Chester Farmhouse on 100 Acres, 15 Min to Okemo!

Photo gallery for Chester Farmhouse on 100 Acres, 15 Min to Okemo!

A rustic cabin with a large barn, surrounded by a pond and dense forest.
A patio with a table and chairs, surrounded by a grassy area and trees, with a mountain in the background.
A cozy living room with a fireplace, wooden walls, a sofa, and a coffee table.
A cozy living room with a fireplace, leather sofa, wooden furniture, and a large window with curtains.
A dining area with a wooden table and chairs, a fireplace, and a cozy living room with a red sofa and a television.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Spacious, comfortable rooms
    Guests love the top-rated, generously-sized rooms.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Furnished balcony or patio
  • Barbecue grill
  • Air-conditioning
  • Pet-friendly
  • Refrigerator
  • Internet

Explore the area

View in a map
Chester, VT
  • Place, Fletcher Farm School for the Arts and Crafts
    ‪15 min drive‬
  • Place, Dorsey Park
    ‪18 min drive‬
  • Place, Okemo Mountain Resort
    ‪21 min drive‬
  • Airport, Springfield, VT (VSF-Hartness State)
    ‪19 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Additional Sleeping (Study)

1 Double Sofa Bed

Bedroom 1

1 Queen Bed

Bedroom 2

1 Double Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Single Beds and 1 Double Bed

Bedroom 5

2 Single Beds

2 bathrooms

Full Bathroom

Full Bathroom

Spaces

Deck or patio
Kitchen

Add dates for prices

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About the area

Chester

Chester is home to this holiday home. Phineas Gage Memorial and Eureka Schoolhouse are local landmarks, and the area's natural beauty can be seen at Green Mountain National Forest and Muckross State Park. Bonnie's Bundles Dolls and DaVallia Art & Accents are also worth visiting. Make sure you don't miss outdoor adventures like hiking and hunting.
View more Holiday homes in ChesterOpens in a new window
Map
Chester, VT

What's nearby

  • Fletcher Farm School for the Arts and Crafts - 15 min drive - 11.3 km
  • Dorsey Park - 18 min drive - 13.8 km
  • Okemo Mountain Resort - 21 min drive - 15.3 km
  • Fox Run Golf Course - 22 min drive - 16.7 km
  • Lake Rescue - 24 min drive - 20.6 km

Getting around

  • Bellows Falls Station - 36 min drive
  • Springfield, VT (VSF-Hartness State) - 19 min drive

Restaurants

  • ‪Southern Pie Cafe - ‬17 min drive
  • ‪MacLaomainn's Scottish Pub - ‬16 min drive
  • ‪Dunkin' - ‬16 min drive
  • ‪The Hatchery - ‬16 min drive
  • ‪The Loft Tavern - ‬19 min drive

Frequently asked questions

Is Chester Farmhouse on 100 Acres, 15 Min to Okemo! pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Chester Farmhouse on 100 Acres, 15 Min to Okemo!?

On-site parking is available at the property.

What time is check-in at Chester Farmhouse on 100 Acres, 15 Min to Okemo!?

Check-in begins at 3:00 PM.

What time is check-out at Chester Farmhouse on 100 Acres, 15 Min to Okemo!?

Checkout is at 11:00 AM.

Where is Chester Farmhouse on 100 Acres, 15 Min to Okemo! located?

Situated in Chester, this holiday home is within 9 miles (15 km) of Phineas Gage Memorial, Fletcher Farm School for the Arts and Crafts and Bonnie's Bundles Dolls. DaVallia Art & Accents and Dorsey Park are also within 9 miles (15 km).

Reviews

9.8

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. 45 out of 51 reviews
Rating 8 - Good. 5 out of 51 reviews
Rating 6 - Okay. 0 out of 51 reviews
Rating 4 - Poor. 0 out of 51 reviews
Rating 2 - Terrible. 1 out of 51 reviews

8.8/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.6/10

Location

9.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Wonderful

Super cool property and great hosts
Stayed 5 nights in Jun 2024
Verified review

10/10 Excellent

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

Smokeshire Farm July 2024

Lovely house on beautiful property. We thoroughly enjoyed staying at Smokeshire Farm. We will never forget the moon rising over the hill or being greeted by the sheep in the morning.
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

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

Great for reconnecting with friends

The farmhouse was the perfect spot for old friends with new little to reconnect. Great space for big meals, the living room was great for us to chat and let the toddlers play. Our hosts were awesome and shared their lambs and foal with us! The property was just stunning
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

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

We loved it!

