Vacation rentals in Berkshire County, MA

1693 available vacation rental offers

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Berkshire County, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Berkshire County, MA

Best family friendly Berkshire County, MA vacation rentals

Among the 1693 accommodations in Berkshire County, MA, here are the 4 best family friendly rentals

Hillsdale Lakeside - Lake Access, Balcony & Bbq - Berkshire County, MA
Berkshire County, MA
07/03 – 07/06
$1600/nighttotal: $4800 (3 )

Hillsdale Lakeside - Lake Access, Balcony & Bbq

3 2
house , Copake Lake
This house in Hillsdale offers direct access to Copake Lake and is 23 miles from the Norman Rockwell Museum and 28 miles from the Tanglewood Musical Center.
This 3570 square foot residence accommodates up to 11 guests with 3 bedrooms and 4 bathrooms, featuring air conditioning, WiFi, a full kitchen with a dishwasher and microwave, a fireplace, a patio, and a balcony.
Disney Magic Suite At Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat - Berkshire County, MA
9.8 21 reviews
Berkshire County, MA
07/03 – 07/06
$386/nighttotal: $1158 (3 )

Disney Magic Suite At Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

1 2
apartment , Hancock
This apartment is located just a short distance from Jiminy Peak Mountain Resort and within easy reach of other attractions like Zema's Nursery and Pittsfield State Forest. It has received excellent user ratings, making it a popular choice for travelers.
The one-bedroom apartment spans 500 square feet and comfortably accommodates up to 4 guests. It offers a range of amenities, including a fully equipped kitchen, a fireplace, a swimming pool, a jacuzzi, and convenient parking.
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
07/03 – 07/06
$978/nighttotal: $2934 (3 )

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

4 2
apartment , Lanesborough
This Lanesborough condo is located less than 3 miles from Jiminy Peak Mountain Resort and Mount Greylock State Reservation, offering easy access to skiing, hiking, and scenic mountain views.
This 1750-square-foot vacation rental boasts four bedrooms, two bathrooms, sleeps ten guests, and includes a fully equipped kitchen, in-unit jacuzzi, and access to a shared pool, fitness center, and tennis court.
5br Berkshire Home Mins To The Mountain - Berkshire County, MA
10 4 reviews
Berkshire County, MA
07/03 – 07/06
$748/nighttotal: $2244 (3 )

5br Berkshire Home Mins To The Mountain

5 2
apartment , Charlemont
This 5-bedroom, 3-bathroom rental home in Charlemont is located a short walk from the Deerfield River and the Charlemont Historical Society and Museum.
This spacious accommodation offers a private garden, terrace, barbecue, and fireplace, with capacity for 12 guests and amenities including Wi-Fi, a full kitchen, and on-site parking.

Top cities

Best Berkshire County, MA vacation rentals with a balcony

Woodland Dream House On Private Pond With Forest And Fields- Warm And Cozy - Berkshire County, MA
Berkshire County, MA
07/03 – 07/06
$1246/nighttotal: $3738 (3 )

Woodland Dream House On Private Pond With Forest And Fields- Warm And Cozy

4 2
farm , Hartland
This Hartland farm stay, 1.4 miles from Tunxis State Forest and within 6 miles of several nature preserves and Lost Acres Vineyard, offers a peaceful countryside escape.
This four-bedroom, two-bathroom rental sleeps six and boasts amenities including air conditioning, internet access, and a jacuzzi; enjoy hiking, wine tasting, and birdwatching nearby.
Vacation Village In The Berkshires - Berkshire County, MA
8.7 5436 reviews
Berkshire County, MA
07/03 – 07/06
$214/nighttotal: $642 (3 )

Vacation Village In The Berkshires

1 2
resort , Hancock
Vacation Village in the Berkshires is located in Hancock, Massachusetts, just 1.6 miles from Jiminy Peak Mountain Ski Resort, offering easy access to both the natural beauty of the Berkshires and nearby attractions. The resort has received very good ratings for location, cleanliness, and overall experience.
Vacation Village in the Berkshires offers a range of rooms and suites with modern amenities and comfortable living spaces. The resort features a fitness center, swimming pool, jacuzzi, tennis court, and more, making it an ideal destination for families and couples looking for a relaxing and active getaway.
Lakeside Berkshires Cabin W/ Private Dock & Views - Berkshire County, MA
Berkshire County, MA
07/03 – 07/06
$458/nighttotal: $1374 (3 )

Lakeside Berkshires Cabin W/ Private Dock & Views

2 2
cabin , Lee
This lakeside cabin in Lee offers a private dock and lake views, located 6.9 miles from Cranwell Spa & Golf Club and 9.5 miles from the Tanglewood Musical Center.
This 1500 square foot vacation home accommodates up to 7 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, internet, a full kitchen, and a terrace.
Cozy Cabin In The Berkshire Resort - Berkshire County, MA
8.2 6 reviews
Berkshire County, MA
07/03 – 07/06
$452/nighttotal: $1356 (3 )

Cozy Cabin In The Berkshire Resort

2 2
cabin , Hancock
This Hancock, Massachusetts mountain home is part of a resort, conveniently located approximately 20 miles from both Tanglewood and the Cranwell Spa & Golf Club.
This 9150-square-foot vacation rental boasts two bedrooms, two bathrooms, and sleeps eight, featuring a fully equipped kitchen, hot tub, private patio, fitness center access, a pool, and a jacuzzi, plus free Wi-Fi and parking.

