Gorgeous Sheffield Home in Heart of Berkshires

See all properties

Entire home

Overview
Amenities
Policies
Location
Host

Exceptional

5 bedrooms3+ bathroomsSleeps 15380.9 sq m

Popular amenities

Dryer
Washer
Kitchen
Barbecue grill
Parking available
Outdoor space

Explore the area

Sheffield, MA

Magnolia Bluffs Casino
‪4 min walk‬
Lake Buel
‪17 min drive‬
Ski Butternut
‪21 min drive‬
Great Barrington, MA (GBR-Walter J. Koladza)
‪16 min drive‬

Rooms & beds

5 bedrooms (sleeps 15)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

3 Single Beds

Bedroom 4

3 Single Beds

Bedroom 5

1 Queen Bed and 2 Single Bunk Beds

3 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Bathtub or shower · Toilet

Bathroom 4

Toilet

Spaces

Deck or patio

Porch or lanai

Kitchen

Kitchenette

Balcony

Outdoor play area

Garden

Dining area

About this property

Our home is a beautiful mountain-style home (exposed beams, wood floors, all new appliances) on a quiet rural road with commanding views of the Housatonic valley and Mt. Everett. Six miles to Great Barrington in the heart of the Berkshires. The house has five bedrooms, two living rooms, loft area and 3.5 bathrooms. We have a wrap-around deck, screened porch, outdoor fire pit and charcoal grill. The home sits on 5 lush acres up a long private drive. Magical!

Property manager

Steve Bileca

Languages

English, French, German, Italian, Spanish

Add dates for prices

Amenities

Kitchen

Washer

Dryer

Air conditioning

Outdoor space

Mountain view

Have a question?

Beta

Get instant answers with AI powered search of property information and reviews.

Ask a question

Similar properties

Sunrise lights up the front of the house. Moon sets over the mountain.

Hot tub
Kitchen
Washer
Dryer

House Rules

Check in after 2:00 PM

Minimum age to rent: 26

Check out before 12:00 PM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy

Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges

Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed

On-site parties or group events are strictly prohibited

Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip

Host has not indicated whether there is a smoke detector on the property

Property Registration Number C0096052670

We should mention

A car is required for transport to and from this property

About the area

Sheffield

Located in Sheffield, this holiday home is in a rural area and in the mountains. Umpachene Falls Park and Les Trois Emme Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Suter Farm and Three Mile Pond Wildlife Management Area. Travelling with kids? Consider Harney and Sons Tea Tasting Room, or check out an event or a game at Lime Rock Park. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Sheffield, MA

What's nearby

Magnolia Bluffs Casino - 4 min walk - 0.4 km
Mahaiwe Performing Arts Center - 15 min drive - 12.8 km
Housatonic River Walk - 15 min drive - 13.2 km
Lake Buel - 17 min drive - 13.3 km
Ski Butternut - 21 min drive - 17.7 km

Getting around

Pittsfield, MA (PSF-Pittsfield Municipal) - 48 min drive

Restaurants

‪McDonald's - ‬15 min drive
‪Caddie Shack - ‬12 min drive
‪Great Barrington Bagel Company - ‬13 min drive
‪Industry Kitchen - ‬14 min drive
‪Bogies Restaurant & Pub - ‬12 min drive

Frequently asked questions

Is Gorgeous Sheffield Home in Heart of Berkshires pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Gorgeous Sheffield Home in Heart of Berkshires?

Check-in begins at 2:00 PM.

What time is check-out at Gorgeous Sheffield Home in Heart of Berkshires?

Checkout is at 12:00 PM.

Where is Gorgeous Sheffield Home in Heart of Berkshires located?

This family-friendly Sheffield holiday home is located in the mountains, within a 10-minute walk of Magnolia Bluffs Casino and Housatonic River. Suter Farm and Thom Reed UFO Monument Park are also within 3 miles (5 km).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

8/10 Good

Kate S.

23 February 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Berkshire

Property was clean and owner was easily to communicate with and responsive

Stayed 2 nights in Feb 2025

10/10 Excellent

Roger S.

28 November 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Happy Birthday to my Wife, Mum, Nana, Child of God,

All was perfect for 2 days of celebration. * Enough room for 8 adults and 3 children. * Beautiful views of Mounts Washington and Everett at 3 floor levels. * Property owner responded to questions, quickly. * Within 3 miles, the Marketplace Kitchen in Sheffield Village provided a wonderfully prepared Vegan dinner, along with delicious vegan cakes.

Stayed 2 nights in Nov 2024

10/10 Excellent

Jill W.

9 September 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location for a large group

The location is beautiful, private and serene. The kitchen is very well stocked for a large group (everything needed to cook and serve many people). The layout is great to maximize privacy for a work related retreat - more single beds were good for us as well. Clean and comfortable!

Stayed 2 nights in Sep 2024

10/10 Excellent

Cindy S.