Charming is the key word for this place! From the huge stone fireplace, to the solid wood, exposed beams, to the spacious bedrooms, to the portrait-like, snow-covered surroundings complete with horses and a barn, our family of 8, including 2 grandkids, loved our time at the Chester, VT Farmhouse. We hope to return someday!
Stayed 4 nights in Dec 2024
Verified review

10/10 Excellent

Great Weekend getaway for three generations!

Plenty of room and amenities for grandparents, three adult children and three grandkid skiers!! Almost had to cancel due to wicked NorEaster coming in on Friday, but we made it here and so glad we did on Friday! The working farm is classic Vermont, the hill off the pond was perfect for sledding and the slopes are 20 minutes away. The owners were away, but the caretakers stopped by to check in on us. All you need to do is bring your food and libations, the rest is here! Highly recommend to all! Thanks! Looking forward to next year! Peter and Karin Conopask, Rhode Island
Stayed 2 nights in Mar 2018
Response from VrboOwner on 27 Mar, 2020
Thanks guys! Sorry we didn't get to meet you, we got stuck by the Nor'easter down south (so, not too bad) and didn't get back until late on Sunday. Hope to see you back! Donna
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our family had a wonderful experience at the farm. Donna and Pete were lovely hosts who live just up the next driveway. There was plenty of room for our family of seven to spread out. We saw the horses and sheep. We picked blueberries. We played in the river and saw many tadpoles and frogs. The books in the study were excellent. Many were older. If you are a literature or history buff, this is the room to stay in. We were given plenty of linens and dishes. This is a much older house so just be aware of the uneven floor. Loved that there was air conditioning which we usually don’t have in a rural vacation rental. There’s a hutch at the base of the road where you can buy maple syrup. You can walk up another road and see where the trees are tapped. There’s also an old (1800s) cemetery you can visit. We didn’t really do anything but stay within short distance of the house. The Shaw’s is only a 15 min drive. Cell coverage is spotty but WiFi is good.
The study. My husband spent lots of time here. Great old books.
Books in the study.
Blueberries were ripe for picking in late July.
The river on the property, quarter mile from the house.
Stayed 6 nights in Jul 2025
Archival

10/10 Excellent

Magical Vermont Farmhouse!

Wow! This place is absolutely charming and a real gem! The house is big yet cozy and comfortably slept 12 adults and accommodated us all sitting together for large family style meals. The property is incredible, you will feel totally secluded up in the mountains surrounded by beautiful forests, fields, a pond and stream. Our group enjoyed waking up to look out on the lovely mountain view while sipping our coffee, read ing and practicing yoga in the backyard. During the day we explored the surrounding forest, hiked up the creek and took a dip. What really made our stay enchanting were all the amazing animals on the property. Two gorgeous and extremely friendly horses roamed the property and let us pet them while they grazed. We loved watching all the sheep and particularly loved feeding the baby pigs. There are blue berries and raspberries on the property which we were able to pick as well. In the evenings our group enjoyed sitting around the large outdoor fire pit with plenty of chairs for fireside chats under the stars. Donna and her husband are extremely friendly, generous, and lovely hosts! We couldn't have enjoyed our stay more and are looking forward to returning back to this amazing Vermont getaway in the future!
Response from VrboOwner on 27 Mar, 2020
Thanks Derek, it was great to have your group! We enjoyed sharing our farm with you all, and you're welcome back any time! Donna
From a partner site

10/10 Excellent

An Honest Review

Coming from a background of rural living, farming, and dealing with honest people, I think I’m fit for leaving an honest review. Our stay was first met with challenges that could not be controlled by anyone. Weather delayed our stay by a whole day, but Donna was kind enough to refund 2 nights. (Was not requested by us) this was nice due to unseen costs we had to pay to stay somewhere else. Once at the house, it was wonderful. I could tell instantly that one side of the house was extremely old. (Early 1800’s) This was great to see such a cool piece of history of old Vermont. If you’re looking for a beautiful rustic farmhouse to stay with plenty of room and great price? This is it. The house was comfortably cool the entire stay, but that forced everyone to spend quality time in the living room near the fire place. But even this was not the highlight of my stay, personally. Donna, the owner is what made me happy choosing to stay at their home in Chester. Communication was excellent, seeing work horses being worked in the field was also great to see. Got to spend time in some poor weather speaking with Donna as well. 10/10 I would recommend to a friend and will also be returning in the future for winter ski trips.
Verified review

10/10 Excellent

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

Very relaxing

It is definitely somewhat isolated but the fact that it was a working farm with horses and sheep was such a thrill for our grandkids (age 6-10). They loved feeding the horses and interacting with the owners. Sitting around the fire pit was relaxing for the adults. We were three generations and had a wonderful time interacting and enjoying seeing the children have such a good time. Our family dog seemed to like the farm atmosphere as well. Donna and Peter were wonderful hosts. We hope to go back some day.
Stayed 3 nights in Oct 2022
Verified review

10/10 Excellent

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

Awesome stay!!

