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Little House in the Woods by Evergreen Home

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Welcome to the Little House!
Exterior detail
Dining for 6
Primary with queen bed and workspace
Cottage kitchen

Reviews

10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 6984 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Sheffield, MA
  • Place, Housatonic River
    ‪2 min drive‬
  • Place, Bartholomew's Cobble
    ‪5 min drive‬
  • Place, Tanglewood Music Center
    ‪40 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪45 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Living room 1

1 Double Sofa Bed

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Deck or patio
Kitchen
Office
Garden
Dining area

About this property

Little House in the Woods by Evergreen Home

Evergreen Home Vacation Rentals invites you to "The Little House," a fresh and serene escape in historic Sheffield. Set back on several acres of private woods and facing a wildlife preserve, this cozy retreat is perfect for hiking, biking, and antiquing.

Enjoy the charm of the Berkshires' oldest town, just 20 minutes from both Butternut and Catamount. Whether you are looking for a weekend of relaxation or a long-term seasonal stay, this home is a quiet sanctuary. Inquire about long-term rates



If you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.

The neighborhood is quiet, five minutes from Sheffield's town center, and ten minutes from Great Barrington's great shops and restaurants.

Guests will have private access to the entire home, and property.

This charming, one level home has everything needed for a quiet Berkshires get away.

The kitchen is fully equipped with appliances making cooking at home simple and boasts an additional prep space that can also be used for extra seating. The kitchen opens up to the living and dining area with a dining table that seats 6. The cozy living room features comfortable seating, a TV, and an extensive book collection to explore. The couch pulls out to accommodate other guests.

The primary bedroom features a queen sized bed and an ensuite bathroom with a tub/shower combo and laundry closet. There is also a desk creating the perfect work from home space. The second bedroom contains a queen sized bed and the full guest bath down the hall has a shower stall.

An enclosed sun porch ensures that you can enjoy the country air without the country bugs! There is a gas grill for guest use as well as a fire pit with Adirondack chairs for relaxing by the fire.

Venture out to ski during the winter months! This home is located 20 min from both Butternut and Catamount.

Having a car will greatly enhance your ability to explore the Berkshires effectively.

⭐️ LOCATION: Set back from the road with several acres of woods behind and a wildlife preserve just across the street. The neighborhood is quiet, 5 minutes from Sheffield’s town center, and 10 minutes from Great Barrington’s shops and restaurants.

⭐️ PETS: A small dog may be allowed on a case-by-case basis. Please reach out before booking. No multiples. A $100 fee applies upon approval.

⭐️ PARKING: Free parking on premises.

⭐️ LONG-TERM / SEASONAL: Weekly and monthly discounted rates available. Can accommodate long-term or seasonal rentals.

⭐️ DAMAGE PROTECTION: Your reservation includes a $20 accidental damage insurance fee, so you can relax and enjoy your stay. If any damage occurs, please notify us so we can arrange timely replacements for the next guest.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 23
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 20 lbs per pet (limit one pet total)
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Smoking

Smoking is not permitted
-No Smoking or vaping -No parties or events on the property -No commercial photography or filming allowed without prior authorization

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
Property Registration Number C0127342670

About the neighborhood

Sheffield

Located in Sheffield, this vacation home is in a rural area. Ashley House and Great Barrington Historical Society & Museum are cultural highlights, and some of the area's attractions include Mahaiwe Performing Arts Center and Harney and Sons Tea Tasting Room.
View more Vacation Homes in SheffieldOpens in a new window
Map
Sheffield, MA

What's nearby

  • Housatonic River - 2 min drive - 1.1 km
  • Bartholomew's Cobble - 5 min drive - 5.0 km
  • Lime Rock Park - 22 min drive - 25.0 km
  • National Shrine of the Divine Mercy - 31 min drive - 33.1 km
  • Tanglewood Music Center - 40 min drive - 44.8 km

Getting around

  • Hudson, NY (HCC-Columbia County) - 46 min drive

Restaurants

  • ‪Dunkin' - ‬9 min drive
  • ‪McDonald's - ‬9 min drive
  • ‪Roma Pizzeria - ‬8 min drive
  • ‪The Southfield Store - ‬20 min drive
  • ‪Industry Kitchen & Bar - ‬8 min drive

Frequently asked questions

Is Little House in the Woods by Evergreen Home pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 20 lbs per pet.

How much does it cost to stay at Little House in the Woods by Evergreen Home?

As of Apr 17, 2026, prices found for a 1-night stay for 2 adults at Little House in the Woods by Evergreen Home on Sep 3, 2026 start from $396, 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?

Onsite parking is available at the property.

What time is check-in at Little House in the Woods by Evergreen Home?

Check-in begins at 4:00 PM.

What time is check-out at Little House in the Woods by Evergreen Home?

Check-out is at 11:00 AM.

Where is Little House in the Woods by Evergreen Home located?

