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Circa 1868 Chester Home-Less than 20 MIN TO OKEMO

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Exterior
Terrace/patio
Bathroom
Interior
Private kitchen

Reviews

10 out of 10
Exceptional
4 bedrooms2+ bathroomsSleeps 8399.5 sq m

Popular amenities

  • Gym
  • Pool
  • Dryer
  • Washer
  • Fireplace
  • Parking available

Explore the area

Map
Chester, VT
  • DaVallia Art & Accents
    ‪16 min walk‬
  • Vermont Country Store
    ‪12 min drive‬
  • Okemo Mountain Resort
    ‪22 min drive‬
  • Springfield, VT (VSF-Hartness State)
    ‪16 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Guest Room 1

1 Queen Bed

Guest Room 2

1 Queen Bed

Guest Room 3

1 Queen Bed

Guest Room 4

1 Queen Bed

2 bathrooms, 1 half bathroom

First Floor Bathroom

Bathtub or shower · Toilet

Second Floor Bathroom

Bathtub or shower · Toilet

Second Floor Half Bathroom

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Dining area

About this property

Circa 1868 Chester Home-Less than 20 MIN TO OKEMO

OVERVIEW
Our historic 1868 'Elm House' is located in the picturesque town of Chester, nestled in the heart of Chester Depot. The 'Elm House' is perfect for city dwellers looking for a country escape, traveling families, romantic getaways, retreat weekends, girls trip, holiday stays, reunions, celebrations etc;

Our beautifully appointed and spacious space will make for a relaxing and cozy getaway. The Williams River flows behind our home amongst the chestnut and apple trees.

KITCHEN
Our home has a traditional farmhouse style kitchen complete with rustic wood floors and modern amenities. We have provided everything you need to prepare your own farm-to-table dinner with fresh food from the local farmer's market or country store across the street. We also have a Keurig and french press. For your added convenience we have provided a starter supply of fresh ground coffee, creamer and assorted teas.

DINING ROOM
In the formal dining room, we have a designated bar area equipped with glassware and other bar essentials as well as a full china set for your use.

BEDROOMS
The 'Elm House' offers 4 bedrooms, each designed to provide a relaxing and cozy atmosphere. Each bedroom is furnished with memory foam queen beds. There is one bedroom and bathroom on the first floor and three guest bedrooms and 1.5 bathrooms on the second floor.

WIFI & TV
The house has WIFI and a 'Smart TV' (Netflix, Hulu, Amazon, etc. streaming for your devices).

DECK & YARD AREA
Outside, there is a large wraparound deck with rocking chairs where you can enjoy coffee or cocktails. The yard space has plenty of room for a picnic or for yard games.

MUDROOM/SKI STORAGE
There is also a large mudroom that is perfect for ski and snowboard storage.

WHAT TO DO:
In the village of Chester-enjoy quaint restaurants and taverns, antique shops, art galleries, and a country market.

Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers and breweries (near Harpoon & Long Trail)

Close proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington)

Come experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!

For Spring and Summer fun- take a hike! There are several popular hiking trails in Chester-Lost Mine Hiking Trail and Green Mountain Nature Trail. In Chester there is a town pool you can access or check out Rainbow Rock (a local swimming hole) or Buttermilk Falls in Ludlow for waterfall/swimming adventures. In Springfield there is a pick your own farm-Wellwood Orchards for strawberries, blueberries, raspberries, peaches, plums and cherries. For more outdoor adventures, bring your bikes, kayaks or golf clubs!

Fall is a time of wonder and delight in this quintessential Vermont town-perfect for leaf peeping, picnicking, apple picking, scenic train rides at Chester Depot (only footsteps away from Elm House) or enjoy the annual fall festival on the green in September.

In the Winter months, bring your ice skates, skis, snow shoes and snow boards! We are conveniently located near 5 of Vermont's finest ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington)

Anytime of the year is a great time to visit a maple sugar house, Mitch's Maples (less than a mile from our home) or the Vermont Country Store (less than 10 miles) or take a driving tour of Vermont's many covered bridges!

Be sure to check out the local dairy farm, Jersey Girls Dairy & Farm Store for fresh milk and dairy products or the nearby Farmers Markets in Ludlow and Londonderry.

For a more relaxing and rejuvenating adventure, spa services are available at Castle Hill Spa-an Aveda Concept Spa.

The Spring House Pool and Fitness Center at Okemo is another great place to unwind after a long day. Indoor pool, hot tub and fitness center.

We don't live on the property, but we have a caretaker nearby who looks after our home and can assist if needed. If an issue arises, please let us know immediately so we can solve and you can relax + enjoy your stay!