28 February 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends Reunion Weekend

The house was absolutely perfect for our weekend of reconnecting with friends. The house was clean, we had plenty of space, and the owners were very responsive to any questions we had. The location was also great - secluded enough for a relaxing getaway, but close enough to stores and Great Barrington! Looking forward to staying here again. Highly recommend!

Stayed 2 nights in Feb 2024

10/10 Excellent

Pat H.

29 December 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect For Family Gathering

Our 2nd time here for a family holiday celebration. Three floors for sleeping and gathering, and a huge table with elbow room for all! Very private setting, but close to shopping, restaurants... even a brewery and a distillery for a "sip trip." Excellent communication with the owner...all texts answered within minutes. Our stays have been in winter, so we haven't been able to enjoy the beautiful deck and porch with gorgeous views... maybe we'll have to schedule a warm weather stay in the future!

Stayed 3 nights in Dec 2023

10/10 Excellent

Karen H.

23 July 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful views

Great house for large group!!

Stayed 3 nights in Jul 2023

10/10 Excellent

Greg M.

24 June 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family get-together

Great property and location, and lots of space and amenities for our group of 10 to use. We especially enjoyed the enormous kitchen and the firepit. Owner was very easy to reach, and check-in was the easiest I've ever had at a VRBO.

Stayed 4 nights in Jun 2023

10/10 Excellent

Stephen K.

8 June 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Comfortable and Quiet, great home

I have nothing but good things to say. The home was exactly as described and we had no issues at any point in the process. Would come back here anytime.

Stayed 3 nights in Jun 2023

10/10 Excellent

Johanna T.

5 June 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing place!

Everyone in our group enjoyed the property and had great things to say about it! Would recommend! :)

Stayed 3 nights in May 2023

10/10 Excellent

Barbara M.

30 April 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ladies retreat weekend

We thoroughly enjoyed our visit to the Berkshire’s and this property! Large, clean, well maintained and well outfitted home for a group of 10 women on a weekend retreat. Even with such a large group we were very comfortable and the kitchen/dining fit us all with a few extra spaces! Ample outdoor areas and screened in porch. Beautiful scenery and privacy, yet a short drive to essentials and a quaint New England town. Owners are responsive and kind. Home is well stocked with linens and essentials. Thank you for allowing us to enjoy your beautiful home!

Stayed 2 nights in Apr 2023

10/10 Excellent

Erin L.

26 March 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Framily Getaway

Such a beautiful and accommodating space! Homeowners were friendly, responsive and extremely helpful! Great weekend getaway.

Stayed 2 nights in Mar 2023

10/10 Excellent

Joelle P.

8 March 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

A dream home

The house is gorgeous and fit 8 people comfortably with room to spare. The house exceeded our expectations with beautiful grounds, views and amenities. The kitchen was well stocked, beds were comfortable and the living room was perfect for a large group. The home was spacious and clean, and it was super easy to check in and out. There was snowfall one evening and the road was plowed before we awoke. We will definitely return!!

Stayed 2 nights in Mar 2023

8/10 Good

Federico C., Cambridge

16 November 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

weekend away

property as described/listed. comfortable for 8 adult guests at a good price. amenities all functional as listed. hassle free arrival and departure, responsive hosts.

Stayed 3 nights in Nov 2022

10/10 Excellent

Danielle J., Boston

7 November 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful, private home in heart of Berkshires

We rented this home to host a reunion of friends with four families. The house is large, clean and beautiful. The beds were comfortable, the kitchen was stocked and the views/location were perfect. The home-owner was easy to communciate with and left clear instructions for checking and in and out. There was plenty of space and we loved the wrap around porch and fire pit. Would definitely recommend!

Stayed 2 nights in Nov 2022

10/10 Excellent

Kathy M., Orinda, CA

14 September 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay!

Steve's house in Sheffield was absolutely perfect, and exceeded our expectations based on the photos in the listing! The grounds are beautiful, the house was spacious and clean, and we had everything we needed. We loved the large common areas, including the downstairs game room. The location was very convenient to Great Barrington and other nearby towns. Highly recommend!

Stayed 2 nights in Sep 2022

10/10 Excellent

Whit B.

31 August 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

What a perfect trip!

Thank you for everything. The owners are super awesome and helpful and my friends and I had everything we could have ever needed in this beautiful home. If you rent this house you shan’t regret it!

Stayed 2 nights in Aug 2022

10/10 Excellent

Greg H.

17 August 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property to enjoy with friends and family.

Owner is wonderful. Lots of activities to do in the area. Would recommend to others.

Stayed 3 nights in Aug 2022

10/10 Excellent

Richard S., South China, Maine

23 October 2020

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxation Hill

We rented the house to attend our sons wedding. The location is perfect, on a nice hill with great views and close enough to shops and restaurants. Not to mention the wildlife viewing bear, bobcats and deer eating breakfast every morning in the front yard. The house itself was extraordinary will all the amenities you would ever need, including a garment steamer which came in very handy. The children enjoyed ping pong and the adults the fire pit. The rooms were large and comfortable and the internet was strong. The sleeping areas were all very comfortable and with 4 bathrooms there was no waiting! Our host Steve checked in on us and made sure we were all set for a very relaxing stay. One of the best properties we have ever rented on VRBO and we would not hesitate to recommend this property to anyone. Five stars all around.