Situated in a rural location, this vacation home is within 1 mi (2 km) of Housatonic River and Bartholomew's Cobble. Ashley House and Lime Kiln Farm Wildlife Sanctuary are also within 2 mi (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 32 out of 34 reviews
Rating 8 - Good. 1 out of 34 reviews
Rating 6 - Okay. 1 out of 34 reviews
Rating 4 - Poor. 0 out of 34 reviews
Rating 2 - Terrible. 0 out of 34 reviews

9.6/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Alison 7.

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

What a great little spot

This was a perfect quiet serene location on a beautiful property. Would love to visit again
Stayed 2 nights in Jul 2022
Verified

10/10 Excellent

J G.

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

Relaxing fall getaway

We had a wonderful stay and look forward to staying again sometime. Quiet, relaxing area.
Stayed 4 nights in Oct 2022
Verified

10/10 Excellent

PATRICIA W.

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

Beautiful Little House in the Berkshires

Well- appointed comfortable cottage in a great location. Lovely weekend!
Stayed 3 nights in Oct 2019
Verified

10/10 Excellent

Corey P.

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

Wonderful!

Lovely property for our month long vacation. Wish we could have stayed longer and hope to come back and stay here every summer!!!!
Stayed 30 nights in Jul 2021
Verified

10/10 Excellent

Victoria G.

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

Sweet Stay in Sheffield!

Property was just adorable! Comfortable and charming.
Stayed 2 nights in Oct 2020
Verified

10/10 Excellent

Jason H.

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

Nice

Nice quaint and quiet place
Stayed 4 nights in Nov 2019
Verified

10/10 Excellent

Neil M.

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

Wedding weekend

House was perfect. Spotless and comfortable! Fantastic location.
Stayed 2 nights in Jun 2023
Verified

10/10 Excellent

Kim C.

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

Quick stay in the Berkshires

Super cute house, great owner that was very reachable and responsive. Looks even better in person. Awesome bath towels!
Stayed 2 nights in Feb 2020
Verified

10/10 Excellent

John N.

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

Little House

A true gem in the middle of a the Berkshires. Absolutely loved our stay. The property was extremely clean, cozy and warming. We’ll definitely be back!! Thank you!!
Stayed 4 nights in Sep 2022
Verified

10/10 Excellent

Stella K.

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

Perfect wedding weekend stay

My husband and my two grown children were attending a wedding in Sheffield and I booked this cottage because of its proximity to the venue. It was charming, clean, and very well-equipped. I would love to return for a longer stay!
Stayed 2 nights in Oct 2022
Verified

10/10 Excellent

Alan M.

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

Peace and quiet

Very relaxing. Just what we needed Near to GB
Stayed 14 nights in Aug 2022
Verified

10/10 Excellent

Meghann F.

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

Lovely Retreat

Property was clean and well appointed. Water has sulfur in it; house is impeccably clean. Great location for local sights and nearby towns. Shana was very responsive and a thoughtful host. Hope to come back some time!
Stayed 4 nights in Oct 2020
Verified

10/10 Excellent

Laurie D.

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

Girls Weekend

Thank you Shana for sharing your lovely home! The property is great and even better than the online photos. The Little House is truly a warm and cozy spot. Look forward to renting again!
Stayed 2 nights in Nov 2019
Verified

10/10 Excellent

Alysa G.

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

Comfy and clean!

We stayed at this property for almost a week and found it to be clean, quiet and very close to my stepdaughter's home in Ashley Falls. Easy drives to all the necessities, good pizza and gas stations. I enjoyed sitting on the screened in porch for breakfast and a late night beverage--we even saw a deer!
Stayed 6 nights in Jun 2024
Verified

8/10 Good

Allan C.

Liked: Check-in, communication, location, listing accuracy

Very nice 2 bedroom room

A very nice two-bedroom, two-bathroom house in a quiet corner of the Berkshires. Recommended.
Stayed 3 nights in Jul 2022
Verified

10/10 Excellent

Patricia

Liked: Cleanliness, amenities, property conditions & facilities, communication
My husband and I (and our pups) wanted to get away for a week and enjoy nature and we found this little place. It was perfect - close to so many hiking trails which kept us active all day. The house is in a nice quiet neighborhood and we appreciate all of the amenities like towels, tissues, paper towels, toiletries, kitchenware, etc. We brought our own stuff not knowing how much the house would have and we didn’t need to use any of our stuff :). The house allowed dogs which is hard to find and it was perfect. The house did not smell like dogs so that was great. Anyway, highly recommend!
Stayed 7 nights in Sep 2025
Verified

10/10 Excellent

Stacey A.

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

A Little Gem!

We had a wonderful stay in Shana's vacation home. The location is in a quiet area on a lovely property a short distance from Great Barrington. Shana has excellent taste in furnishings and we couldn't have been more comfortable. From the Beautyrest mattress to the luxurious towels and sheets, it was a first-class experience for a reasonable price. We wouldn't hesitate to stay here again.
Stayed 3 nights in Oct 2019
Verified

10/10 Excellent

Martha R.

