Berkshires Vacation Rentals, Homes, & More

1-6 of 6 Berkshires Rentals

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Great Barrington Cottage
4 Bedrooms / 2 Bathrooms / Sleeps 8

from

$267

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Cottage
Per night:$267 - $284
Per week:$1,867 - $1,984
Pets allowed:No
Internet:Yes

Located directly on the shore of Lake Buel in Great Barrington just minutes away from Tanglewood, Jacobs Pillow and many other attractions. Our family home boasts a 40 foot screened in porch for dining and enjoying the beautiful lake. All rooms are on one floor and you can drive...

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Becket Massachusetts Vacation Rentals - Home
1 / 10

Becket Home
6 Bedrooms / 2.5 Bathrooms / Sleeps 11

“ Excellent ”5 Reviews

from

$275

/ night

Email Owner
Bedrooms:6
Bathrooms:2.5
Sleeps:11
Type:Home
Per night:$275
Per month:$8,250
Pets allowed:Yes
Internet:Yes

Enjoy the Fall in our New England farmhouse! Cross country ski at Canterbury Farms, only 5 minutes away! Beautifully restored Colonial historical farmhouse (1790) with almost 2 acres of lawn for playing croquet and hanging out in the sun. There is a small pond (unfenced) for frogs...

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2 families 1 vacation!

“ Excellent ”
July 29, 2014
This home was absolutely beautiful! It's a country home and for sure colonial... which we LOVED. We can't say enough good things about the home. Comfort, space, family time. There was no TV, which made us a little nervous with a 9, 12 and 13 year old but the variety of board games and yard space along with the frog pond kept them happy. Quite secluded and peaceful . We truly enjoyed every moment. We had family/friends over for a BBQ and there was tons of space for everyone. I loved the large kitchen and the extra sink. There is no A.C. but having the windows open really gave a nice breeze. We even had to wear sweatshirts a few nights. Sara was great at responding back in a timely matter, with questions and concerns. This home is for sure a place for those who want to relax and get away. We would for sure rent this home again. Thank you so much Sara for the memories our families will cherish. It was great to see the kids be kids... and us parents be kids a bit too. :)
Lisa Baker, Joliet, IL

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Lee Massachusetts Vacation Rentals - Apartment
1 / 20

Lee Apartment
2 Bedrooms / 1 Bathroom / Sleeps 6

“ Excellent ”3 Reviews

from

$175

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Apartment
Per night:$175
Per week:$850 - $900
Pets allowed:Yes
Internet:Yes

Entirely remodeled 19th Century Apartment at Main Street of the Lee , spacious rooms , modern kitchen with first level living , walking distance for all finest shops, restaurants and facilities . Convenient distance to major attraction and enjoyable activities of Berkshire County....

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Cozy and comfortable

“ Excellent ”
October 24, 2014
Great location allows you to walk to restaurants. The home is also a short drive to anywhere in the Berkshires. The only negative is it does not have the charming, comfortable front porch the adjoining unit has.
Jeff Larosa, Montgomery, NY

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1 / 23

Great Barrington Home
5 Bedrooms / 4.5 Bathrooms / Sleeps 12

from

$358

/ night

Email Owner
Bedrooms:5
Bathrooms:4.5
Sleeps:12
Type:Home
Per night:$358 - $500
Per week:$2,500 - $3,500
Pets allowed:No
Internet:Yes

This Elegant Luxury Estate offers 6000+ SF of Living Space on 13+ park- like, sunny acres located within only minutes from the downtown Great Barrington. This fantastic home offers 5 Bedrooms, 4. 5 bathrooms, sweeping dual staircase ending with the magnificent open gallery, ...

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Downstairs Bathroom
1 / 8

Stockbridge Home
3 Bedrooms / 2 Bathrooms / Sleeps 7

from

$300

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$300
Per week:$1,200
Pets allowed:No
Internet:Yes

Beautifully remodeled quaint 1930s home overlooking 5 riverfront acres, with all modern amenities including two full bathrooms, laundry facility, internet access, patio and screened in porch with a gas grill for your use. The kitchen is remodeled and fully stocked with a blender,...