DISTANCE FROM ELM HOUSE TO:
Grafton Inn-8 miles (12.8 km)
Magic Mountain Ski Area-13 miles (20.9 km)
Okemo Mountain Resort-15 miles (24 km)
Bromley Ski Resort-22 miles (35.4 km)
Stratton Mountain Resort-26 miles (41.8 km)
Killington Resort-29 miles (46.6 km)
Woodstock, VT-31 miles (49.8 km)
Manchester, VT-31 miles (49.8 km)
Manchester-Boston Regional Airport-Manchester, NH (MHT)-93 miles (149.6)
Bradley International Airport-Hartford, CT (BDL)-114 miles (183.4 km)
Boston, MA-136 miles (218.8 km)
New York City-249 miles (400.7 km)

Please note:
**There is a glitch on VRBO showing pool, hot tub-we do not have these items, nor have them selected as an option**

Cell service is sporadic in this region of southern Vermont. Cell phone + GPS services may be limited in certain areas.

In Summer months-we have window unit AC's in the bedrooms-we do not have central air.

Property manager

Jennifer & Michael
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 3–17
Not baby proofed-Steep staircase/no baby gate
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Please note: For the protection of our property, we have 1 exterior camera that is NOT monitored.

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
On-site parties or group events are strictly prohibited
Long-term renters welcome
This property uses eco-friendly cleaning products
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, a first aid kit and a deadlock

We should mention

A car is required for transport to and from this property

About the area

Chester

Chester Depot, a neighbourhood in Chester, is home to this holiday home. Okemo Mountain Resort and Crown Point Golf Course are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Muckross State Park and Lowell Lake State Park. Travelling with kids? Consider DaVallia Art & Accents and Bonnie's Bundles Dolls. Enjoy the area's slopes with skiing, and don't miss out on the sledging and ice skating.
Map
Chester, VT

What's nearby

  • DaVallia Art & Accents - 16 min walk - 1.4 km
  • Bonnie's Bundles Dolls - 3 min drive - 2.1 km
  • Vermont Country Store - 12 min drive - 12.1 km
  • Magic Mountain Ski Resort - 22 min drive - 21.1 km
  • Okemo Mountain Resort - 22 min drive - 21.9 km

Getting around

  • Bellows Falls Station - 21 min drive
  • Springfield, VT (VSF-Hartness State) - 16 min drive

Restaurants

  • ‪McDonald's - ‬12 min drive
  • ‪Springfield Royal Diner - ‬14 min drive
  • ‪Country Girl Diner - ‬18 min walk
  • ‪The Sub-Way - ‬13 min drive
  • ‪Riverside Restaurant - ‬13 min drive

Frequently asked questions

Does Circa 1868 Chester Home-Less than 20 MIN TO OKEMO have a pool?

Yes, this property has an indoor pool.

Is Circa 1868 Chester Home-Less than 20 MIN TO OKEMO pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Circa 1868 Chester Home-Less than 20 MIN TO OKEMO?

Check-in begins at 4:00 PM.

What time is check-out at Circa 1868 Chester Home-Less than 20 MIN TO OKEMO?

Checkout is at 11:00 AM.

Where is Circa 1868 Chester Home-Less than 20 MIN TO OKEMO located?

This family-friendly Chester holiday home is located in Chester Depot, within 2 mi (3 km) of DaVallia Art & Accents and Bonnie's Bundles Dolls. Vermont Country Store and Vermont Museum of Mining and Minerals are also within 9 miles (15 km).

Reviews

10

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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Annette T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Would stay again
The property had plenty of space for our group. The beds and linens were comfortable and had everything we needed. The owners labeled the important items which was helpful, and quick to respond. The ski/mudroom was an added bonus. I would recommend this property.
Stayed 3 nights in Feb 2025

10/10 Excellent

Margaret L.

Liked: Cleanliness, check-in, communication, location
Friends' Family ski trip!
This house was so lovely for a ski weekend with friends and our families. The house is very well stocked with basic needs and coffee. I LOVED that everything was labeled to help us know what to do, what to not touch and how to work things! Such a unique historic house to stay in that we pass all the time when heading to ski! Great location for an easy 20 minute to Okemo and convenient store across the street! Our families really loved being able to spend time together in this house.
Stayed 2 nights in Mar 2025

10/10 Excellent

Curtis H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Magical
We had a wonderful stay and multigenerational Thanksgiving feast there. It was perfect. The house was everything and more. It snowed on Thanksgiving day which added to experience.
Stayed 3 nights in Nov 2024

10/10 Excellent

Sadie N., Parkville, MO

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay
This was a fantastic property and stay for a family getaway. We would choose it again and again!
Stayed 5 nights in Dec 2021

