Vacation rentals in Berkshire County, MA

2512 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 2512 accommodations in Berkshire County, MA, here are the 4 best family friendly rentals

Cozy Rustic Cabin With Scenic Views - Berkshire County, MA
No reviews

Cozy Rustic Cabin With Scenic Views

farm, Hoosick Falls
This secluded 150-acre eco-retreat cabin in the Grafton Mountains, approximately 0.7 miles from its parking area, offers a genuine outdoor experience near Hoosick Falls, with private access to trails leading to Long Pond, Shaver Pond, and Mill Pond.
This rustic glamping site features an outdoor cooking area, fire pit, solar lighting, an outdoor shower, and a private outhouse, with opportunities for wildlife viewing and shuttle service available for the 0.7-mile access from parking.
Cozy Cottage In The Berkshires On 1.6 Acres - Berkshire County, MA
8.6 8 reviews

Cozy Cottage In The Berkshires On 1.6 Acres

apartment, Hancock
This modern rustic cottage in Williamstown offers a rural setting, located 1 mile from the Williamstown Theatre Festival and 62 Center for Theater and Dance, and 2 miles from Jiminy Peak Mountain Resort and Waubeeka Golf Links.
This 1100 sq ft apartment accommodates up to 5 guests with 2 bedrooms and 1 bathroom, featuring a queen bed and three twin beds, a clawfoot tub, a fully-equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, internet, and parking.
Deluxe Yeti Suite On Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn - Berkshire County, MA
9.8 22 reviews

Deluxe Yeti Suite On Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

apartment, Hancock
This ski-in/ski-out apartment is nestled in the mountains of Hancock, just 0.1 miles from Jiminy Peak Mountain Resort and within 9 miles of Zema's Nursery and Pittsfield State Forest. It has an excellent user rating.
The apartment has 1 bedroom, 1 bathroom, and a floor area of 500 square feet. It can accommodate up to 4 guests. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a fitness center, and parking. Activities and features include ski-in/ski-out access, an indoor pool, a fitness center, a fireplace, a DVD player, a refrigerator, and a dryer.
In The Heart Of Jiminy Peak Mountain Resort Slope Side, Shopping Restaurants - Berkshire County, MA
9.4 18 reviews

In The Heart Of Jiminy Peak Mountain Resort Slope Side, Shopping Restaurants

resort, Hancock
JJ Lodge at the Village Center is located in the heart of the Jiminy Peak Mountain Resort in Hancock, within walking distance of ski lifts, restaurants, shops, and other amenities. This "In The Heart Of Jiminy Peak Mountain Resort Slope Side, Shopping Restaurants" offer has received very good user ratings.
The lodge is a one-bedroom, two-bathroom vacation rental that can accommodate up to two guests. It features a private Jacuzzi tub, a cozy fireplace, a queen-sized bed, smart home features, a heated towel warmer, complimentary Wi-Fi, and private gated parking.

Top cities

Best Berkshire County, MA vacation rentals with a balcony

Views Of Catamount!  Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms! - Berkshire County, MA
10 45 reviews

Views Of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!

apartment, Ghent
This spacious home is located in Hillsdale, a rural area about 10 minutes from the Massachusetts border and 30 minutes from the Vermont border. It has received excellent user ratings and is perfect for large groups. The 4,500 square foot home has 5 bedrooms, 5 bathrooms, and can comfortably accommodate up to 14 guests. Enjoy amenities such as a large deck, a screened-in porch, a swimming pond, a full-size pool table, ping pong, a treadmill, a spinner bicycle, and a piano.
Berkshires Mid-century Retreat! - Berkshire County, MA
No reviews

Berkshires Mid-century Retreat!

apartment, West Stockbridge
This West Stockbridge residence offers a unique mountain setting on 14 acres at the end of a dead-end road, providing immediate access to hiking trails just 2 minutes away and exceptional proximity to Tanglewood and Kripalu, both 5 minutes away. This 5-bedroom, 3-bathroom rental features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, terrace, garden, sauna, and parking, located 15 minutes from wineries, 10 minutes from museums, and 20 minutes from skiing.
Lakefront Retreat On Robinson Pond - Stunning Sunrise - Berkshire County, MA
10 23 reviews

Lakefront Retreat On Robinson Pond - Stunning Sunrise

apartment, Taconic Shores
This waterfront vacation home is located in Copake, less than a mile from Copake Town Hall and Town Park, and within 6 miles of Copake Lake and Taconic State Park, offering easy access to both natural beauty and local amenities. The property consistently receives excellent ratings from guests.
This three-bedroom, two-bathroom house can comfortably accommodate up to six guests in its 2,000 square feet of living space. Enjoy amenities like a fully equipped kitchen, a Jacuzzi, a fireplace, a terrace, a garden, a tennis court, and a barbecue grill, perfect for both relaxation and entertainment.
Vermont Summer Getaway  Fire Pit, Yard Games, Near Lake  Sleeps 11 - Berkshire County, MA
10 15 reviews

Vermont Summer Getaway Fire Pit, Yard Games, Near Lake Sleeps 11

apartment, Whitingham
This Whitingham vacation home, situated within three miles of Jacksonville Pond and Harriman Reservoir and six miles of Green Mountain National Forest and H.O. Cook State Forest, offers easy access to outdoor recreation.
This 2,000-square-foot house features four bedrooms, three bathrooms, and accommodates up to eleven guests, boasting a fitness center, jacuzzi, and a fully equipped kitchen.

