovated Apartment On Main St.

2 2
apartment , Salisbury
This newly renovated Salisbury apartment, centrally located near Limerock Park and the Appalachian Trail, offers easy access to Hotchkiss School and other local attractions within a few kilometres.
The two-bedroom, one-bathroom flat sleeps five guests comfortably, boasting a fully equipped kitchen with microwave and dishwasher, a private balcony, high-speed internet, and a Roku TV; nearby activities include birdwatching at Hanging Rock Park and tea tasting at Harney and Sons.

Best Berkshire County, MA apartment rentals with a garden

Home In The Berkshires - Berkshire County, MA
9.6 21 reviews
Berkshire County, MA
03/07 – 06/07
515 €/nighttotal: 1545 € (3 )

Home In The Berkshires

4 2
apartment , Hancock
This spacious four-bedroom holiday home is situated on a secluded 1.2-hectare property in Williamstown, Massachusetts, offering convenient access to Jiminy Peak Mountain Resort (800 metres) and the Ashuwillticook Rail Trail (1.6 kilometres).
This 186-square-metre residence accommodates up to eight guests, featuring two master suites, a kitchen with a fridge and dishwasher, and a terrace or balcony, with the surrounding Berkshires providing ample opportunities for outdoor pursuits such as hiking, fishing, and kayaking.
It's All About The Mountain Views, Modern Farmhouse - Berkshire County, MA
9.6 4 reviews
Berkshire County, MA
03/07 – 06/07
315 €/nighttotal: 945 € (3 )

It's All About The Mountain Views, Modern Farmhouse

1 2
apartment , Ghent
This family-friendly holiday home is situated in the mountains, just 20 kilometres from Catamount Aerial Adventure Park, Catamount Ski Area, and Omi International Arts Center. The property has received excellent user reviews, highlighting its comfortable and relaxing atmosphere.
This one-bedroom house can accommodate up to six guests and features a fully equipped kitchen, a spacious living area, and a private garden. Guests can enjoy the spa, jacuzzi, and outdoor barbecue facilities, as well as free Wi-Fi and air conditioning.
Freemans Grove Benevolent Society  Walk To Moca - Berkshire County, MA
9.9 269 reviews
Berkshire County, MA
03/07 – 06/07
185 €/nighttotal: 555 € (3 )

Freemans Grove Benevolent Society Walk To Moca

1 2
apartment , North Adams
This charming flat is situated in the Freeman's Grove neighbourhood of North Adams, just a short walk from MASS MoCA and a steep block from the town centre. It has consistently received excellent ratings for its cleanliness, location and overall experience.
The apartment is laid out with two bedrooms and one bathroom, comfortably accommodating up to four guests. It features a modern kitchen with a fridge and microwave, air conditioning, a garden, parking and internet access, along with a unique artistic vibe, an open floor plan and a cosy sleeping nook.
Lakefront Bungalow - Berkshire County, MA
9.8 11 reviews
Berkshire County, MA
03/07 – 06/07
794 €/nighttotal: 2382 € (3 )

Lakefront Bungalow

3 2
apartment , Otis
This pet-friendly bungalow is located in Otis, Massachusetts, just 7km from Tolland State Forest and close to Otis Reservoir. It has received excellent user ratings and is a popular choice for travellers visiting the area.
The bungalow has 3 bedrooms and 2 bathrooms, comfortably accommodating up to 7 guests. It is fully equipped with modern amenities, including air conditioning, Wi-Fi, a fully equipped kitchen, a washer and dryer, and a spacious garden with a fire pit.
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