Little House, set back from the road with several acres of woods behind and a wildlife preserve across the way, offers a cozy retreat in the heart of Sheffield. Explore beautiful houses from the 1700's that overlook gorgeous views of Berkshire Hills or unwind in this charming home with an enclosed sun porch and fire pit.
Reviews
1010 out of 10
Exceptional
Entire home
2 bedrooms2 bathroomsSleeps 691 sq m
Popular amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free Wi-Fi
Air-conditioning
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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.
Property amenities
Internet
Available in the house: Free WiFi
Parking and transport
Parking on site
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Kitchen island
Microwave
Oven
Refrigerator
Toaster
Dining
Dining table
Bedrooms
2 bedrooms
Bedsheets provided
Sofa bed
Bathroom
2 bathrooms
Bathtub
Hair dryer
Towels provided
Living spaces
Dining table
Entertainment
Books
Games
Smart TV with cable/satellite channels
Outdoor areas
Barbecue grill
Garden
Patio
Laundry
Laundry facilities
Washing machine
Work spaces
Desk
Desk chair
Office
Comfort
Air conditioning
Heating
Pets
Pet friendly
Welcoming dogs only
Up to 9 kg per pet
Suitability/Accessibility
Smoke-free property
Services and conveniences
Iron/ironing board
Location highlights
In a rural location
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
-No Smoking or vaping
-No parties or events on the property
-No commercial photography or filming allowed without prior authorization
Pets
Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total (up to 9 kg per pet)
Children and extra beds
Children are welcome
Events
No events 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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number C0127342670
About the area
Located in Sheffield, this holiday 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. Visit our Sheffield travel guide
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 9 kg per pet.
How much is parking at Little House in the Woods by Evergreen Home?
On-site 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?
Checkout is at 11:00 AM.
Where is Little House in the Woods by Evergreen Home located?
Situated in a rural location, this holiday home is within 1 mile (2 km) of Housatonic River and Bartholomew's Cobble. Ashley House and Lime Kiln Farm Wildlife Sanctuary are also within 2 miles (3 km).
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Little House in the Woods by Evergreen Home Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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!
Alysa G.
Stayed 6 nights in Jun 2024
Verified
10/10 Excellent
Patricia
27 Sept 2025
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!
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!!
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!
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!
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!
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.
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.
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
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.
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.
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.
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.
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!
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.