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

Most Luxury 7000 Sq Ft Log Estate With Swimming Pool, Hot Tub, Sauna, Game House - Berkshire County, MA
10 1 review

Most Luxury 7000 Sq Ft Log Estate With Swimming Pool, Hot Tub, Sauna, Game House

house, Wilmington
This luxurious Vermont log estate is located near Wilmington, approximately 25 miles from the Bennington Battle Monument, 24 miles from the Bennington Museum, and 28 miles from Stratton Mountain.
This 7,000-square-foot vacation home boasts four bedrooms, seven bathrooms, and accommodates up to 19 guests, featuring a private pool, hot tub, sauna, bar, and ample parking, along with free Wi-Fi and laundry service.
Jiminy Peak Country Inn 1 Bedroom Suite - Berkshire County, MA
9.2 168 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

apartment, Hancock
This one-bedroom Hancock apartment, located at the base of Jiminy Peak Mountain in the Berkshires, offers ski-in/ski-out access (snow permitting) and proximity to seasonal restaurants and resort amenities.
The 1-bedroom condo features an open-plan layout with a queen bed, full bath with dual vanities, kitchenette including a small oven, and accommodates up to four guests, boasting a heated pool, hot tubs, gym, and fireplace lounge.
3 Br+ 4level Winter Ski Rental  Looking 4 Seasonal Renter  1 Mile Off Of Jiminey - Berkshire County, MA
9.6 17 reviews

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

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.
Kid-friendly Luxury Mountain Views, Sauna + Office - Berkshire County, MA
10 3 reviews

Kid-friendly Luxury Mountain Views, Sauna + Office

apartment, New Marlborough
This secluded rental home in New Marlborough, situated on 12 private acres in the Berkshires, offers convenient access to hiking trails and swimming, with dining options nearby, and is approximately 2.5 hours from New York City and Boston.
This 3-bedroom, 3-bathroom apartment accommodates up to 6 guests and features a mid-century modern design, a wood-fired sauna, steam shower, a vegetable and herb garden, and is ideal for families with a swing set, trampoline, and baby amenities.

Neighborhoods and points of interest in Berkshire County, MA

Best Berkshire County, MA vacation rentals with a fireplace

Charming Cottage W/ Pool, Fire Pit & Privacy - Berkshire County, MA
9.7 95 reviews

Charming Cottage W/ Pool, Fire Pit & Privacy

apartment, Chatham
This Chatham apartment is located on a secluded, 9-acre property just 2 miles from the town's shops and restaurants, offering a peaceful retreat with easy access to amenities. Guests consistently rate the apartment excellent for its location, cleanliness, and overall experience.
The 3-bedroom apartment comfortably accommodates up to 8 guests, with a spacious living area featuring a wood-burning fireplace, a fully equipped kitchen, and a separate area with two bedrooms and a bathroom for added privacy. Enjoy amenities like a private pool, gardens, lawns, meadows, and wooded paths, perfect for relaxation and outdoor exploration.
Hillsdale Modern Retreat - Berkshire County, MA
9.9 37 reviews

Hillsdale Modern Retreat

apartment, Copake Lake
This mid-century apartment in Hillsdale is located a short drive from the Berkshires, ski resorts, and state parks, offering proximity to farm markets and cideries.
This family-friendly rental accommodates up to 6 guests with 3 bedrooms and 2 spa-like bathrooms, featuring a gourmet kitchen with premium appliances, an Ooni wood-fired pizza oven, a charcoal grill, a 4K home theater, and a dedicated work-from-home den with ultra-fast Wi-Fi.
Three Minutes To Catamount! - Berkshire County, MA
9.8 40 reviews

Three Minutes To Catamount!

apartment, Copake Lake
This Copake Lake apartment is located on a quiet country road, just 15 minutes from Hudson and Great Barrington, and 2 hours from NYC. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This spacious rental is perfect for families or groups of up to 7 guests, with 4 bedrooms and 2 bathrooms. The apartment features a modern kitchen with a dishwasher, a garden, parking, and air conditioning, as well as a peaceful outdoor patio and yard.
The Docent`s House - Honoring A Legacy - Berkshire County, MA
No reviews

The Docent`s House - Honoring A Legacy

apartment, Great Barrington
This story-rich apartment in a rural area of Great Barrington offers convenient access to Ski Butternut (3 miles), downtown Great Barrington (8 miles), and significant Black History landmarks like the W.E.B. Du Bois Boyhood Homesite (15 miles).
This 1750 square foot residence accommodates up to 8 guests with 4 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, Wi-Fi, a washer/dryer, an indoor gas fireplace, and an outdoor dining area.
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