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New and Used 2020 Jeep Grand Cherokee for Sale in Cheshire, MA

PRICE DROP
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New
$42,345 $1,500 price drop! MSRP $48,845

2020 Jeep Grand Cherokee Trailhawk

  • Ext. Color: White
  • Int. Color: Other
  • Transmission: Automatic
  • Drivetrain: 4x4/4-wheel drive
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Stephens CDJR of Bennington
() -
(802) 681-0403
5 (42 reviews)
23 mi. from 01225
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Stephens CDJR of Bennington Review
Admin Assistant
by Maureen from Stamford, VT
November 6, 2018
5 5 5 5 5 5 (42 reviews)
Caccious made buying my 2017 Jeep Renegade an easy process. He was very helpful and made buying a car a pleasant experience. I will tell anyone and everyone to go to Stephens and ask for him!! We had friends tell us they worked with Caccious and to ask for him as well. So glad I did!! So so happy!! Thank you!!
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New
$39,365 MSRP $42,365

2020 Jeep Grand Cherokee Upland

  • Ext. Color: Gray
  • Int. Color: Other
  • Transmission: Automatic
  • Drivetrain: 4x4/4-wheel drive
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Stephens CDJR of Bennington
() -
(802) 681-0403
5 (42 reviews)
23 mi. from 01225
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Stephens CDJR of Bennington Review
Jeep purchase
by Lauren from Bennington, VT
November 6, 2018
5 5 5 5 5 5 (42 reviews)
Pleasant buying experience. Caccious was friendly and knowledgeable. Would recommend him and this dealership to anyone.
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New
$37,285 MSRP $40,285

2020 Jeep Grand Cherokee Laredo

  • Ext. Color: White
  • Int. Color: Other
  • Transmission: Automatic
  • Drivetrain: 4x4/4-wheel drive
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Stephens CDJR of Bennington
() -
(802) 681-0403
5 (42 reviews)
23 mi. from 01225
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Stephens CDJR of Bennington Review
Jeep Lease
by Elisha R from Bennington, VT
December 6, 2018
5 5 5 5 5 5 (42 reviews)
Very helpful sales consultant, Caccious. Went above and beyond to make sure I understood all of my options and made the right decision. Overall great experience.
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New
$41,845 MSRP $44,345

2020 Jeep Grand Cherokee Limited

  • Ext. Color: White
  • Int. Color: Other
  • Transmission: Automatic
  • Drivetrain: 4x4/4-wheel drive
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Stephens CDJR of Bennington
() -
(802) 681-0403
5 (42 reviews)
23 mi. from 01225
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Stephens CDJR of Bennington Review
Great customer service and easy to work with
by JessOB from Pittsfield, MA
December 3, 2018
5 5 5 5 5 5 (42 reviews)
I'm very happy with the quick transaction to get me in my new jeep! Go visit these guys and they will take care of you.
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New
$42,090 MSRP $44,590

2020 Jeep Grand Cherokee Limited

  • Ext. Color: Black
  • Int. Color: Other
  • Transmission: Automatic
  • Drivetrain: 4x4/4-wheel drive
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Stephens CDJR of Bennington
() -
(802) 681-0403
5 (42 reviews)
23 mi. from 01225
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Call
Stephens CDJR of Bennington Review
Best Jeep dealer
by Brian from Farmington, CT
November 5, 2018
5 5 5 5 5 5 (42 reviews)
Worked with Jason via email and drove up from Connecticut on a Saturday to check out a used Wrangler. Jason, Blake, and Wallace were all great to work with - laid back, no pressure, friendly, accommodating. We were out of there in a few hours. It was the easiest car purchase I've made. When it is time, I know we will go back to see they guys again for our next Jeep.
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New
$40,545 MSRP $43,545

2020 Jeep Grand Cherokee Limited

  • Ext. Color: Red
  • Int. Color: Other
  • Transmission: Automatic
  • Drivetrain: 4x4/4-wheel drive
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Stephens CDJR of Bennington
() -
(802) 681-0403
5 (42 reviews)
23 mi. from 01225
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Stephens CDJR of Bennington Review
Excellent customer service and hassle free
by JoshR from Pittsfield
December 3, 2018
5 5 5 5 5 5 (42 reviews)
I purchased a used vehicle from this dealership. The sales personnel were personable, friendly, and helpful. I scheduled a test drive and the car was out and ready when I arrived. They appraised my trade in while I tested the vehicle. They offered a fair trade in and gave me all the time I needed to examine and evaluate the vehicle I was interested in. They made a very fair market offer. Overall it was an excellent experience. I highly recommend this dealership.
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New
$40,545 MSRP $43,545

2020 Jeep Grand Cherokee Limited

  • Ext. Color: Blue
  • Int. Color: Other
  • Transmission: Automatic
  • Drivetrain: 4x4/4-wheel drive
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Stephens CDJR of Bennington
() -
(802) 681-0403
5 (42 reviews)
23 mi. from 01225
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Call
Stephens CDJR of Bennington Review
customer
by Kaci from Readsboro, VT
December 3, 2018
5 5 5 5 5 5 (42 reviews)
Staff was very helpful and thorough with all the vehicle information. Excellent customer service. Didn't take too long to do all the paperwork. I'd recommend this dealership and staff to everyone. Love all the options.
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New
$41,045 MSRP $43,545

