See all properties
Entire home

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

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

Chester Vacation Rental | 5BR | 2BA | Stairs Required | 3,000 Sq Ft
Backyard
Living Room | Central Heating | Free WiFi
Living area
Dining Area | Dishware & Flatware

Reviews

9.8 out of 10, Loved by Guests
Top 10% based on
5 bedrooms2 bathroomsSleeps 103000 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning
  • Outdoor space

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
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
Outdoor space

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Winter Street view
Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
10.0 out of 10, Exceptional, (16 reviews)
Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!

House Rules

Check in after 3:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

Pets allowed
default

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

We should mention

A car is recommended for transport to and from this property

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.
View more Holiday homes in ChesterOpens in a new window
Map
Chester, VT

What's nearby

  • Fletcher Farm School for the Arts and Crafts - 14 min drive - 11.3 km
  • Dorsey Park - 17 min drive - 13.8 km
  • DaVallia Art & Accents - 18 min drive - 14.8 km
  • Okemo Mountain Resort - 19 min drive - 14.9 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 5 Mar 2026, prices found for a 1-night stay for 2 adults at Chester Farmhouse on 100 Acres, 15 Min to Okemo! on 2 Jun 2026 start from £176, 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, Okemo Mountain Resort and Fletcher Farm School for the Arts and Crafts. Bonnie's Bundles Dolls and DaVallia Art & Accents 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

10/10 Excellent

Eric M.

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

Wonderful

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

10/10 Excellent

Sarah L.

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

10/10 Excellent

C W.

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

10/10 Excellent

Robert M.

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

10/10 Excellent

Peter C.

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

10/10 Excellent

Zina G.

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
This review was submitted before 2018 and can't be verified.

10/10 Excellent

Derek S., Charlestown, MA

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!
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Jacob

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.

10/10 Excellent

Thomas W., Warwick, RI

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

10/10 Excellent

Ben l.

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
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

mary

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.
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

mary

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.

10/10 Excellent

Michael R.

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

10/10 Excellent

Dawn F., Chalfont PA USA

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
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Bharti

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.

10/10 Excellent

Erin C.

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 ;)

10/10 Excellent

mary R.

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

10/10 Excellent

Gina B., Plaistow, NH

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!

10/10 Excellent

Steven B.

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.

10/10 Excellent

Lynne M.

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

10/10 Excellent

Donna L., Pelham

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

10/10 Excellent

Octavian B., Montreal

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

2/10 Terrible

Steven A.

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

10/10 Excellent

Ed B.

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

10/10 Excellent

Sara D.

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!

About the host

Hosted by Evolve Vacation Rental Network

Host profile image

Languages:

English, French, German, Spanish
Tell us how we can improve our siteShare feedback

Hotels

Holiday Rentals