Entire home

Gorgeous Sheffield Home in Heart of Berkshires

Overview
Amenities
Policies
Location
Host

Exceptional

5 bedrooms3+ bathroomsSleeps 154100 sq ft

Popular amenities

Dryer
Washer
Barbecue grill
Kitchen
Parking available
Outdoor space

Explore the area

Sheffield, MA

Magnolia Bluffs Casino
‪5 min walk‬
Lake Buel
‪20 min drive‬
Ski Butternut
‪25 min drive‬
Hudson, NY (HCC-Columbia County)
‪56 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

Gorgeous Sheffield Home in Heart of Berkshires

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

Protect your payment — always book on Vrbo

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Find out more

Add dates for prices

Amenities

Kitchen

Washer

Dryer

Air conditioning

Outdoor space

Mountain view

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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

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.

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 - 5 min walk - 0.5 km
Mahaiwe Performing Arts Center - 17 min drive - 15.1 km
Lake Buel - 20 min drive - 15.9 km
Catamount Ski Area - 21 min drive - 19.5 km
Ski Butternut - 25 min drive - 20.8 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

10/10 Excellent

Lisa L.

20 Jul 2025

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

Wonderful stay in the Berkshires

Perfect location for a relaxing stay in the picturesque Berkshires. Beautiful house, comfortable beds, amazing views.

Stayed 2 nights in Jul 2025

8/10 Good

Kate S.

23 Feb 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

Jill W.

9 Sept 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

Erin L.

26 Mar 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

Greg M.

24 Jun 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

Johanna T.

5 Jun 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

Cindy S.

28 Feb 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

Stephen K.

8 Jun 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

Pat H.

29 Dec 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

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Michelle L., Boston

4 Aug 2016

Perfect for Large Groups

We had a group of ten adults and the home accommodated us perfectly. Well spaced out with plenty of bedrooms and bathrooms. Large kitchen with a great dining table able to seat 12+. Amazing outdoor space with screened-in porch, outdoor table, lawn and fire pit. Gorgeous views and is nestled into a relaxing area of the Berkshires. We enjoyed our stay, fit our needs perfectly, and the owners were extremely helpful and responsive. We will recommend this home to others, and hope to return again ourselves!

10/10 Excellent

Joelle P.

8 Mar 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

10/10 Excellent

Barbara M.

30 Apr 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

Lisa Z.

13 Jul 2018

A Gem

Everything about this house is magic. From the beautifully-furnished interiors to the wraparound deck to the view from the ginormous picture window in the living room. Stayed here with extended family for three days in early July, and it was loved by kids and adults alike. Steve was the perfect host (even by email!) and the house was clean and well-prepped for our arrival. The HVAC system is a little tricky to figure out (esp as there was a 90+ day during our stay) but Steve talked me through it and we wound up being fine. The ping-pong table proved a total WIN for the kids, who could not stop playing and having tournaments downstairs. In fact, the kids (and one brave adult) turned the downstairs bedroom with bunk beds into a "clubhouse" where they would lounge and talk baseball into *too* late into the night. But the real find here is (IMHO) the long farm-style kitchen table, which seated all 12 of us comfortably. It's the kind of touch that makes a house like this ideal find for any large family/group of friends seeking a stay in the Berkshires. Recommended outdoor activity for 8 and up: Catamount Aerial Adventure Park. Recommended restaurant in GB: Prairie Whale. Recommended hike (hopefully NOT after a storm): Bartholomew's Cobble. Thanks again, Steve!

Stayed 3 nights in Jul 2018

10/10 Excellent

Roger S.

28 Nov 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

Karen H.

23 Jul 2023

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

Beautiful views

Great house for large group!!

Stayed 3 nights in Jul 2023

8/10 Good

Federico C., Cambridge

16 Nov 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 Nov 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 Sept 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 Aug 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 Aug 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 Oct 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 Jul 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 Jul 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 Nov 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 Aug 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

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

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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

Gorgeous Sheffield Home in Heart of Berkshires

Property manager

Languages

Protect your payment — always book on Vrbo

Add dates for prices

Amenities

Have a question?

Similar properties

Antique Farmhouse Totally Restored

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House Rules

Children

Events

Pets

Smoking

Important information

You need to know

We should mention

About the area

Sheffield

What's nearby

Getting around

Restaurants

Frequently asked questions

Reviews

Exceptional

9.8/10

10/10

10/10

10/10

10/10

Reviews

10/10 Excellent

Lisa L.

Wonderful stay in the Berkshires

Lisa L.

8/10 Good

Kate S.

Berkshire

Kate S.

10/10 Excellent

Jill W.

Great location for a large group

Jill W.

10/10 Excellent

Erin L.

Framily Getaway

Erin L.

10/10 Excellent

Greg M.

Family get-together

Greg M.

10/10 Excellent

Johanna T.

Amazing place!

Johanna T.

10/10 Excellent

Cindy S.

Friends Reunion Weekend

Cindy S.

10/10 Excellent