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1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!

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Exterior detail
Dining
Interior
Interior
Interior detail

Reviews

9.4 out of 10
Exceptional

Popular amenities

  • Free WiFi
  • Parking available
  • Laundry
  • Kitchen
$199
avg per night

Explore the area

View in a map
Chester, VT
  • Place, DaVallia Art & Accents
    ‪16 min walk‬
  • Place, Bonnie's Bundles Dolls
    ‪3 min drive‬
  • Place, Okemo Mountain Resort
    ‪19 min drive‬
  • Airport, Springfield, VT (VSF-Hartness State)
    ‪14 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Guest Room 1

1 Queen Bed

Guest Room 2

1 Queen Bed

Guest Room 3

1 Queen Bed

1 bathroom

Bathroom

Bathtub or shower · Toilet

Spaces

Kitchen
Separate dining area
Garden
Dining area
Price is $199 avg per night

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About the neighborhood

Chester

Chester Depot, a neighborhood in Chester, is home to this guesthouse. Baltimore Covered Bridge and Phineas Gage Memorial are local landmarks, and some of the area's activities can be experienced at Okemo Mountain Resort and Crown Point Golf Course. Traveling with kids? Consider DaVallia Art & Accents and Bonnie's Bundles Dolls. Be sure to check out the area's animals with activities such as game walks and birdwatching.
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What's nearby

  • DaVallia Art & Accents - 16 min walk - 1.4 km
  • Bonnie's Bundles Dolls - 3 min drive - 2.9 km
  • Okemo Mountain Resort - 19 min drive - 24.3 km
  • Killington Resort - 41 min drive - 56.3 km
  • Stratton Mountain Resort - 43 min drive - 50.4 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬13 min drive
  • ‪Country Girl Diner - ‬18 min walk
  • ‪Md's Cybah Bier Garten - ‬16 min drive
  • ‪Dunkin' - ‬14 min drive
  • ‪The Copper Fox - ‬13 min drive

About this property

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!

Our Carriage House is less than a mile to charming Chester Village-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!

Our quaint and cozy Carriage House, which once held horses in the 1880's is located in Okemo Valley and is perfect for city dwellers looking for a country escape, traveling families, romantic getaways, retreat weekends, girls trips, holiday stays, reunions, celebrations etc;

Our beautifully appointed space will make for a relaxing and peaceful getaway.

*Please note the main living areas (dining, kitchen, bedrooms, bathroom) are located on the second floor of the converted barn. There is a flight of stairs from entryway to living areas*

The Carriage House offers 3 bedrooms each with queen memory foam mattresses. It comes equipped with full kitchen amenities for preparing fresh meals from the local farmer's market or country store across the street. We provide fresh ground coffee, creamer and assorted teas. There's even a laundry room! We are also happy to provide a Pack and Play, high chair and baby gates for those traveling with little ones.

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 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, snowshoes 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.

DISTANCE FROM CARRIAGE 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, gym-we do not have these items, nor have them selected as an option**

We don't live on the property, but we have a caretaker nearby who can assist if needed. If an issue arises, please contact us right away so that we can solve it and you can relax + enjoy your stay!

We're only a text or phone call away!

You will find that cell phone service is sporadic in this southern region of Vermont-the Carriage House has a landline phone and long-distance service. (US & Canada)

In Summer months-we have a window unit AC-we do not have central air.
Our prices include all fees. No hidden fees.

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 0-17
Pack and Play, baby gate and highchair available
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Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted
Outside only

Check-out instructions

The host requires you complete the following before checking out:
Remove leftover food and drinks and take out the trash
Turn off the lights, lock the doors, and return the keys
Failure to complete these may result in a negative review from the host.
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
Cashless transactions are available
Onsite parties or group events are strictly prohibited
Long-term renters welcome
This property uses eco-friendly cleaning products
Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock

Frequently asked questions

Is 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!?

As of Apr 3, 2026, prices found for a 1-night stay for 2 adults at 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! on Mar 16, 2026 start from $199, 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?

Onsite parking is available at the property.

What time is check-in at 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!?

Check-in begins at 4:00 PM.

What time is check-out at 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!?

Check-out is at 11:00 AM.

Where is 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! located?

This family-friendly Chester guesthouse 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 mi (15 km).