Frequently Asked Questions about vacation rentals in Berkshire County, MA

  • What are the must-see sights in Berkshire County, Massachusetts?

    Berkshire County boasts many attractions! For art lovers, the MASS MoCA in North Adams is a must, showcasing contemporary art in a massive former factory complex. History buffs should visit the Norman Rockwell Museum in Stockbridge, celebrating the iconic American illustrator's life and work. The Berkshire Museum in Pittsfield offers a diverse collection spanning art, science, and history. And don't forget the stunning scenery at Mount Greylock State Reservation, the highest point in Massachusetts.
  • What are the best Airbnb and vacation rentals in Berkshire County, MA?

    Berkshire Mountain Lodge, Berkshire Village Carriage House - Super Private and A Cozy Retreat In Nature - An Art Lover’s Dream are the most popular Airbnb and vacation rentals in Berkshire County, MA among travelers.

  • Are there unique natural phenomena in Berkshire County, Massachusetts?

    Absolutely! The county's varied landscape offers plenty of natural wonders. Mount Greylock, as mentioned, provides breathtaking panoramic views. The Appalachian Trail traverses Berkshire County, offering stunning hiking opportunities. You'll also find numerous charming waterfalls and cascading streams throughout the region, perfect for a refreshing escape. The diverse flora and fauna are also a highlight.
  • What are the most popular Airbnbs in Berkshire County, MA?

    Among the Airbnbs in Berkshire County, MA, A Cozy Retreat In Nature - An Art Lover’s Dream, Peace And Quiet On The Lake and Honeysuckle Rose Cottage are the most popular ones.

  • What essentials should you bring along for a trip to Berkshire County, Massachusetts?

    Pack for all types of weather, as Berkshire County experiences varied conditions. Comfortable walking shoes are a must, especially if you plan on hiking. Layers of clothing are recommended, as temperatures can fluctuate. Don't forget sunscreen, insect repellent, and a hat, especially during the warmer months. A camera is essential to capture the stunning scenery.
  • What are the best vacation rentals with a pool in Berkshire County, MA?

    Berkshire Mountain Lodge, The Granary At House On Golden Hill and Modern Barn With Loft At House On Golden Hill are the best vacation rentals with a pool in Berkshire County, MA.

  • What famous events or festivals are happening in Berkshire County, Massachusetts?

    The Tanglewood Music Center summer concert series is world-renowned, featuring the Boston Symphony Orchestra. The Berkshire International Film Festival showcases independent films. Numerous smaller town festivals happen throughout the year, celebrating local arts and crafts. Specific dates vary, so checking local event listings before your trip is recommended.
  • What are the best rentals for families and kids in Berkshire County, MA?

    The best rentals for families and kids in Berkshire County, MA are Berkshire Mountain Lodge, Berkshire Village Carriage House - Super Private and Peace And Quiet On The Lake.

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Berkshire County, Massachusetts?

    A daily budget will vary widely depending on your travel style. Budget-conscious travelers might spend around $100-$150 per day, while those seeking more luxurious accommodations and experiences could easily spend $300 or more. This includes lodging, meals, activities, and transportation. Gas prices and accommodation costs should be considered.
  • What are the best rentals or Airbnbs with a jacuzzi in Berkshire County, MA?

  • Where can you find the best restaurants serving local dishes in Berkshire County, Massachusetts, and what are the must-try specialties?

    Berkshire County has a thriving culinary scene. The Red Lion Inn in Stockbridge is a historic landmark with delicious New England fare. In Great Barrington, you'll find many farm-to-table restaurants showcasing local produce. Try the area's maple syrup products, local cheeses, and fresh produce. Many restaurants feature seasonal menus highlighting local ingredients.
  • What are some less-famous attractions in Berkshire County, Massachusetts that are worth the visit?

    Consider exploring the Chesterwood estate, the summer home of sculptor Daniel Chester French, creator of the Abraham Lincoln statue at the Lincoln Memorial. The Pleasant Valley Sanctuary offers beautiful hiking trails and stunning views. The Clark Art Institute in Williamstown, while well-known in art circles, might be less familiar to the general public and houses an impressive collection of European and American paintings and sculptures.
  • What are the best activities for engaging with locals and understanding their culture in Berkshire County, Massachusetts?

    Attend a local farmers market to interact with vendors and sample regional products. Visit smaller towns and explore local shops and galleries. Check out community events and festivals, offering opportunities to meet residents and experience local traditions. Consider staying in a bed and breakfast for a more personalized experience.
  • What unique natural landscapes and terrain features can travelers explore in Berkshire County, Massachusetts?

    Berkshire County offers diverse landscapes. The rolling hills of the Berkshires are iconic. The Housatonic River Valley provides picturesque scenery. The Taconic Mountains offer challenging hikes with stunning views. Numerous lakes and ponds offer opportunities for swimming, boating, and fishing.
  • How many days are ideal for visiting Berkshire County, Massachusetts, and what are some itinerary suggestions?