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Charlemont Massachusetts Vacation Rentals - Apartment
1 / 42

Charlemont Apartment
Studio / 1 Bathroom / Sleeps 4

“ Excellent ”1 Review

from

$115

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$115 - $135
Per week:$835 - $870
Pets allowed:Yes
Internet:Yes

BREAKING NEWS: Cavalier Cottage has received, for the 2nd consecutive year, two distinguished awards as 'Top Vacation Rental' and 'Rated Excellence' by FlipKey, a division of TripAdvisor. In their own words… 'Congratulations! Based on exceptional guest reviews and an impressive...

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Unmatched hospitality

“ Excellent ”
October 20, 2013
I was faced with the situation in which I had to find extended stay accommodations(five-to-six months)for myself and my four dogs while on a temporary employment assignment in southern Vermont. Needless to say, that was a challenge at best. I was referred to the 'Cavalier Cottage', and being an animal lover herself, Ms. Butterfield graciously offered her beautiful property to me and "my family", even going so far as to treat my dogs as her own. I highly recommend the 'Cavalier Cottage' for its' "pet-friendy" accomodations, hospitality, peace-and-quiet and tranquility, for those traveling in the area.
Michael E. McConnell, Troutman, North Carolina (USA)

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Visiting the Berkshire Mountain Region in Massachusetts

Families that love New England weather and the great outdoors will have a wonderful time in the Berkshires! Vacation rentals are the perfect option for those looking for a home away from home while on vacation. By choosing to rent a home made available by owner, you’re guaranteed a beautiful, spacious rental that’s much more comfortable than a hotel room. While staying in a Berkshire vacation rental, visitors will have a blast exploring the area’s fun activities and attractions. These rentals fill up fast, so book your spot online in advance to save on costs.
Families staying in Berkshire rentals should know that the best way to get around the region is by car. Rentals are available from many local companies. Public transportation is also available in the area.
Areas within the Berkshires
Visitors interested in checking out Berkshire vacation rentals should know about these great places to visit:
  • Williamstown, known as “The Village Beautiful,” is a picturesque area surrounded by hiking trails and mountains. It features the Hopkins Memorial Forest and the Taconic Trail State Park.
  • Stockbridge is a perfect example of small-town New England. It was represented on the cover of The New York Post by artist Norman Rockwell and featured in the James Taylor song "Sweet Baby James."
  • Otis is a great place to visit for a taste of the great outdoors. With more than 20 ponds and lakes, this is a great spot for fishing and relaxing.
  • Pittsfield, also known as the “hub” of the Berkshires, has much to offer locals and tourists. Lots of shopping, outdoor activities, and fun events are available.
Sightseeing in the Berkshires and Things to Do
While enjoying their vacation rentals, Berkshires visitors have many options to keep them occupied! From museums to outdoor adventures, this area has something for every member of the family.
  • Magic Wings Butterfly Conservatory & Gardens is fun for the whole family! This 8,000-square-foot conservatory houses more than 4,000 tropical and native butterflies year-round.
  • The Norman Rockwell Museum houses the world’s largest collection of his original art.
  • Uncle Don’s Barnyard at Ioka Valley Farm is a wonderful option for families with kids looking for some New England charm. It includes a playground, sandboxes, a hay tunnel, and tons of friendly animals.
  • Zip-lining and water sports are perfect for active families looking for a little adventure! For families visiting in the winter, skiing and snowboarding are great options.
Regional Foods and Dining in the Berkshires
The Berkshires has become known for its farm-to-table approach to food. The food culture in the Berkshires focuses on using the best local, organic, and seasonal ingredients. The Berkshires are home to many award-winning restaurants as well as a few interesting food trails. Foodies staying in local Berkshire rentals will enjoy the Beer & Cider Trail and the Cheese Trail.
Berkshires Weather and Climate
The climate of the Berkshires is typical New England weather: mild summers and snowy winters. August is the warmest month, with temperatures reaching 74 degrees. In January, the daily average is about 27 degrees. The average snowfall in Berkshire County, MA, is 70 inches per year.
When to Visit the Berkshires
Families hoping to book their Berkshire house rentals early should think about visiting during one of the region’s many local festivals. Here are a couple of the most popular events:
  • The Fall Folliage Festival & Parade (late September through early October) has been going strong for more than 55 years! It features seasonal produce, homemade goods, a 5K race, and a fun parade.
  • The Rock, Rattle, & Drum American Indian Pow Wow (August) is a fun festival with native dancing, music, arts and crafts, and much more.
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