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

Wonderful

We spent a week in this wonderful house. It is spotless -- from floor to ceiling. So comfortable from porch furniture to livingroom, diningroom and beds. Excellent kitchen (really well stocked) for cooking. Great linens and towels. Great a/c. Beautiful lawn -- we were really happy. The host was very attentive. Great linens. Great layout for 2 friends or 2 couples. Or couple and a friend.
Stayed 6 nights in Jul 2022
Verified

10/10 Excellent

Kathy V.

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

Wonderful Month at the Little House in the Woods

My Husband and I had a wonderful month at the House in the Woods. This is a lovely home in a truly wonderful area. The house is down the road from great hiking and surrounded by hillsides with glorious views for biking. There are so many sweet and special spots to explore nearby it would take paragraphs to list them. It is perfectly situated for exploring everything the area has to offer. Shana is an excellent Host and we were so happy to be back at the house for a second visit. Thank you Shana. Our Best, Kathy and Alex
Stayed 46 nights in Mar 2021
Verified

10/10 Excellent

Judiann D.

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

Relaxing Reunion

My family greatly enjoyed staying at the house for a long weekend. My family and I had not seen each other for 1.5 years due to COVID so we had time to relax in this corner of the state. The house was easy to get to and access was off the screened in porch and helped keep the mosquitoes out. The house was very clean, spacious and stylish as photographed but you cannot photograph the amazing comfort of the beds. They made us love this place! The screened in porch was great for dinners outside. The neighbors were also nice when we walked the dog. We would recommend this place to anyone.
Stayed 4 nights in Jun 2021
Verified

10/10 Excellent

Candy S.

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

Cozy Comfortable House in the Berkshires

I've traveled to the Berkshires many times, and I loved the setting and location of this house: right across from Bartholemew's Cobble, a favorite hiking nature sanctuary. Shana was wonderful in communicating prior to and during our stay. She even left us a bottle of wine and chocolates, and other kitchen staples. The beds and furnishings were extremely comfortable. It was a rare heat wave in the area, and the one air conditioner in the house cooled off the living area extremely well, while the bedrooms were a bit warm. Most nights here will be cool, however. There were some additional lights needed in both bathrooms. We loved the screened in porch for lazing and dining. The house was a perfect cozy size for my husband and grown daughter, and close enough to Great Barrington for shopping and dining. Thanks for a great stay.
Stayed 2 nights in Jul 2019
Verified

10/10 Excellent

Debbie E.

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

Little House = Perfect Getaway

We reserved our stay at this house when we learned that our friends’ son’s wedding would be held in Sheffield. It was exactly as advertised. We wanted to invite another couple to join us, so we were looking for a place that would give each couple privacy but with enough common space to enjoy our time together. The screened-in porch off the kitchen was a major selling point. This house is well designed, well equipped, comfortably furnished, and thoughtfully arranged to anticipate every need. The property itself is on a country road, but it’s close enough to amenities like food shopping, to attractions in Great Barrington and Stockbridge, and there are even two attractions of interest right in Sheffield — Bartholomew’s Cobble (a nature preserve) and the historical display at the Ashley House. The check-in and check-out procedures are problem-free and well explained.
Stayed 5 nights in May 2022
Verified

10/10 Excellent

ant c.

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

We loved this place so much

Such a great little house and the hosts and management were superb with everything, thank you for an amazing stay and can't wait to get back there one day.
Stayed 63 nights in Jan 2022
Verified

10/10 Excellent

Amanda S.

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

Perfect fall girls getaway!

Lovely girls trip for 6. The house was tidy and clean with plenty of room to mingle & sleep. We loved utilizing the screened in porch, especially to enjoy the fall crisp air without the bugs! Will definitely return again if I’m every back in the Sheffield/ Great Barrington area!
Stayed 2 nights in Oct 2021
Verified

10/10 Excellent

Thomas H.

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

House in Sheffield

We were attending my nephew’s wedding in nearby Lakeville, CT. The house was in a beautiful location. We felt fortunate to spend the weekend in such a nice place.
Stayed 2 nights in Sep 2021

About the host

Hosted by Evergreen Home

Host profile image
EVERGREEN HOME VACATION RENTALS is a locally owned and operated company with a focus on concierge vacation rental services.
Our team's passion is working with people to create beautiful spaces to be enjoyed for an extended stay or just for a quick getaway. We believe in hard work, open communication and a hands on approach to business. Our team of hosts include Shana, Molly, and Ari and we are ready to help you plan and enjoy your next vacation or work trip. Thanks for checking out our listings, we'd love to invite you to stay!!

Why they chose this property

Lilla and Andrew live in Sonoma, California, but have a love for the Berkshires having resided here years ago. They own a bookstore in Sonoma and when house shopping this past fall they came upon this property. It reminded them fondly of the sweet home featured in The Little House, a children's book written by Virginia Lee Burton. They were smitten and the rest is history! They are so very happy to share their lovely home with guests to enjoy.

Languages:

English

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