10/10 Excellent

Kathy M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend family ski
Property was beautufil old large home.
Stayed 2 nights in Feb 2024

10/10 Excellent

Christina S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Ski house
This was a perfect location, short ride to Okemo for skiing and close to lots of restaurants. The house was exactly as pictured and had everything we needed for a great stay. Lots of attention to detail by the owners, we loved all the little signs around the house. We had a great experience and would stay here again!
Stayed 3 nights in Jan 2024

10/10 Excellent

Marguerite D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic house!
Gorgeous & centrally located home with plenty of room for both entertaining and privacy. We had a blast and the hosts are so sweet and helpful!
Stayed 2 nights in Jul 2022

10/10 Excellent

Maureen W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property in a great location
We stayed here for our son’s wedding. The space is beautiful. The beds were very comfortable! The home owners thought of everything. There was plenty of coffee, towels, toilet paper, trash bags, etc. So many things you forget in a typical rental! The outside yard was also fun! Thank you for a wonderful stay!
Stayed 4 nights in Sep 2024

10/10 Excellent

Hilary C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely Stay
This house is a combo of homey and historic. The beds are very comfy and bedrooms spacious. There is a piano (and guitar) that the kids loved to play and it is situated very close to the downtown Chester area. Would recommend for your next VT getaway!
Stayed 2 nights in Sep 2021

10/10 Excellent

Ilana V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Can’t beat this!
My family and I stayed in this extremely unique and character-filled house in the heart of Chester. It was very clean and the host took the extra step of providing clear labels of where things are. There was even a piano and guitar. The local market is right across the street on the corner, which we frequented. You really can’t beat this. We ran out of dishwasher detergent and the host responded promptly, having the property manager bring it by within 20 minutes. Will definitely stay again!. Thank you.
Stayed 2 nights in Nov 2024

10/10 Excellent

Leitha B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was perfect!
This is such a lovely, big, old house that is beautifully maintained and very clean! The owners were extremely accommodating and the house had everything we needed for our small family reunion. I highly recommend!
Stayed 3 nights in Jun 2023

10/10 Excellent

Kathy M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Impeccable, Charming Place to Stay
We had a wonderful time staying at this charming farmhouse. It was spacious, immaculate and well stocked with everything we needed to have a wonderful girls weekend. The bedrooms, dining room and living room were comfortable for spending hours gathered around a meal or chatting. The location gave us all kinds of options, from grabbing a pizza around the corner, enjoying downtown Chester, stopping in to the Vermont Country Store or having dinner in Ludlow. Would highly recommend staying here any time of year. We really enjoyed our stay. Particularly because the hosts provided excellent communication from start to finish.
Stayed 2 nights in Jun 2024

10/10 Excellent

David b., New York

Great House and Close to Ski Slopes
We stayed at this house in February. The house was spacious, clean and great for our large extended family. Jen was very responsive to a few small questions/requests we had. Would definitely stay at this house again.
Stayed 5 nights in Feb 2018

10/10 Excellent

Samantha H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming, historical and enchanting home
We had a wonderful time at this lovely Vermont home. It was perfectly situated for day trips around Vermont. And it gave us lots of space to spend time together. Thanks for sharing it with us.
Stayed 5 nights in Aug 2021

10/10 Excellent

Sarah M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A cozy spot with lots to love
We had an incredible time staying here for my friend’s bachelorette party. I was a bit worried about staying during such a hot weekend, but the air conditioners in the bedrooms helped to keep us cool. The hosts were kind enough to leave us a note and a bottle of chilled wine in the fridge, which got our weekend off to a great start! They were communicative, kind, and impeccable hosts. The house is very cute and close to restaurants that took me by surprise with how good they were! Would definitely recommend to anyone for a cozy escape in a beautiful VT home!
Stayed 2 nights in Jul 2024

10/10 Excellent

Charles M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great House!
This house is beautiful. The beads were very comfortable. It had original features with modern touches. It was great for my family getaway to Magic Mountain. Thank you. We will be back next year!
Stayed 3 nights in Mar 2023

10/10 Excellent

Donna K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quaint home in Chester
Our family so enjoyed our weekend in Chester. Our family lived in Chester for 20 years and we wanted to have a family visit. This charming Victorian was a perfect house (lovingly restored) for our family . Jennifer was a great host and communicated throughout our stay and was able to allow us to check in sooner as a snow storm came through earlier than expected . We will definitely come back!
Stayed 2 nights in Dec 2021

