Entire home

Family Friendly in Sheffield, private yet close to everything!

Photo gallery for Family Friendly in Sheffield, private yet close to everything!

Exterior
Living area
Private kitchen
Dining
Living area

Reviews

10 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Deck or patio
  • Toys
  • Barbecue
  • Internet access
  • Pet-friendly
  • Air-conditioning

Explore the area

View map
Sheffield, MA
  • Place, Housatonic River
    ‪11 min drive‬
  • Place, W.E.B. Du Bois Boyhood Homesite
    ‪14 min drive‬
  • Place, Catamount Ski Area
    ‪16 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪47 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Bedroom 3- Full

1 Double Bed

Bedroom 4- Bunk

1 Single Bunk Bed

First Floor Master

1 Queen Bed

Second Floor Master

1 King Bed and 1 Single Bed

3 bathrooms, 1 half bathroom

First floor master

Bathtub or shower · Toilet · Jetted bathtub

Powder Room

Toilet

Second floor master

Toilet · Shower only

Upstairs bath

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Separate dining area
Outdoor play area
Garden
Dining area

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About the area

Sheffield

Located in Sheffield, this holiday home is in a rural area. W.E.B. Du Bois Boyhood Homesite and Ashley House are local landmarks, and some of the area's activities can be experienced at Catamount Ski Area and Catamount Aerial Adventure Park. Travelling with kids? Consider Mahaiwe Performing Arts Center and Harney and Sons Tea Tasting Room. Take in the nearby slopes with cross-country skiing and snowboarding, or try out other outdoor activities such as ice skating and sledging.
View more Holiday homes in SheffieldOpens in a new window
Map
Sheffield, MA

What's nearby

  • Housatonic River - 11 min drive - 5.4 km
  • Thom Reed UFO Monument Park - 12 min drive - 6.1 km
  • W.E.B. Du Bois Boyhood Homesite - 14 min drive - 11.7 km
  • Catamount Ski Area - 16 min drive - 13.9 km
  • Taconic State Park - 18 min drive - 17.0 km

Getting around

  • Hudson, NY (HCC-Columbia County) - 39 min drive

Restaurants

  • ‪Guido’s Kitchen - ‬15 min drive
  • ‪Café Holli - ‬16 min drive
  • ‪Cumberland Farms - ‬16 min drive
  • ‪Dunkin' - ‬15 min drive
  • ‪Mom's Country Cafe - ‬9 min drive

Frequently asked questions

Is Family Friendly in Sheffield, private yet close to everything! pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Family Friendly in Sheffield, private yet close to everything!?

As of 28 Oct 2026, prices found for a 1-night stay for 2 adults at Family Friendly in Sheffield, private yet close to everything! on 25 Apr 2027 start from AU$3,564, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Family Friendly in Sheffield, private yet close to everything!?

On-site parking is available at the property.

What time is check-in at Family Friendly in Sheffield, private yet close to everything!?

Check-in begins at 4:00 PM.

What time is check-out at Family Friendly in Sheffield, private yet close to everything!?

Checkout is at 11:00 AM.

Where is Family Friendly in Sheffield, private yet close to everything! located?

This family-friendly Sheffield holiday home is located in a rural location, within 3 mi (5 km) of Thom Reed UFO Monument Park and Mount Everett State Reservation. Housatonic River and Jug End State Reservation are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 65 out of 66 reviews
Rating 8 - Good. 1 out of 66 reviews
Rating 6 - Okay. 0 out of 66 reviews
Rating 4 - Poor. 0 out of 66 reviews
Rating 2 - Terrible. 0 out of 66 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very family friendly. Beautiful grounds.
Stayed 5 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect country get away for a multi generational family. Close to the arts, recreation, and restaurants but a secluded sanctuary as described by the name Peacefield.
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

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

Great weekend in Berkshires

We love coming here. Great house, garden, location and hosts! Perfect.
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

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

Special memories

I have stayed at this home with family during very special family celebrations. It is a wonderful spot and the owner and family are so warm and welcoming.
Stayed 4 nights in Nov 2024
Verified review

10/10 Excellent

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

Beautiful, well-stocked, with great open spaces!

This is one of the best VRBOs we have ever stayed in. The house is gorgeous, very well maintained, and well-stocked. The landscaping and surrounding area is also beautiful. It is a great location for spending time in Great Barrington.
Stayed 3 nights in Sep 2024
Verified review

10/10 Excellent

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

Great stay

This is an adorable home, and we really enjoyed our stay. There was a glitch early on, though the owner was very responsive and had the issue resolved quickly. Will definitely be looking to see if this home is available for our next visits to the area!
Stayed 2 nights in Jan 2024
Verified review

10/10 Excellent

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

Amazing!

Property was amazing and plenty of space for two families and two dogs!
Stayed 3 nights in Dec 2022
Verified review

10/10 Excellent

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

Great family get away!

