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Great Barrington Massachusetts Vacation Rentals - Home
1 / 10

Great Barrington Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$375

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$375
Per week:$2,500
Pets allowed:Yes
Internet:No

Peaceful home set on 3- acres with mountain views and a sunny Southern exposure. Kitchen is oversized with an eating area and a breakfast bar. Front porch and patio, master bedroom with ample storage and private bath with soaking tub. Extra rooms for work or play space. Attached ...

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1 / 28

Hancock Guesthouse
Studio / 1 Bathroom / Sleeps 1
Guesthouse / Studio / Sleeps 1

from

$145

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:1
Type:Guesthouse
Per night:$145 - $170
Per week:$1,000
Pets allowed:Yes
Internet:Yes

Free Electric Vehicle Charging Station! (240V 40A no J1772) Other combinations and units may be available. Need an extra bathroom/bedroom - just call. The main house has 5 bedrooms, 6 full baths, panoramic views, and a 1000 sq ft Ballroom on the top floor. It is: 1)Centrally...

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Lenox Massachusetts Vacation Rentals - Condo
1 / 9

Lenox Condo
2 Bedrooms / 1 Bathroom / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4

from

$358

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Condo
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:No

HIGH end, modern 2- bedroom condominium/ apartment located in the heart of Lenox Historical Village. Apartment is on a second story with plenty of off street parking. This Spacious 2 bedroom, 1 bathroom condo has all 8 foot pocket doors, 16 foot high cathedral ceilings, as well...

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1 / 10

Becket Home
6 Bedrooms / 2.5 Bathrooms / Sleeps 11
Home / 6 Bedrooms / Sleeps 11

(5)“ Excellent ”5 Reviews

from

$300

/ night

Email Owner
Bedrooms:6
Bathrooms:2.5
Sleeps:11
Type:Home
Per night:$300 - $325
Per month:$9,000 - $9,750
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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Downstairs Bathroom
1 / 8

Stockbridge Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / 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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1 / 37

Great Barrington Home
5 Bedrooms / 4.5 Bathrooms / Sleeps 12
Home / 5 Bedrooms / 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

Bedroom 14, Bathroom 8. 75, Sleeps 60 Sitting amongst the apple and lilac trees is our beautifully restored 1790's Captain Jacob Lincoln farmhouse. Enjoy morning coffee on the porch, arrange for a lobster bake on the shore, walk the meandering trails that make their way through...

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1 / 42

Charlemont Apartment
Studio / 1 Bathroom / Sleeps 4
Apartment / Studio / Sleeps 4

(2)“ Excellent ”2 Reviews

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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Peaceful

“ Excellent ”
April 17, 2015
Great place to recharge, very pet friendly. Loved the setting and the scones, baked fresh every morning.
Mike Reinhard, Concord, CA

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About Berkshires

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 ...

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