Fantastic. Very peaceful. Loved seeing the horses and sheep in the distance. Blueberry picking onsite, hiking trails out the door, kids playing in the shallow river down the hill. Echo lake and going up the chairlift at okemo were awesome. Fire pit was perfect. Attentive and friendly host. Overall we absolutely loved our stay and plan to go back!
Stayed 6 nights in Jul 2022
From a partner site

10/10 Excellent

Serene, peaceful, lovely

Donna and Peter could not be better hosts! They have the most bucolic, peace-filled setting with lambs and horses that you can see from your bed in the morning! The house is clean, comfortable, cozy, there is a very well-equipped kitchen and a fantastic patio, and firepit in the backyard. Right down the road is the Williams River, it was shallow enough for the 3year old to play in all morning. Hiking all around, farm markets, festivals, delicious berries, and the peace and quiet that calm your heart. Our family loves it here, we are always sad to go, no matter how much time we've spent on this beautiful farm. Thanks to Donna and Peter for sharing this very special place.
From a partner site

10/10 Excellent

Best winter of our lives

Our family spent the winter at the Farmhouse this year. It was magical from start to finish. Snow, sledding, skating, bonfires, sheep, horses and a lovely dog named Jen. Peter and Donna are marvelous hosts, sharing their space, their knowledge, their warmth and their kindness. Our family of 11 loves this house, loves this farm and feel truly blessed to be able to spend time in this special place. If you are lucky enough to stay here, you are lucky enough indeed.
Verified review

10/10 Excellent

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

Classic New England farmhouse

Cozy and comfortable. Beautiful property and location. Great place to bring your dogs and kids.
Stayed 4 nights in Sep 2020
Verified review

10/10 Excellent

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

Perfect get away

We had such a good time in this house. Clean, everything we needed. Donna, the owner was welcoming and came over within minutes when I let her know we ran out of propane for the grill. Fit our family of 9 perfectly. We were there during the hottest week of the summer and sleeping was comfortable since it gets cool at night. Thank you!!
Stayed 6 nights in Jul 2020
From a partner site

10/10 Excellent

Tranquil

Lovely farmhouse in southern Vermont. The home is located on a quiet and tranquil hill surrounded by barns and rolling hills with sheep, horses and pigs. No neighbors in sight (but owners are nearby and very responsive). A stream runs nearby where we swam everyday. The house itself is large with multiple rooms. It is decorated with little pieces of history. It is clean and warm and inviting. Clean and plenty of linen and comfortable pillows. We stayed in the summer and there was no AC but the entire hills is so cool and the fans were adequate. At night it can get chilly but the warm blankets were perfect. HUGE yard where we had an outdoor fire and roasted s’mores. We had a wonderful time picking blueberries. I would absolutely come back here. The owner Donna and Peter are wonderful and excellent in their communication. Lovely people.
Verified review

10/10 Excellent

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

Amazing property and hosts, scary road!

This home was charming, huge, well stocked, etc. everything was excellent, perfectly described by hosts, and wonderful...the hosts absolutely did their job in describing the 2 miles up to the house, but I did not take it seriously enough. The hill wasn’t that bad (luckily it wasn’t snowing and I have AWD), but the 1.5 mile flat windy part was a new experience in the mud, next to a river. I am admittedly a terrible driver, so I would 100% recommend this house if you’re not afraid of a little dirt road ;)
Verified review

10/10 Excellent

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

A Favorite Family Vacation

Ten of us, ranging in age from 1.5-67, stayed at the farmhouse for two weeks in February and we had the time of our lives. Sheep! Horses!Bon Fires! Fires!Sledding! Sleigh rides! Peter and Donna could not have been more accomodating, truly lovely hosts, who shared their farm with us generously and kindly. It is an old farmhouse, not particularly clean, but that was irrelevant to us, we were cozy and warm, happy to be sharing this special place, feeling as though we took a step back in time, and delighted to do so.
Stayed 14 nights in Feb 2020
Verified review

10/10 Excellent

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

Perfect house for our big family!