2020 Jeep Grand Cherokee Limited

  • Ext. Color: Blue
  • Int. Color: Other
  • Transmission: Automatic
  • Drivetrain: 4x4/4-wheel drive
Save
Stephens CDJR of Bennington
() -
(802) 681-0403
5 (42 reviews)
23 mi. from 01225
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Call
Stephens CDJR of Bennington Review
Jeep buying experience
by Mike jeep fan from Readsboro VT
November 6, 2018
5 5 5 5 5 5 (42 reviews)
Cassius was great. Was very helpful and not pushy. He was great helping me find what I was looking for. I would recommend to others to shop for a new or used vehicle there.
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New
$40,545 MSRP $43,545

2020 Jeep Grand Cherokee Limited

  • Ext. Color: Red
  • Int. Color: Other
  • Transmission: Automatic
  • Drivetrain: 4x4/4-wheel drive
Save
Stephens CDJR of Bennington
() -
(802) 681-0403
5 (42 reviews)
23 mi. from 01225
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Call
Stephens CDJR of Bennington Review
Satisfied customer.
by nadia stewart from BENNINGTON Vt
November 5, 2018
4 4 4 4 4 5 (42 reviews)
Thank you very much . i was very pleased with how helpful the gentlemen were..cant complain very happy customer
New
$41,280 MSRP $41,280

2020 Jeep Grand Cherokee Upland

  • Ext. Color: Black
  • Int. Color: Black
  • Transmission: Automatic
  • Drivetrain: 4x4/4-wheel drive
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Bedard Bros
() -
(413) 776-1174
3.5 (78 reviews)
0 mi. from 01225
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Bedard Bros Review
Awesome Honda Service
by JML from Washington, MA
November 5, 2018
5 5 5 5 5 3.5 (78 reviews)
Brought our 2016 Honda Pilot into the dealership this a.m. for an "Emissions System Problem" - we did not have an appointment, but Scott Miller took our car right in. They were able to reset the error message, they test drove it to be sure it did reset and sent us on our way. Kudos to Scott for the excellent Customer Service, he was very accommodating!
New
$49,140 MSRP $49,140

2020 Jeep Grand Cherokee Trailhawk

  • Ext. Color: Black
  • Int. Color: Red
  • Transmission: Automatic
  • Drivetrain: 4x4/4-wheel drive
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Bedard Bros
() -
(413) 776-1174
3.5 (78 reviews)
0 mi. from 01225
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Bedard Bros Review
Excellent customer service.
by Jennifer G from Dalton Ma
November 5, 2018
5 5 5 5 5 3.5 (78 reviews)
I went there just to look, I certainly did not think I would be getting a car that day! Nate Dudziak, my sales person so helpful and approached everything with a we can make that happen attitude, it was very refreshing and at the end of the day I had a new Volvo. Nate and Steve put together a package that worked for me. The entire experience was top notch.
New
$55,675 MSRP $55,675

2020 Jeep Grand Cherokee High Altitude

  • Ext. Color: Blue
  • Int. Color: Black
  • Transmission: Automatic
  • Drivetrain: 4x4/4-wheel drive
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Bedard Bros
() -
(413) 776-1174
3.5 (78 reviews)
0 mi. from 01225
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Bedard Bros Review
Kathy Burgess and the Bedard Bros. Team
by Julie Pelletier from Pittsfield, MA
November 6, 2018
5 5 5 5 5 3.5 (78 reviews)
I couldn't agree more with your Featured Reviewer. I just bought my first Bedard Honda, a gorgeous, pre-owned CR-V, from Kathy Burgess and the experience was exceptional. I've been taking my previous car, a Honda Civic, to Bedard for the last 5-6 years since my husband and I moved to the Berkshires and have always been very pleased with the on-time and accurate service I've received. So when it came time for a replacement, I began by first looking at the pre-owned cars Bedard had and found one that I test drove and that interested me. But I decided to look further to be sure I wasn't missing something better in our price range. I returned to Bedard to find that the one I liked had been sold but Kathy said that they had just gotten in another that I might like. When she drove it around to the front, I knew it was "the one". She knew exactly what I wanted and, from then on, Kathy took care of every detail and made sure it all came together for me on the day we were to pick it up. She and her Manager, Mike, are an unbeatable team. She now has a special place in my heart too!
New
$43,425 MSRP $43,425

2020 Jeep Grand Cherokee Altitude

  • Ext. Color: Black
  • Int. Color: Black
  • Transmission: Automatic
  • Drivetrain: 4x4/4-wheel drive
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Bedard Bros
() -
(413) 776-1174
3.5 (78 reviews)
0 mi. from 01225
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Bedard Bros Review
Incredible customer service, quick and easy!
by Eric Petersen from Hancock, NY
December 3, 2018
5 5 5 5 5 3.5 (78 reviews)
I called them up days prior to my visit and they walked me through everything and had my paper work and vehicle ready for when I arrived. The vehicle I wanted was in exceptional condition and well priced. My representative’s name was Tanner and he was beyond helpful. He was polite and very informative. They delivered my car at no cost to me. I called him up days after I received my vehicle and Tanner ON HIS DAY OFF, was still able to help me with my questions and concerns. I highly recommend this place and make sure you get Tanner. You can’t go wrong!
* Title, other fees, and incentives are not included in this calculation, which is an estimate only. Monthly payment estimates are for illustrative purposes only and do not represent a financing offer from the seller. Other taxes may apply.
The information on vehicles provided in this service is supplied by the seller or other third parties; Cars.com is not responsible for the accuracy of such information. Cars.com provides this service and materials without representations or warranties of any kind, either expressed or implied. See our terms of service for more details.
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