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! Reviews

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 33 out of 43 reviews
Rating 8 - Good. 8 out of 43 reviews
Rating 6 - Okay. 1 out of 43 reviews
Rating 4 - Poor. 0 out of 43 reviews
Rating 2 - Terrible. 1 out of 43 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Greg H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great spot, and great communication. Super easy to stay there
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

brian b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice 3 bedroom carriage house. Everything you need for an easy stay. Comfortable beds, washer dryer, stayed warm on a very cold weekend.
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Zsolt M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time. Charming place. Lots of room. Very close to the mountain.
Stayed 4 nights in Dec 2025
Verified

8/10 Good

Judy T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Check in was very easy, in fact we got an email saying we could check in early.
Stayed 2 nights in Dec 2025
Verified

8/10 Good

Julie S.

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

Nice stay at the Carriage House

We enjoyed our stay at the Carriage House; it was clean and comfortable, and had everything we needed. Definitely would return!
Stayed 5 nights in Jun 2025
Verified

10/10 Excellent

Jason Y.

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

Wonderful place to stay in Chester!

We had a great time on our family ski trip.
Stayed 4 nights in Jan 2023
Verified

10/10 Excellent

Narda C.

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

Delightful Carriage House

This space was more than expected. The beds were super comfy and everything we needed was at our fingertips whether it be coffee making supplies, dish soap or Kleenex. Hosts use environmentally friendly products that are also allergen friendly. they provided lots of local information which helped us plan our stay. Loved this spot!
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

elena v.

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

Great location!

In the heart of town, this is a great location! Quaint historic carriage house is perfect for a weekend get away!
Stayed 2 nights in Jan 2023
Verified

10/10 Excellent

Chris A.

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

Great place!

Convenient location, clean, had everything we needed. Close to Okemo. Anything you need is a close drive away!
Stayed 3 nights in Mar 2024
Verified

10/10 Excellent

Doug M.

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

Just perfect

Very tasteful and comfortable Wonderful area and gracious host
Stayed 4 nights in Oct 2019
Verified

10/10 Excellent

Rebecca M.

Great little property

Thank you for helping us have a great ski vacation! The carriage house is warm, clean and the beds are comfortable. Would book again!
Stayed 4 nights in Mar 2018
Verified

10/10 Excellent

Marty M.

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

Great Stay!

We enjoyed the unique flavor of the house. There was a nice backyard with a fire pit. Kids ages 21, 18, and 12 all loved the house as well as the community. Would definitely stay again.
Stayed 2 nights in Jul 2022
Verified

10/10 Excellent

Jane B.

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

Very Comfortable

Adorable and comfortable Carriage house. Very comfortable beds! Chester is a cute town and close to several ski mountains.
Stayed 2 nights in Mar 2023
Archival

10/10 Excellent

Flip L.

One of the coolest gems - A perfect vacation home

We loved out stay there. We live in a big city and came here for a vacation to get away from it all. It's such a neat town with so much character. WiFi works great and there is a convenient little store that you could throw a rock to, it's so close. We would stay there again in a heartbeat. Thanks for the hospitality.
Stayed 2 nights in Aug 2017
Verified

10/10 Excellent

Pamela R.

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

Totally awesome!

Clean. Easy. Perfect. Quaint. Exactly what we were looking for
Stayed 3 nights in Aug 2023
Verified

10/10 Excellent

Martha C.

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

Exceptional and convenient

Jenn’s carriage house was one of the best places we have ever rented. The house is well equipped and SUPER clean. The beds were very comfortable and the space is very quiet. There were guests in the front house during our stay but we never heard noise. Jenn provided some of the basics in the kitchen and laundry room. We look forward to renting the space again.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Lydia C.

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

Big Comfortable Space Good Location

We stayed here for 4 nights and we're very comfortable. The kitchen is set up for use, and it is less than 500 feet to a typical Vermont country store for provisions. Very clean and everything worked well. There are stairs to get to the rooms so if stairs are hard, look closely at the picture. A great big living room and dining table. Be aware that there is only one bathroom, it wasn't a problem for us, but with the max number of people it might be. Nice place, good location, good manager.
Stayed 4 nights in Jun 2024
Verified

10/10 Excellent

Lynne D.