We had a great time at the Smokeshire property. Tons of room for the kids to play outside (loved sledding down the big hill). Close to Okemo and downtown Ludlow. The house was rustic and had a lot of history... something our family loved! Great home for a family getaway in a perfect VT setting!
Verified review

10/10 Excellent

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

Weekend away

Spent a weekend with the family there. The directions and expectations were well laid out. The place was clean and plenty of space to hang out for 7 adults and 3 kids. Beds were not the most comfortable but they made do.
Verified review

10/10 Excellent

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

Winter Heaven!

All twelve of us, ages 9 through 73, had a blast. Peter and Donna, managers, are friendly, helpful, and very responsive. Lots of great family spaces and privacy spots, too.
Stayed 4 nights in Dec 2019
Verified review

10/10 Excellent

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

Wonderful Vacation!

We had a fabulous time. It was a different type of vacation for our family and everyone loved it. There were 5 adults and 5 children ranging in age from 17-3. The electronics were at a minimum and we enjoyed each other's company and being outdoors. The grounds are beautiful and seeing the sheep, pigs and having the horses visit every evening was amazing. Our older grandchildren loved the library and the old books and history of the property that they found. This was so much better than everyone being on their phones and iPads. Donna and Peter were visible and available if needed. The house is over 200 years old and anyone booking this home needs to understand that. We just loved it! Thank you Donna, Peter, Sarah, Becky, Freole and Clark for a fabulous 4 days.
Stayed 4 nights in Aug 2019
Verified review

10/10 Excellent

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

Great, relaxing weekend

Gorgeous rustic farmhouse on a beautiful secluded property. Great for a group of friends to catch up and relax over a long week end. The large outdoor space was especially great for our active dog to run around and burn off his energy. Donna and Peter always available to answer any questions, yet respecting our privacy. Our group of 14 people enjoyed the stay very much. We most probably come back in the winter.
Stayed 3 nights in Aug 2019
Verified review

2/10 Terrible

Disliked: Cleanliness, listing accuracy

Nice location...not worth the money...Sweaty Mess

PROS: Farm atmosphere very relaxing with beautiful horses right in site. CONS: The property is in disrepair. Numerous broken windows, allowing an array of flying friends in. Worn/slippery area rugs and dirty floors. The exterior landscaping was also overgrown along the home. The listing did state there was no air conditioning but there was ample opportunity and locations for a couple of window units for emergency heat conditions. The fans provided were cheap and barely moved the 95 degree air. Lastly there is a Nest camera inside the front porch area. These cameras can here everything and there should be NO CAMERAS ANYWHERE IN THE INTERIOR OF A RENTAL!! This is a real good one to scroll right by.
Stayed 2 nights in Jul 2019
Response from VrboOwner on 27 Mar, 2020
Steven, we're sorry to hear your stay fell short of your expectations. The homeowner ordered a replacement window for the damaged one, but unfortunately, it has been on order and hadn't been delivered before your stay. The braided rug in the living room is an antique. The owner aims to keep the old farmhouse ambiance and is having it repaired. We strive to advertise our listings in the most detailed light, which is why we highlight that the farmhouse has an exterior camera that only points out towards the entrance to the porch. The owners do not have the sound on. We also don't list air-conditioning, central or individual units, as an amenity. However, we're sorry if that caught you off guard. We're sorry if the floors were dirty at all, as this is the first negative feedback that the owner has received regarding this matter. They wish you would have notified them of any issue while you were in residence so they could have addressed it promptly. The owners take pride in providing exceptional guest experiences, and as evidenced in past reviews, we're confident this home will continue to host many satisfied guests! Best, the Evolve Team
Verified review

10/10 Excellent

Enjoyable Country Farmhouse Stay

Our family had a wonderful stay at this farmhouse which had more than ample room for our group of 8 adults. The large living room with a fireplace was a great place for everyone to relax and hang out. The snow covered rolling hills of the farm were a perfect backdrop and provided some fun sledding. The owners/hosts were very thorough and detailed with information and assistance. It was a very enjoyable stay. E. Barry
Stayed 2 nights in Mar 2019
Verified review

10/10 Excellent

Great ski house for a group!

Three families stayed at this beautiful Vermont farmhouse and we had a wonderful time! There is plenty of room for all and the kids loved seeing the barn with the sheep! It was very close to Okemo and in a lovely, picturesque location. Would definitely stay here again, thank you for a great long weekend!
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