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Cheerful 3-bedroom cottage with woodstove

Vacation home in Sheffield with kitchen and patio

Photo gallery for Cheerful 3-bedroom cottage with woodstove

Property grounds
Smart TV, fireplace, books, computer monitors
Fridge, microwave, oven, stovetop
Property grounds
Dining
Berkshire Woods Retreat offers a serene escape for the whole family. Gather around the woodstove, cook up a storm in the fully-equipped kitchen, or fire up the barbecue on the spacious deck. Take advantage of badminton in your own yard and enjoy easy access to Butternut or Catamount ski hills.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 8

Popular amenities

  • Parking available
  • Pet friendly
  • Dryer
  • Gym
  • Barbecue grill
  • Washer
The current price is AED 724
AED 1,657 total
includes taxes & fees
16 Nov - 17 Nov

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.

Cheerful 3-bedroom cottage with woodstove

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Property amenities

Ski

  • Cross-country skiing nearby
  • Snowboarding nearby

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Wood stove

Entertainment

  • Books
  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Garden
  • Outdoor furniture
  • Patio
  • Yard

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Computer monitor
  • Desk
  • Desk chair
  • Printer

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • In a rural location
  • Near a hospital

Things to do

  • Gym
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Sledding nearby
  • Swimming nearby
  • Wildlife walks nearby

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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden

Similar properties

Fridge, microwave, oven, stovetop
Great Barrington Get Away
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
9.4 out of 10, Exceptional, 25 reviews
The price is AED 1,047
AED 1,904 total
includes taxes & fees
26 Nov - 27 Nov
Great Barrington Get Away

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total (up to 50 lbs 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
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
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 C0342902670

About the neighborhood

Map
Sheffield, MA

What's nearby

  • Lime Kiln Farm Wildlife Sanctuary - 5 min drive - 2.2 km
  • Catamount Ski Area - 18 min drive - 17.7 km
  • Ski Butternut - 24 min drive - 21.6 km
  • National Shrine of the Divine Mercy - 33 min drive - 31.1 km
  • Tanglewood Music Center - 42 min drive - 42.7 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬14 min drive
  • ‪Dunkin' - ‬14 min drive
  • ‪Café Rena - ‬14 min drive
  • ‪ILSE Coffee - ‬13 min drive
  • ‪Guido’s Kitchen - ‬14 min drive

Frequently asked questions

Is Cheerful 3-bedroom cottage with woodstove pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 50 lbs per pet.

How much does it cost to stay at Cheerful 3-bedroom cottage with woodstove?

As of 14 November 2025, prices found for a 1-night stay for 2 adults at Cheerful 3-bedroom cottage with woodstove on 16 November 2025 start from $404.27, 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 Cheerful 3-bedroom cottage with woodstove?

Check-in begins at 3:00 PM.

What time is check-out at Cheerful 3-bedroom cottage with woodstove?

Check-out is at 11:00 AM.

Where is Cheerful 3-bedroom cottage with woodstove located?

Situated in a rural location, this vacation home is within 2 mi (3 km) of Lime Kiln Farm Wildlife Sanctuary, Drury Preserve, and Housatonic River. Thom Reed UFO Monument Park and Magnolia Bluffs Casino are also within 6 mi (10 km).

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Cheerful 3-bedroom cottage with woodstove Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 37 out of 40 reviews
Rating 8 - Good. 3 out of 40 reviews
Rating 6 - Okay. 0 out of 40 reviews
Rating 4 - Poor. 0 out of 40 reviews
Rating 2 - Terrible. 0 out of 40 reviews

9.8/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Eco-friendliness

Reviews

10/10 Excellent

lisa s.

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

lovely home

we had a wonderful time staying at the house, very comfortable and well equipped and responsive host.
Stayed 5 nights in Jul 2023

10/10 Excellent

Burt H.

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

Lovely Stay

We so enjoyed our three day stay at the cottage. It was incredibly well appointed, clean and so comfortable! We were in the area for a family wedding, so we didnt fully utilize all that the cottage offered, but loved all of the time we did spend there. We had some very pretty walks in the mornings with our little pup. We'd love to return at some point!
Stayed 3 nights in Dec 2024

10/10 Excellent

Cameron B.

