Entire home

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

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Where to?

Dates

August 2025

September 2025

Overview
Amenities
Policies
Location
Host

Entire home

5 bedrooms2 bathroomsSleeps 103000 sq ft

Popular amenities

Dryer
Washer
Barbecue grill
Fireplace
Pet friendly
Parking available

Explore the area

Chester, VT

Okemo Mountain Resort
‪22 min drive‬
Fox Run Golf Course
‪23 min drive‬
Lake Rescue
‪27 min drive‬
Springfield, VT (VSF-Hartness State)

Room options

About the neighborhood

Chester

This vacation home is located within a 15-minute drive of Fletcher Farm School for the Arts and Crafts and Phineas Gage Memorial. The vacation home includes a kitchen, a fireplace, and a furnished balcony.

View more Vacation Homes in Chester

What's nearby

Okemo Mountain Resort - 22 min drive - 9.3 miles
Fox Run Golf Course - 23 min drive - 10.4 miles
Lake Rescue - 27 min drive - 12.6 miles
Buttermilk Falls - 27 min drive - 12.4 miles
Magic Mountain Ski Resort - 43 min drive - 24.6 miles

Getting around

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

Restaurants

‪Goodman's American Pie - ‬15 min drive
‪DJ'S Restaurant - ‬16 min drive
‪Tom's Loft Tavern - ‬18 min drive
‪Stemwinder - ‬17 min drive
‪Southern Pie Cafe - ‬17 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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
- Must be at least 28 years old to book
- 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

The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a furnished balcony or patio, and there's space to spread out with 5 bedrooms. Guests can expect to find a TV with a DVD player. Other standard amenities include a washing machine, a fireplace, and a sofa bed.

Property manager

Evolve Vacation Rental Network

Languages

English, French, German, Spanish

Similar properties

Kitchen
Washer
Dryer
Pet friendly

Property amenities

Internet

Available in the house: Internet access

Parking and transportation

Car recommended
Parking on site

Kitchen

Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Ice maker
Microwave
Refrigerator
Spices
Stovetop
Toaster

Bedrooms

5 bedrooms
Bedsheets provided
Sofa bed

Bathroom

2 bathrooms
Hair dryer
Towels provided

Living spaces

Fireplace

Entertainment

Books
DVD player
Library
TV

Outdoor areas

Barbecue grill
Firepit
Furnished patio
Yard

Laundry

Laundry facilities
Washing machine

Comfort

Air conditioning
Heating

Pets

Pet friendly

Suitability/Accessibility

Smoking not allowed

Services and conveniences

Phone

Things to do

Hiking/biking trails nearby
Hunting 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

General

Unit size: 3,000 square feet

Policies

Check-in

Check-in time starts at 3:00 PM

Minimum check-in age: 28

Check-out

Check-out before 11:00 AM

Special check-in instructions

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

Pets

This property welcomes pets
Service animals exempt from fees

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 and a first aid kit

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

Check-in: 3:00 PM
Check-out: 11:00 AM
Minimum check-in age: 28

We should mention

Details about charges, deposits, or other important information:

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
Onsite parties or group events are strictly prohibited.
Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit.

Property is also known as

Chester Farmhouse on 100 Acres, 15 Min to Okemo! Chester

404693

Frequently asked questions

What's there to do around this vacation home?

This vacation home is located in Chester, close to Okemo Mountain Resort, Fox Run Golf Course, and Dorsey Park. You'll also find DaVallia Art & Accents and South Face Express Ski Lift nearby.

Is there parking available at this vacation home?

No, this vacation home doesn't offer parking.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

What do couples enjoy most about Chester Farmhouse on 100 Acres, 15 Min to Okemo!?

Couples staying at this vacation home will appreciate amenities like a fireplace and a kitchen as well as a firepit.

Does Chester Farmhouse on 100 Acres, 15 Min to Okemo! have a hot tub?

No, this vacation home doesn't have a spa tub.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

Although pets can't stay for free, they are welcome at this vacation home.

Does this vacation home have connecting rooms?

No, there aren't connecting rooms at this vacation home.

How close is the airport from this vacation home?

The closest major airport to this vacation home is Springfield, VT (VSF-Hartness State), which is 9.2 mi away (19 minutes by car). Another top airport is Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 26.4 mi away (43-minute drive).

