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Book Online or call HomeAway Booking Assistance 888-829-7076
Book Online or call HomeAway Booking Assistance 888-829-7076

Pool in the Summer Ski in Winter!

Bedrooms 3
Half Baths1
Space 2,000 sq ft
Property type house
Minimum Stay 2 nights


About the property

3 Bedroom 1.5 bath with Swimming Pool

Family friendly 3 bedroom house in Sheffield, MA located on a lovely unpaved road with meadow and mountain views. 15 minutes from the stores, restaurants, theaters and farmers' market in Great Barrington, MA and convenient to all attractions in the Berkshires. Excellent biking and walking, x-country skiing ,snowshoeing around the home, with almost no traffic. Much of neighboring land is in conservancy, plenty of wildlife, nearby farms with berry picking, hay rides and roadside vegetables.

10 miles to Catamount Ski Area. 14 miles to Ski Butternut!

House has three bedrooms:


1 room with queen bed

1 room with full sized Pottery Barn loft bed and twin sized convertible flokkati couch bed

Finished basement level:

1 room with queen pull out couch with very comfortable inflatable spring mattress.

Spacious country kitchen well equipped for cooking up all your farmers market finds!

Viking stove

Vitamix blender

Omega juicer


Living room

wood stove

Play room

spacious deck with outdoor sectional sofa and dining table

40x20 in ground swimming pool

Fire pit on hillside

Washer and dryer


Cable TV

More Details

Cynthia LaPier
Member since: 2014
Speaks: english, french, spanish, italian
Response time:
Within a few hours
Response rate:
Calendar last updated:
June 2, 2018

About Cynthia LaPier

We live in the Berkshires full time when we are not traveling or at our other home on Martha's Vineyard. The Berkshires are great! Gorgeous landscapes abound, unlimited opportunities for outdoor activities, with great restaurants, culture and people!

Cynthia LaPier purchased this house in 1997

Why Cynthia LaPier chose Sheffield

When I saw this property almost 20 years ago, my breath was taken away. It's located on a network of protected dirt roads with gorgeous views of the Taconic Range - The Appalachian trail runs right along it. The house is cozy in the winter, cool in the summer, full of sunshine and views. The kitchen is great to cook in. In the summer, the pool is the main attraction - its a beautifully landscaped 20x40 in ground pool accessed from the house by the large deck. In the Fall and Winter the views can't be beat and the walking, hiking, x-country skiing, snowshoeing are right outside the door. At the end of the day relaxing with a fire in the wood stove is just the thing.


Sheffield House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 2000 sq ft
House Rules:
  • Check-in: 12:00 PM
  • /
  • Check-out: 12:00 PM
  • Max. occupancy: 6
  • Min. age of primary renter: 25
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only ...
  • Dining Area
  • seating for 6 people
  • 1 Bathroom
  • 1 Half Bath
  • Bathroom 1 - toilet , tub , shower , Soaking tub, walk in tiled shower,
    Bathroom 2 - toilet
  • 3 Bedrooms, Sleeps 6
  • Bedroom 1 - 1 queen
    Bedroom 3 - 1 sleep sofa /futon , Queen sleep sofa with comfortable inflatable/spring mattress
    Bedroom 2 - double LOFT BED and twin convertible
  • Books
  • DVD Player
  • Games
  • Satellite / Cable
  • Television
  • Toys
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • wheelchair inaccessible
Pool / Spa:
  • Heated Pool
  • Private Pool
The house has great WiFi, but some cell phone service is not very good, including AT&T. Our land line is available to guests.


4/5 -
(4 traveler reviews)

75% Complete
0% Complete
0% Complete
0% Complete
25% Complete
Pool in the Summer Ski in Winter!
average rating of 4.0 based on 4 reviews

Beautiful Country Farmhouse in the Berkshires!

  • 5 of 5

We thoroughly enjoyed our stay at this charming farmhouse in the Berkshires! The owner communicated with me well in advance of our arrival and it made our move into the property very easy and seamless...especially after 2 long days of driving from the Midwest! We felt at home in this cozy home for our entire stay!

Upon our arrival, the house was very neat and clean. It was everything I had expected after working with the property owner to plan our arrival. The room where our boys stayed (ages 7 1/2 & 9 1/2) was just redecorated and had a really neat loft bed and single twin lower bed. Our boys alternated beds every night because they both, of course, wanted to sleep in the "cool" loft bed. My husband and I both agreed the master bed was extremely comfortable and we slept the best we had in weeks! Plus, the air conditioning units made it nice and cool in the bedrooms and rest of the house.

This was our first trip to the Berkshires and the owner even sent me a long list of recommended activities to do with our boys each day. The property was just minutes, literally, from 2 beautiful trailheads and just a short drive to Great Barrington! We visited an outdoor Shakespeare play in Lenox which our kids loved! Additionally, I asked the owner for recommendations of where to grocery shop and she recommended Guidos in Great Barrington. We even ordered fresh MA lobsters there and had a lobster boil one night! It couldn't have been a better trip. The owner was always quick to respond to any questions I had during our stay which was a nice touch!