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

A charming stay for a family

We’ve stayed a couple times now at Sabrina’s cottage in Sheffield. It’s the perfect location to being able to access Catamount Mountain for our winter trips! Only pray for more snow so we can have more fires.
Stayed 2 nights in Feb 2023

8/10 Good

Beth A.

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

Nice house in a good lication

This was a very nice, private house close to the Berkshire towns we wanted to visit. Big master bedroom and very nice master bath. I wish we had seen the stairs to the upstairs bedrooms before we booked as the were very difficult for our senior dog.
Stayed 3 nights in Oct 2024

10/10 Excellent

Catherine W.

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

Amazing property!

Sabrina saw to everything. The house even came equipped with a spice drawer, games like badminton equipment, a kid’s bedroom with games and books, and nice touches like vases of flowers. Our family was amazed and impressed. The outdoor area in the front (and back) was big enough for our grandchildren to play badminton. We very highly recommend this place!
Stayed 2 nights in Oct 2024

10/10 Excellent

Carol T K.

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

Peaceful getaway

Home is located on a quiet wooded road, perfect for a getaway with friends. There are six chairs around the large kitchen table where we gathered for eating and chatting each evening. Very comfortable for our group of five with three bedrooms upstairs (King/Queen/Bunk beds), with additional options for sleeping on main floor downstairs. We would be happy to stay here again if our travels bring us back to this area of Massachusetts!
Stayed 2 nights in Dec 2023

10/10 Excellent

Rich M.

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

Thank you

Thank you.
Stayed 1 night in Jul 2024

10/10 Excellent

Verified traveler

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

Wonderful Home-Away-From-Home in Sheffield!

We spent ten days in this charming home in Sheffield and just loved it! The house is very comfortable, is beautifully decorated in what I would call a “Boho Farmhouse” style, and the fabulous open kitchen is the best-stocked I’ve seen! There is kitchen island seating in addition to the dining table, and also two comfy lounge areas on the first floor. The wonderful, large deck has both dining and lounge areas, and there’s a magical fire pit with Adirondack chairs at the edge of the lovely back yard. Upstairs is a king master suite with huge bath; also two more bedrooms (one for kids) and a second full bath. We had three sets of guests stay with us during our time at the house, and all were very comfortable. Sabrina has thought of everything, and responded quickly to our few questions. We had a wonderful time and will be back!
Stayed 10 nights in Oct 2023

10/10 Excellent

Sami S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house was perfect for us - and exactly as described in the VRBO description. It was really well-appointed, particularly the kitchen. But the little details were great - the products in the bathroom, etc. It just made for a very easy, enjoyable stay. Sabrina is also really responsive. There was a WiFi issue the night we arrived, outside of their control. She kept us posted as she heard from the provider and even gave us a small reimbursement for our inconvenience. I really found that above and beyond - and appreciated.
Stayed 2 nights in Jul 2025

10/10 Excellent

Sarah W.

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

Cozy stay

We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time.
Stayed 1 night in May 2025

10/10 Excellent

Colleen L.

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

Fantastic Stay in the Berkshires

Cute house that was perfectly arranged for our family. Kitchen is well stocked with spices galore! We cooked at home every night. Went hiking in both NY, CT and MA - super easy to get to all locations, beautiful views of mountains all around. Will definitely come back to this house again with our family!
Stayed 3 nights in Apr 2025

10/10 Excellent

Kelly R.

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

Great place!

The property was centrally located for skiing, and was a comfortable stay.
Stayed 3 nights in Dec 2024

10/10 Excellent

John G.

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

Second Stay

We stayed at this home about the same time last year and we were so happy with everything about it, we jumped at the opportunity to stay there again. The house has absolutely everything you'd need and is close to Canaan, CT and Great Barrington, MA and everything the Bershires have to offer. Sabrina is a great host and responded within minutes to any questions I had. We HIGHLY recommend this home.
Stayed 3 nights in Dec 2024

10/10 Excellent

Lisa

Liked: Cleanliness, amenities, property conditions & facilities, communication
Delightful home in very quiet neighborhood near hiking trails. House had every amenity you might need (except tissues). Less than 20 minutes drive from Sheffield. Great restaurants in town. We very much enjoyed our stay in this house in the country and would highly recommend it to anyone wanting to stay in the area.
Stayed 3 nights in Nov 2024

10/10 Excellent

Verified traveler

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

Another wonderful stay in Sheffield!

