Place, Fletcher Farm School for the Arts and Crafts
14 min drive
Okemo Mountain Resort
Place, Okemo Mountain Resort
19 min drive
Fox Run Golf Course
Place, Fox Run Golf Course
21 min drive
Springfield, VT (VSF-Hartness State)
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
About this property
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Welcome to 'Smokeshire Hilltop Farmhouse!' This lovely 5-bedroom, 2-bathroom vacation rental sits on a plateau above the Williams River in Chester. Located on a working farm with beautiful grounds, the rustic farmhouse offers travels the ideal escape at any time of the year! Spend your day hiking the nearby trails in the summer or skiing the slopes at Okemo in the winter. After your adventures, cozy up by the wood-burning fireplace and enjoy a peaceful evening at home.
-- THE PROPERTY --
MRT-11153470-001 | Pet Friendly w/ Fee (Dogs & Horses Only) | Furnished Sunroom | Sleigh/Carriage Rides Available
Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin Beds, Full Bed | Bedroom 5: 2 Twin Beds | Study: Sleeper Sofa
OUTDOOR SPACE: Spacious unfenced yard, outdoor dining INDOOR LIVING: Flat-screen TV, DVD player, fireplace, dining table, shower/tub combo KITCHEN: Stove/oven, microwave, dishwasher, refrigerator, dishware/flatware, toaster, spices, Keurig single-serve coffee maker, drip coffee maker, kettle, standing mixer GENERAL: Free WiFi, washer/dryer, linens/towels, central heating, mini-split A/C & heating units ACCESSIBILITY: 2-story home, stairs required, 1 bedroom on 1st floor FAQ: Pet fee (paid pre-stay), 1 exterior security camera (facing front entry), 4WD recommended in winter, homeowner on-site (private home, same property), limited cell service PARKING: Driveway (5 vehicles)
-- THE LOCATION --
WINTER REC: Okemo Mountain Resort (8 miles), Magic Mountain Ski Area (18 miles), Bromley Mountain Ski Resort (29 miles), Killington Ski Area (30 miles), Stratton Mountain Resort (32 miles), Mount Snow Grand Summit Resort (46 miles) SUMMER REC: The Fort At No 4 (17 miles), Wilgus State Park (20 miles), Mt Ascutney State Park (21 miles), Killington Ski Area (30 miles) ATTRACTIONS: Okemo State Forest (11 miles), Buttermilk Falls (11 miles), Mt Ascutney State Park (21 miles), Saint-Gaudens National Historic Park (27 miles), Pillsbury State Park (42 miles), Mt Sunapee State Park (40 miles) AIRPORTS: Lebanon Municipal Airport (40 miles), Bradley International Airport (122 miles)
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- No smoking - Pet friendly w/ $50 fee (+ fees & taxes, dogs & horses only) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The 2-story property requires using stairs to enter - NOTE: This house is located on a working farm and animals may be present during your stay - NOTE: Four-wheel drive or all-wheel drive is recommended in the winter months to access the property - NOTE: The property does have cell phone service, but it may be spotty since the property is located in a rural area. Please check with your provider to confirm your service quality. There is a landline in the property - NOTE: Your safety matters. This property features an exterior security camera located at the front door facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video and sound when motion is detected by the device - NOTE: The homeowner lives on-site, in a completely separate unit, and may be present during your stay
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
Outdoor space
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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 and a first aid kit
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 Muckross State Park and Camp Plymouth State Park. Bonnie's Bundles Dolls and DaVallia Art & Accents are also worth visiting. Make sure you don't miss outdoor adventures like hiking/biking trails and hunting.
Fletcher Farm School for the Arts and Crafts - 14 min drive - 11.3 km
Okemo Mountain Resort - 19 min drive - 14.9 km
A Ski Lift - 19 min drive - 14.9 km
Fox Run Golf Course - 21 min drive - 16.7 km
Lake Rescue - 23 min drive - 20.6 km
Getting around
Bellows Falls Station - 36 min drive
Springfield, VT (VSF-Hartness State) - 19 min drive
Restaurants
The Loft Tavern - 19 min drive
MacLaomainn's Scottish Pub - 16 min drive
Dunkin' - 16 min drive
The Waffle Cabin - 22 min drive
Goodman's American Pie - 17 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 does it cost to stay at Chester Farmhouse on 100 Acres, 15 Min to Okemo!?
As of 3 Apr 2026, prices found for a 1-night stay for 2 adults at Chester Farmhouse on 100 Acres, 15 Min to Okemo! on 2 June 2026 start from AU$340, 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 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.
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
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!
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.
Robert M.
Stayed 3 nights in Jul 2024
Verified
10/10 Excellent
Peter C.
15 Mar 2018
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
Peter C.
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
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.
Zina G.
Stayed 6 nights in Jul 2025
Archival
10/10 Excellent
Derek S.
31 Aug 2017
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!
Derek S.
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
Jacob
27 Dec 2022
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.
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.
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!
Ben l.
Stayed 6 nights in Jul 2022
From a partner site
10/10 Excellent
mary
29 June 2021
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.
mary
From a partner site
10/10 Excellent
mary
1 Apr 2021
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.
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!!
Dawn F.
Stayed 6 nights in Jul 2020
From a partner site
10/10 Excellent
Bharti
11 Aug 2020
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.
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 ;)
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.
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!
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.
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.
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.
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.
Octavian B.
Stayed 3 nights in Aug 2019
Verified
2/10 Terrible
Steven A.
5 Aug 2019
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.
Steven A.
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
10/10 Excellent
Ed B.
9 Apr 2019
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
Ed B.
Stayed 2 nights in Mar 2019
Verified
10/10 Excellent
Sara D.
5 Mar 2019
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!