10/10 Excellent

Nick M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful home in a classic small-town setting.
We had a great stay at this lovely, historic home with classic architectural features yet filled with modern comforts. Loved the wood floors and high ceilings and original moldings and fixtures. Visited the local town of Chester - don't miss the Southern Pie Cafe. Spent a great afternoon at Artisan Park in Windsor - the Path of Life Sculpture Garden was a surprising bonus. Thanks for a wonderful experience.
Stayed 3 nights in Aug 2019

10/10 Excellent

Dave O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome Stay
Stayed for the weekend to attend wedding in town. Wonderful place that had everything we needed. Had a little trouble locating the key, was attached to railing on the steps leading to the door. Called the hosts number and was immediately answered and advised where the key was located. Allowed us to check in early to get ready for the wedding. Great communication and would definitely stay again. Short trip to Okemo for those who ski and Chester is quaint little New England town. Excellent location IMO.
Stayed 2 nights in Mar 2024

10/10 Excellent

Melissa S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Vermont Weekend Getaway
We really enjoyed this property. The house was spacious, exactly as described. So many nice little touches throughout. What a comfortable and clean home. The little market across the street was perfect for what you need for a weekend without needing to head to a large grocery store. I would 100% recommend a stay here to anyone looking. Oh! And this fantastic pizza spot with live music 2 minutes away…Pizza Stone. Fantastic venue for all ages.
Stayed 3 nights in Sep 2023

10/10 Excellent

Sandra S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Authentic New England
We had a lovely stay in this very clean, nicely decorated home. I grew up in New England and can attest that this is a well restored Victorian. Many original floors, huge windows, moldings, bathrooms that function well but have an authentic feel. There is a great little market within walking distance and we enjoyed several local restaurants. This was my first house rental and I was nervous, but it all went smoothly and the communication was great with the owners.
Stayed 4 nights in Jul 2022

10/10 Excellent

Brian S.

Large Comfortable Accomodations
My family and I all met up in Vermont for a ski weekend at Okemo and this house gave us exactly what we needed. There is plenty of space to relax after long days on the mountain and a decent kitchen to cook meals in. The kitchen has the basics but if you need anything special bring it yourself. The house is clean and well cared for with nice little details of Vermont throughout. One nice surprise was the mattresses; they were the most comfortable we'd ever slept on in a rented house. We would definitely stay here again.
Stayed 2 nights in Mar 2018

10/10 Excellent

Deb T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Large house with plenty of room for friends and family
The queen beds were super comfy. The rooms were light and airy. Be aware that there are no shades on the windows so car headlights and morning sun could be an issue. We had a group over for dinner, and there was room at the dining room table for 10. The kitchen is well supplied. The house is right across the street from Smitty's Market which is fully stocked with deli and specialty items. The wood floors are beautiful so you are asked to remove your shoes at the door. The appliances are all pretty new.
Stayed 3 nights in Oct 2021

10/10 Excellent

Verified traveller

Lovely old house
We rented the house (3 couples and a teenager), because we were attending a family wedding nearby. The house is really stunning: carefully preserved and tastefully decorated, with huge windows and high ceilings. The beds are comfortable, and there are little space heaters in the bedrooms. The owners responded quickly to my questions, and were unperturbed when we wanted to increase the body count from 5 to 7. Parking is tight, but there seems to be ample space on the street, on weekends. There's a well-stocked market across the street, and a charming pub with good food (MacLaomainn's) within walking distance. We would rent this house again in a heartbeat. Highly recommended!
Stayed 2 nights in Oct 2018

8/10 Good

Sandy F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
3-generation family bacation
We enjoyed exploring the area; the house was very spacious and nicely decorated—the beds are so comfortable! Based on the pictures, we were expecting to be able to walk down to the river at the end of the lawn, but that is not possible, it is a steep drop-off. The grocery store is literally across the street—so handy! It is on a busy road with trucks going by. We were unable to open the windows in some of the rooms. The circuits in the kitchen were tripped 3 times during our stay—perhaps the electrical system needs to be upgraded. The owners were very responsive to our questions.
Stayed 6 nights in Aug 2022

About the host

Hosted by Jennifer & Michael

Host profile image
Hello! Welcome!

We are Jennifer (a Connecticut native) and Michael (a lifelong Floridian). We share a vision to create a cozy and relaxed atmosphere so you can reset, explore and enjoy your stay!

About us:

Jennifer is an avid runner and a self proclaimed foodie (let me know if you need a restaurant recommendation!), minimalist and hygge enthusiast!

Michael loves playing music-(specifically strumming the guitar) and tinkering on projects in the workshop.

We love the sun and the snow, traveling to new places and adventuring with our 17 year old daughter, Emma and 8 year old son, Reed.

Why they chose this property

We were instantly drawn to this home the moment we first stepped inside! It exudes charm and character at every turn.

Languages:

English

Premier Host

They consistently provide great experiences for their guests