This place is perfect for a big or small gathering of loved ones. The house is stocked with everything you will need to cook a nice meal or just hang out. We even lost power one night and the generator didn't skip a beat! Can't go wrong booking this place.
Stayed 2 nights in Nov 2024
Verified review

10/10 Excellent

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

Perfect Week

I celebrated Christmas week with family at the property and we had a wonderful visit. It was so peaceful, relaxing and everyone enjoyed their stay. Close to Great Barrington with lots to do but also feels like you are in the middle of nowhere.
Stayed 7 nights in Dec 2024
Verified review

10/10 Excellent

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

A piece of heaven…

We had a lovely stay in this beautiful home tucked away in the Berkshires. The home was just as described and was a perfect place for our family and friends for the weekend. Great communication with owner, will definitely stay here again if our travels take us to the Berkshires again.
Stayed 2 nights in Aug 2024
Verified review

8/10 Good

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

Ski trip to butternut

Nice property not, not her from town and ski resorts.
Stayed 7 nights in Dec 2024
Verified review

10/10 Excellent

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

Wonderful weekend getaway

We had such a wonderful time staying at this home! It’s in a rural area far from any other homes and is so beautiful and spacious. Very easy to drive to the nearby towns to grab food and tons of great hikes nearby. Communication was excellent. Highly recommend!!!
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

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

Wonderful

Very delightful and comfort home with convenient but quiet location. Enjoyed the amazing birds, the groundhog, deer and turkey. Just the most beautiful setting and lovely place to stay. Hope to be back soon
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

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

Thanksgiving in Sheffield

Thanksgiving weekend with family, and this home is so warm and inviting and comfortable. Everyone loved the house and felt right at home. Beautiful property to walk and as a bonus we had a dusting of snow to add to the holiday vibe!
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

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

Great Rental House

We had a wonderful stay. House and property is very spacious for our family and our granddaughter loved the playroom downstairs. Abby was very responsive to any questions. We hope to return in the future!
Stayed 4 nights in Oct 2024
Verified review

10/10 Excellent

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

Weekend in the Berks

This house and the surrounding property is absolutely beautiful! There is a view of nature from every window, and it’s quiet and still, so relaxing! Yet it’s only a short drive to the main road and lots of wonderful shops and restaurants and sights. I can’t wait for our next visit.
Stayed 2 nights in Oct 2023
Verified review

10/10 Excellent

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

Great Getaway with Kids

The house was perfect for a chill getaway with friends and kids! The basement is stocked with toys and kept our kids very happy. The yard is huge and offered a the children some much needed room to run and play soccer. The house is well equipped and comfortable. Very clean as well! Would stay again!
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

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

Convenient, flexible & spacious

Great house for groups & families! Home base for our yearly girls trip (now with a few kids in tow), open living space was great for dinner and hanging. Enough bedrooms for separate families & singles. Playroom was a huge hit!
Stayed 2 nights in Nov 2024
Verified review

10/10 Excellent

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

Exceeds Expectations

The house and property were beautiful - very well kept, very well furnished and perfect for 4 couples attending a nearby wedding. Outdoor and indoor spaces were generous - so even with 8 adults, there was space to be together and find 'away time'. We've stayed at VRBO properties for a long time - this is one of the best.
Stayed 2 nights in Jun 2024
Verified review

10/10 Excellent

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

Great Mini Vacation

The house was as beautiful as described. It was clean, furnished warmly and full of natural light. Anything you might need was available in the home’s kitchen. The owner Abby was very accommodating and very pleasant and friendly Strongly recommend this property
Stayed 4 nights in Nov 2024
Verified review

10/10 Excellent

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

Beautiful property in a great location

We had a short family vacation over the Thanksgiving holiday with our three adult children. This is a spacious country house set on a large private property, nicely decorated and equipped. We loved the proximity to Great Barrington and to the many hiking options in the nearby mountains. The host was friendly and responsive to all our questions and needs.
Stayed 2 nights in Nov 2023
Verified review

10/10 Excellent

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

Berkshire Beauty

We had the most enjoyable stay and loved everything from the tranquil, setting, spacious accommodations, and thoughtful additions. Abigail was a joy to work with, and just wish we had known about this property earlier! Perfection on every level.
Stayed 3 nights in May 2023
Verified review

10/10 Excellent

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

The perfect Berkshire property

Stayed here for Berkshire School graduation and wish we had found this house sooner. Absolutely beautiful property inside and out. First floor primary, gorgeous sun room, perfect bedrooms upstairs. The owners couldn’t have been nicer to deal with. This is a must!
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

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

Beautiful Serene Home with all the amenities!

We had a wonderful time at this home. There were two families each with two kids under the ages of 8. There were plenty of bedrooms, bathrooms and space for the kids to run around. The property is absolutely gorgeous. Close enough to town and the ski resorts but remote enough to feel like you have escaped to the country. We definitely would stay again!!!!
Stayed 65 nights in Dec 2022
Verified review

10/10 Excellent

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

Loved Everything About Our Stay

This property had absolutely everything we needed and then some! It was clean and very well provisioned. The location was private, but close to town. We didn't have any children with us, but kids would love it. Lots of toys and even an outdoor playset. The owner was very helpful and communicated promptly. Can't ask for more.
Stayed 3 nights in Sep 2024
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