Are there rooms with balconies at Chester Farmhouse on 100 Acres, 15 Min to Okemo!?

Yes, every accommodation at Chester Farmhouse on 100 Acres, 15 Min to Okemo! comes with a furnished balcony with some featuring mountain views.

Chester Farmhouse on 100 Acres, 15 Min to Okemo! Reviews

9.8

Exceptional

8.6/10

Cleanliness

10/10 Excellent

Thomas C.

Jul 15, 2025

Liked: Cleanliness

Stayed 2 nights in Jun 2025

10/10 Excellent

Sarah L.

Apr 15, 2025

Liked: Cleanliness

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.

Dec 29, 2024

Liked: Cleanliness

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.

Jul 29, 2024

Liked: Cleanliness

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

Eric M.

Jul 2, 2024

Liked: Cleanliness

Wonderful

Super cool property and great hosts

Stayed 5 nights in Jun 2024

10/10 Excellent

Thomas W., Warwick, RI

Oct 21, 2022

Liked: Cleanliness

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.

Jul 30, 2022

Liked: Cleanliness

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

10/10 Excellent

Michael R.

Oct 19, 2020

Liked: Cleanliness

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

Aug 20, 2020

Liked: Cleanliness

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

10/10 Excellent

Erin C.

Mar 23, 2020

Liked: Cleanliness

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.

Mar 13, 2020

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

Jan 30, 2020

Liked: Cleanliness

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.

Jan 30, 2020

Liked: Cleanliness

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.

Jan 17, 2020

Liked: Cleanliness

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

Sep 10, 2019

Liked: Cleanliness

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

Sep 3, 2019

Liked: Cleanliness

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.

Aug 5, 2019

Disliked: Cleanliness

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.

Apr 9, 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

Stayed 2 nights in Mar 2019

8/10 Good

Pat L.

Feb 24, 2019

Cozy

Great time had by all

Stayed 4 nights in Feb 2019

10/10 Excellent

Mike (Cheuk) L.

Jan 23, 2019

Inviting and Spacious

The Chester House is fully equip to house my whole party with no issues. Rooms are spacious and clean. House is fully heated. Porch / Mud room was able to hold all our ski and snowboards. Will definitely rent again if this house is available for Okemo!

Stayed 2 nights in Jan 2019

10/10 Excellent

Mike D.

Dec 31, 2018

The house is charming, rustic, spacious, and warm. Property was picturesque!

We stayed in the Smokeshire Farmhouse this Christmas, and the experience was everything we has hoped it would be and more. There were 8 adults and 6 children in our group, and there was plenty of space in the house for everyone to eat, sleep and relax comfortably. The house has a charming, rustic feel, and was fully equipped with everything you could possibly need during your stay. The property was amazing. The kids enjoyed skating on the pond, sledding down the hill, hiking in the woods, and interacting with the animals, especially Clark the horse who is quite friendly, and the farmers dogs. The property is picturesque and completely secluded! We really enjoyed our stay, and look forward to visiting again!

Stayed 4 nights in Dec 2018

10/10 Excellent

chitra r.

Sep 10, 2018

Wonderful place for families

We loved staying in this charming, idiosyncratic farmhouse. It was the perfect place for 4 families with kids. Some of us explored the wider region, some of us just explored the hillside, the farm itself, and the stream down the hill - all of us were happy. The house is comfortable, the kitchen is a pleasure to cook in, the views and atmosphere are wonderful and make it such a retreat from everything. Donna was so helpful and communicative. We hope to come again!

Stayed 3 nights in Aug 2018

10/10 Excellent

MAHIT B.

Aug 28, 2018

Beautiful property

Stayed here with 3 other couples. Nice big bedrooms. Ample of space for everyone. Amazing grill and fire pit in the back. You wake up to Green pastures with sheep and horses ! The owners were super awesome and let us eat fresh raspberries and blueberries right from the bushes. Highly recommend it.

Stayed 2 nights in Aug 2018

10/10 Excellent

Shankari Swetaambari A.

Jul 31, 2018

Great value for money !

Beautiful farm with lots of activities. Wonderful hosts !

Stayed 2 nights in Jul 2018

10/10 Excellent

Peter C.

Mar 15, 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

Stayed 2 nights in Mar 2018