Stayed 5 nights in Oct 2020

10/10 Excellent

Erin M.

29 July 2020

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spectacular house, property, view

My family and I gathered at Steve's place for a family reunion, and we couldn't have asked for a better space for all of us to gather. The view is spectacular. We loved roasting marshmallows around the fire pit at night or chilling outside or on the screened porch. The kitchen is massive and has a nice long table for a big group as well. There are plenty of beds and space for indoor hangs as well. The property is very private, and we enjoyed really feeling like we had gotten away from the city. It's minutes away from great hikes and about 15 min from Great Barrington, which is a fun town to walk around in as well. Highly recommend!

Stayed 5 nights in Jul 2020

10/10 Excellent

Joan H., Philadelphia, PA

10 July 2020

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Perfect Retreat in the Berkshires

This is a lovely, secluded home with a large, well-equipped kitchen, comfortable sleeping areas, and spacious indoor/outdoor areas for all of us to relax and share meals. Steve is a perfect host and provided great suggestions for road biking, swimming and hiking. Six adults and one toddler had the most wonderful family vacation.

Stayed 7 nights in Jul 2020

10/10 Excellent

Sara D.

21 November 2019

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect house for reunion weekend

A group of us girl friends had an amazing weekend away. The house was perfect. Beautiful view. Plenty of bedrooms for everyone, and a huge kitchen with a perfect kitchen table for a big group meal! Thanks!

Stayed 2 nights in Nov 2019

10/10 Excellent

Alexandra B.

30 August 2019

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful, peaceful!

We had a wonderful experience renting this property! It was in close proximity to grocery store, bagel shop, restaurants, hiking, winery, and brewery. But it’s also perfect for just staying in! Huge property (inside and out) - wish we could’ve stayed a week to fully take advantage!

Stayed 2 nights in Jul 2019

10/10 Excellent

Kathleen M.

10 July 2019

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for our Family Reunion!

This house exceeded our expectations as a place to get our far flung family together for a reunion! The layout of the house is perfect for a large gathering! The huge kitchen table and large patio dining table made gathering for meals easy and pleasurable. The basement area, which we used as the kids space, with its ping pong table, bunk rooms, plenty of space for play, and access to the yard was great! It allowed the kids to have loud play space while adults gathered in the living room to visit and enjoy the fantastic view of the Berkshires. Kitchen is well equipped for cooking, beds and bedding were comfortable, baths were clean and spacious. This house is so well set up and just easy and comfortable to be in, it definitely added to the pleasure of our reunion and we felt lucky we picked this spot. We were nervous about picking a house for this special gathering online, there is always the possibility that the house won't live up to its description or photos. We felt this one exceeded both and we thoroughly enjoyed our stay there! By the way, take the owner's direction to not put your trash outside seriously, there are active black bears throughout the area and we got a close view of one that stopped by just as we were leaving the house one morning. Thankfully we didn't have any trash or food outside, but she was definitely checking for it! Overall a fantastic spot, we would rent it again in a heartbeat! Thanks to the owners for offering this space for rent and being available to help us with any questions we had.

Stayed 4 nights in Jul 2019

10/10 Excellent

Mark B., Southbury, Connecticut

2 June 2019

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome place to stay!

This is our third year back at this house and I highly recommend this location. Steve is very easy to work with. He is responsive and always willing to help. The house is clean and roomy and was prefect for our group of 14 for our golf weekend in the Berkshires. Already looking forward to next year.

Stayed 3 nights in May 2019

10/10 Excellent

Travis T.

5 December 2018

Great family stay, owners were excellent and easy to communicate with.

Property was a perfect setup for our big family gathering. Beautiful scenery abounds, and the house is a great setup for a big group. We will be back!

Stayed 2 nights in Nov 2018

About the host

Hosted by Steve Bileca

Steve is the Head of School at an independent school in Vail, Colorado. He grew up on the East Coast but lived abroad, as well as in Chicago, San Francisco and New York before settling in Vail. Angela is a life-long educator as well, and grew up in Sevilla, Spain.

Why they chose this property

We fell in love with the Berkshires for its natural beauty, cultural riches and lifestyle. Sheffield is a wonderful community in the heart of a very special region in the Northeast.

What makes this property unique

The endless views of Mount Everett and the surrounding landscape; the proximity to cultural venues such as Tanglewood; the recreational opportunities at the nearby lakes and parks, the hiking and biking.

Languages:

English, French, German, Italian, Spanish

Tell us how we can improve our siteShare feedback

Gorgeous Sheffield Home in Heart of Berkshires

Photo gallery for Gorgeous Sheffield Home in Heart of Berkshires

Reviews

Popular amenities

Explore the area

Rooms & beds

5 bedrooms (sleeps 15)

Bedroom 1

Bedroom 2

Bedroom 3

Bedroom 4

Bedroom 5

3 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Spaces

About this property