    Three to five days allows for a good exploration of the area. A possible itinerary could include: Day 1: Explore Pittsfield and the Berkshire Museum. Day 2: Visit the Norman Rockwell Museum and Stockbridge. Day 3: Hike Mount Greylock and enjoy the views. Day 4: Explore the art scene in North Adams at MASS MoCA. Day 5: Relax and enjoy the local culinary scene.

Nearby regions

Best Berkshire County, MA vacation rentals with a sauna

Mt Williams Retreat - Berkshire County, MA
Berkshire County, MA
07/03 – 07/06
$736/nighttotal: $2208 (3 )

Mt Williams Retreat

1 2
apartment , Williamstown
Mt Williams Retreat is a 1-bedroom apartment in Williamstown, 15 miles from the Bennington Battle Monument and 29 miles from Cranwell Spa & Golf Club.
This 500 square foot apartment offers a sauna, spa, concierge, private parking, and free WiFi, with proximity to cycling and hiking trails.
Walk To Williams * Steam Sauna * Ritz-carlton Bed - Berkshire County, MA
10 2 reviews
Berkshire County, MA
07/03 – 07/06
$584/nighttotal: $1752 (3 )

Walk To Williams * Steam Sauna * Ritz-carlton Bed

1 2
apartment , Williamstown
This 360 sq ft guesthouse is located two blocks from Williams College and Spring Street's shops and restaurants, under two miles from the Clark Art Institute, and offers soundproofed construction.
The guesthouse features one bedroom and one bathroom, accommodates up to three guests, and includes a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, garden, sauna, parking, radiant floor heating, a private patio with a fire pit, and a Ritz-Carlton mattress.
Comfortable Berkshires Retreat On Mtn Resort, Siso - Berkshire County, MA
8.4 10 reviews
Berkshire County, MA
07/03 – 07/06
$847/nighttotal: $2541 (3 )

Comfortable Berkshires Retreat On Mtn Resort, Siso

4 2
resort , Hancock
The Comfortable Berkshires Retreat On Mtn Resort, Siso in Hancock, Massachusetts is located 0.6 miles from Jiminy Peak Mountain Resort and within 3 miles of the Alpine Super Slide and Mountain Coaster.
This 12-bedroom, 3-bathroom vacation home offers guests a fitness center, sauna, hot tub, and a fully equipped kitchen, accommodating up to 12 people and featuring family-friendly amenities like an arcade/game room and a garden.

Neighborhoods and points of interest in Berkshire County, MA

Best Berkshire County, MA vacation rentals with a fireplace

Cozy Berkshire Cottage
House-private Fenced Yard - Berkshire County, MA
9.7 21 reviews
Berkshire County, MA
07/03 – 07/06
$214/nighttotal: $642 (3 )

Cozy Berkshire Cottage House-private Fenced Yard

1 2
apartment , North Adams
This North Adams vacation rental is conveniently located near Massachusetts College of Liberal Arts (MCLA), Mass MoCA, and Williams College, offering easy access to area lakes, hiking trails, and skiing.
Sleeping up to six guests in two bedrooms (plus a queen air mattress) and featuring a fully equipped kitchen with fridge, freezer, and microwave, a spacious living room, TVs in each bedroom and the living room, a fenced backyard, deck with grill, and on-site parking, this pet-friendly cottage also includes a bar.
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4 - Berkshire County, MA
10 3 reviews
Berkshire County, MA
07/03 – 07/06
$489/nighttotal: $1467 (3 )

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

1 2
apartment , Hancock
This Hancock condo is located in the Village Center of Jiminy Peak Mountain Resort, directly across from the main ski lift, providing ski-in/ski-out access.
The 650-square-foot unit sleeps four, features a fully equipped kitchen with a Keurig and air fryer, and offers access to a year-round heated pool, hot tubs, and a fitness center.
Whistling Peak - Berkshire County, MA
8.5 2 reviews
Berkshire County, MA
07/03 – 07/06
$487/nighttotal: $1461 (3 )

Whistling Peak

4 2
house , Wilmington
Whistling Peak, a Wilmington vacation home, is located 4.9 miles from Molly Stark State Park and within 25-29 miles of Stratton Mountain and Bennington's attractions.
This 2140-square-foot house features four bedrooms, three bathrooms, and accommodates up to 15 guests, offering amenities such as free Wi-Fi, a fireplace, and a private garden with mountain views.
Cascades Cottage | Stylish Tudor On Gorgeous St. - Berkshire County, MA
9.9 79 reviews
Berkshire County, MA
07/03 – 07/06
$449/nighttotal: $1347 (3 )

Cascades Cottage | Stylish Tudor On Gorgeous St.

1 2
apartment , North Adams
This three-bedroom apartment is located in the West End of North Adams, Massachusetts, just a short walk from downtown, MASS MoCA, and the Cascades Trail. The apartment features a fully equipped kitchen, a private backyard garden, and a cozy fireplace, perfect for relaxing after a day of exploring the area.
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