We knew going into the trip that AT & T cellular service was not the best but there was a landline phone at the property that worked very well. My husband took a video conference call in the office one morning for a few hours and the internet signal was fast and worked perfectly!

Between the pool, trampoline for our boys, goats, fresh herb garden, chickens and beautiful mountain scenery this stay exceeded all of our expectations! Plus, I have to add, this home has an AMAZING cook's kitchen! I'm a professional chef and the kitchen was well equipped for everyone's culinary needs!

Thank you again Cindy! We appreciate your hospitality and we appreciate you opening up your lovely home to us!


  • Submitted: Aug 19, 2017
  • Stayed: August 2017
  • Source: HomeAway
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Gray, ME

Complete misrepresentation of sleeping arrangments & unsafe conditions

  • 1 of 5

We were extremely dissatisfied with this rental. The pictures on VRBO did not match what was in the house. There were photos of beds that did not exist and a loft bed that was in the house that was not described in the listing and no photo showing it. My 7 year old would not slept in the loft bed and the only other bed found was a pull out sofa in the basement 2 floors below, this was not an option for her either. The owner lists the basement as one of the bedrooms, there are no egress windows and can not legally be a bedroom. The description says it sleeps 6 people, this is a stretch! There is a queen bed in the master, a twin loft bed, a double pull out sofa in the basement, & a twin pull out that we didn't know existed until after. That leaves 1 normal bed. Had I known that 2 of the sleeping spots were pull out sofas I would NOT of booked this rental...who is comfortable sleeping on a pull out for a week. This house is not to code for fire detectors. There was only 3 working fire detectors for 3 levels. The fire detectors that was supposed to be in the master was taken down and not replaced. It is the owners responsibility to make sure the rental is safe and it was not. I rented this house to be close to my older daughters while they were at dance camp so I needed to to work during the day and when I got the arrival information it says AT&T does not get good coverage. If I had 1 bar it was a miracle and had I known this before I contracted and paid I would not have rented. They have a landline that I emailed the owner if I could use and it took her to the next day to respond after I have already missed some conference calls. She said at that point to use her cell because they were at the beach and not checking email as much. It would have been nice if she would have checked it on Sunday to see if we had any issues. The house was also very cluttered and not they type of rentals we are used to with VRBO. I have been renting from VRBO for years and have never written a bad review. I did approach the owner and all she did was argue that the house sleeps six and said I should have called her. These were issues that could not be resolved. In regards to the fire detectors her comment was that someone must have taken one down, this is unacceptable that she did not check this before she rented to us. I would highly recommend not renting this house as it is a disappointment and the owner is not honestly describing her rental

  • Submitted: Aug 16, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
Owner's Response: Sadly, this was a red flag situation from the start. Kelly's first contact with us was to try to rent our house for less than the set rate. What followed was a scam to pay what she wished. This was our first exposure to this ploy. Kelly contacted us once by email at the beginning of her stay to ask if she could use our land line and to say how much they liked the house and pool. I told her of course and recommended that she text me with any other questions so I could respond promptly. I didn't hear a word from her by text or email until they had left at the end of their week. Then I received an email expressing complete and total dissatisfaction and threatening a bad review unless we paid her a large portion of the rental amount. I replied that I would have been happy to have our handyman come to fix the smoke detector immediately if she had let me know about it. Our guests know that I am always right there when they text with questions. We actually like people to be happy! Our daughter's room was redecorated in June with a Pottery Barn loft bed and convertible flokati couch with memory foam mattress. Unfortunately, We did not update photos to show the new beds before summer started. Nothing else in the house has changed and it sleeps the same number of people. Kelly gave us a choice of a bad review or paying her a large sum of money. We chose the review. We don't "do" threats. We love being owners and renters with VRBO/HomeAway and know this incident is not the norm. We have had only lovely renters and mutually happy rental experiences here and at our home on Martha's Vineyard and look forward to many many more!
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Cozy winter visit

  • 5 of 5

We had a really nice stay over New Years weekend. The house was comfortable and cozy, with lots of toys and games for our granddaughter--who also loved visiting the goats. We're sorry that it was winter, because the pool and patio area looked great!

  • Submitted: Jan 24, 2017
  • Stayed: December 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you! You were wonderful renters. We'd be happy to have you over the summer, if you are back this way.
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Wonderful home for family

  • 5 of 5

A very family friendly home with goats and ducks to greet you as you arrive. The A/C worked even on 85+ degree days. Host was great at communicating. The pool was a great bonus for the kids. It's really not a bad drive to get anywhere in the Berkshires from here. Comfortable beds (even the pull-out couch in the playroom) and ultimately a great home away from home for a week.

  • Submitted: Jul 26, 2015
  • Stayed: July 2015
  • Source: HomeAway
Owner's Response: We are so glad you enjoyed your stay!! You were wonderful renters - thank you! We hope you will come again next summer, or for a ski week this winter. All best, Cynthia
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Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $500

Owner's Cancellation Policy

  • 50% refund if canceled at least 30 days before arrival date.
  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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