We just rented this super charming house for the second time, and again had such a lovely stay that we're already planning next year's visit! Sabrina is a terrific host, very responsive and thoughtful. The microwave gave out during our stay; she had a replacement there the next day! We love the quiet yet convenient location in Sheffield, and this year were pleased to find we could walk from the house to the quiet gravel roads that wind through the countryside. As mentioned by all, the very well stocked kitchen is the heart of this house's wonderful first floor living area. Love, love the deck, especially the lounge area for cocktail hour, and enjoyed playing badminton in the yard! 5 stars! We will be back!
Stayed 14 nights in Sep 2024

10/10 Excellent

Lois

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

Amazing!

Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath.
Stayed 33 nights in Aug 2024

10/10 Excellent

Kenneth B.

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

Short stay

As advertised! Would definitely stay there again!
Stayed 1 night in Jul 2024

10/10 Excellent

Lance G.

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

AT Hike Base

This home was "as advertised" - plenty of room. Nice neighborhood setting. Well stocked kitchen & nice outside area in the backyard / deck. We used it as a base camp for section hiking the appalachian trail.
Stayed 4 nights in May 2024

10/10 Excellent

Alison B.

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

Neat and comfortable house with great landlord

We rented for the winter to use on the weekends. Sabrina was very responsive and thoughtful throughout. The house is incredibly well stocked and thoughtfully organized. Two seating areas downstairs made it easy for our family of four to spread out, even when we had guests. Kitchen is well laid out, mattresses are very comfortable, and the surrounding area is quiet. We would definitely go back.
Stayed 59 nights in Jan 2024

10/10 Excellent

John G., Eliot, ME

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

Fantastic Home

To a person, we wanted for nothing during our stay. House had everything we could possibly need on vacation. Quiet road, close to Canaan CT and Great Barrington MA, comfortable beds, large kitchen, big bedrooms, room to gather together. Not a single complaint. We'd absolutely stay here again and if its available next year, we will!
Stayed 4 nights in Nov 2023

10/10 Excellent

Matthew L.

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

Perfect Vacation Home in Amazing Location

Stayed here with my family and it exceeded our expectations. Everything in the listing was spot on. We especially appreciated the fully stocked kitchen which made meal prep fun and easy. Loved the views off the back deck into the deep woods. Beds were comfy and bathrooms were working great and fully stocked. Very quiet and private location and just a stone's throw to little Sheffield which was very quaint (must try Roberto's for pizza/salads) and just a few minutes further to Great Barrington which was a wonderful artsy town with great food and shopping. All around a very memorable stay.
Stayed 3 nights in Oct 2023

10/10 Excellent

Kim A.

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

Beautiful and comfortable home!

We stayed at this property for a weekend wedding at Gedney Farm The house is well equipped and comfortable. Would definitely recommend!
Stayed 2 nights in Sep 2023

10/10 Excellent

Thomas H.

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

Enjoyable Berkshires getaway

This home was a perfect place for a family reunion.
Stayed 2 nights in Sep 2023

10/10 Excellent

Stefan K.

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

Great stay

We were in the area for a project and the house fit the bill. 5 stars across the board. i can't wait to stay again. thanks for the stay.
Stayed 2 nights in Sep 2023

8/10 Good

William M.

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

Loved the place, but...

Great place, but it could have used an overall ‘deep cleaning’ inside and out. The property was well equipped with updated appliances, pots, pans, dishes, utensils, cutlery, linens and plenty of ice!😬 and hot H2O!!! The hostess, Sabrina, could not have been nicer or more accommodating. I would certainly do to another Vrbo rental from her and sister-in-law. It’s a perfect location for a Berkshire School reunion!👍
Stayed 3 nights in Jun 2023