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

Cozy and Comfortable

We stayed for 20 days in January to enjoy skiing at Okemo, which was a short trip from the Carriage House. It was better than described on the listing with more amenities than expected. The kitchen was stocked with everything needed for cooking and baking-except for the groceries. The modern appliances and crockpot allowed me to cook with ease. Having a washer/dryer on site, as well as detergent, was very convenient. Hosts Jennifer and Michael provide a detailed description of how everything works in the house and various things to do in the area. Pre-stay communication was very helpful in planning our stay and knowing what to pack. Definitely will stay here again!
Stayed 20 nights in Jan 2025
Verified

8/10 Good

Robert B.

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

living room furniture

most unconfortable couch and chairs would not rent again because of this
Stayed 2 nights in Aug 2019
Verified

8/10 Good

Rachel W.

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

Nice place. Close to skiing

Nice place for our weekend ski trip to Okemo. Kids enjoyed having their own rooms. The kitchen was well-stocked (thanks for the coffee and cream!) and the bathroom soaps were a welcome surprise. The house is connected to the main house and shares a wall, but no access. If arriving at night, the yellow house is the right place. Just head towards the back of the house, and you’ll be all set! Overall, the place was great. We would be delighted to stay again!
Stayed 2 nights in Jan 2023
Verified

6/10 Okay

Pat M.

Liked: Check-in, communication
Disliked: Cleanliness
More "rustic" than expected or desired. There was a long crack on the dining area wall and the wood flooring was very rough and in need or resurfacing. The only air conditioning was a small window model on the upper level which only cooled the bedroom up there and the laundry area. Though we stayed in late July, all the decor was wintry. A sled and ski poles and snow shovels, with winter scenes on the walls. Including a hand written welcome sign in the laundry room all about winter life. There were old pieces of latice nailed over the living room windows so that no one would try to open them. The stairs down to the lower yard were in rough conidition and looked as though they would break under foot. We didn't try them because of this. The kitchen facilities were very nice and we appreciated that. This is not somewhere we will return to.
Stayed 3 nights in Jul 2025
Verified

8/10 Good

wendy l.

Liked: Cleanliness, check-in, communication, location

Overall good

Overall good. Very clean, well stocked. Pros: * Bed in master bedroom was comfy * Kitchen was spacious and well stocked (thank you for the coffee and tea options!) * Living room/dining room was spacious and comfortable. Enjoyed the pamphlets left in the box in the dining room with ideas of things to do locally. * Wifi worked well * Loved the Mrs. Meyer's cleaning products (hand soap, dish soap) CONS: * The listing description does not mention that this is a second floor unit - glad my parents ended up not coming because they would not have been able to get into the unit. * Description says there is a window AC - this is very literal. There is "A" window AC which is in the laundry room and does not provide air conditioning to any of the 3 bedrooms, nor the kitchen, living room or dining room. We visited during an unusually hot spell, and only 2 windows in the unit open (two bedrooms) - so the 2 extra provided fans only blew around hot air. I did contact the owner who promptly dropped off two more area fans (now using four). To be fair, short of installing more AC units, I'm not sure what the owners could do because they have all of the windows sealed otherwise. * Beds in other 2 rooms were uncomfortable and very noisy when rolling over for 2 teenagers (this is their report so take it for what it's worth). Overall, I think this would be a great place if you're ok with a second floor unit, and it's a more reasonable temperature outside.
Stayed 3 nights in Jul 2024
Verified

10/10 Excellent

Robert M.

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

Relaxing stay

Very clean, spacious and quiet, Perhaps above all, well located: Smitty's well-stocked grocery is across the road, the historic Stone House district is a minute north, Chester Commons a minute south and Springfield and Bellows Falls 20-30 minutes away.
Stayed 3 nights in Aug 2022
Verified

10/10 Excellent

Samantha H.

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

Very nice

Nice place, plenty of space, clean.
Stayed 2 nights in Aug 2022
Verified

10/10 Excellent

Lisabeth G.

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

Great location , Super cute.

The carriage house was in a great location and is super cute. Was nice and cozy, easy to relax in . Located next to the local police station made the girls trip feel safer. I would definitely re-book.
Stayed 3 nights in May 2022

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