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

Family-friendly guesthouse in Chester

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Exterior
Interior
Fridge, microwave, oven, stovetop
Property grounds
Smart TV

Reviews

9.4 out of 10
Exceptional

Popular amenities

  • Free Wi-Fi
  • Parking available
  • Laundry room
  • Kitchen

Explore the area

View 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

Room options

About the area

Chester

A family-friendly stay in Chester awaits you at this guesthouse. You'll be within a 20-minute walk of DaVallia Art & Accents and 2 km (1.3 mi) from Bonnie's Bundles Dolls. Highlights at this guest house include a kitchen, a washing machine and free WiFi. .With a stay at this Chester Depot guest house, you'll be 21.8 km (13.6 mi) from Okemo Mountain Resort.
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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 - ‬12 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.

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Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Internet access

Things to do

  • Games

Conveniences

  • Laundry facilities

Outdoors

  • Garden

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 1 step to reach entrance
  • Area rugs in public areas
  • Hardwood flooring in public areas
  • Upper floors accessible by stairs only

More

  • Eco-friendly cleaning products used
  • Note from host: outside only
  • Smoke-free property

Room amenities

Bedroom

  • Bedsheets provided
  • Memory foam mattress

Bathroom

  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Smart TV

Food and drink

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dining table
  • Electric kettle
  • Hob
  • Kitchen
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Separate dining area
  • Spices
  • Toaster

More

  • Bulk dispensers for toiletries
  • Cleaning products are eco-friendly
  • Desk
  • Desk chair
  • Dryer
  • Eco-friendly toiletries
  • Heating
  • Iron/ironing board
  • Living room
  • Phone
  • Recycling
  • Reusable coffee/tea filters

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM
Contactless check-out

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you to complete the following before checking out:
Remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
Failure to complete these may result in a negative review from the host.

Rules

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

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Note from host: Pack and Play, baby gate and highchair available

Events

No events allowed

Smoking

Smoking is not permitted
Outside only

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
On-site 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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. This property uses eco-friendly cleaning products. Long-term renters welcome. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit and a deadbolt lock in all accommodation. Cashless payment methods are available for all transactions.

Property is also known as

1868 Quaint Cozy Carriage House-perfect Vermont Getaway Slopes

Frequently asked questions

Are there any beaches close to 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!?

The closest beach to 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is Stoughton Pond Recreation Area (14.2 km).

Does 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! have a pool?

No, this guesthouse doesn't have a pool.

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

You bet! With amenities such as laundry facilities, highchairs and travel cots, it's no surprise that 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a winner with our family travellers.

Is there a free airport shuttle available at 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!?

No, 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! does not offer an airport shuttle service.

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

Check-in begins at 4:00 PM. Check-out time is 11:00 AM.

Are pets allowed at 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!?

No, pets are not allowed.

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

Reviews

9.4

Exceptional

Rating 10 - Excellent. 30 out of 40 reviews
Rating 8 - Good. 8 out of 40 reviews
Rating 6 - Okay. 1 out of 40 reviews
Rating 4 - Poor. 0 out of 40 reviews
Rating 2 - Terrible. 1 out of 40 reviews

9.8/10

Cleanliness

Reviews

8/10 Good

Judy T.

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

6/10 Okay

Pat M.

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

10/10 Excellent

Narda C.

Liked: Cleanliness

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

8/10 Good

Julie S.

Liked: Cleanliness

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

10/10 Excellent

Lynne D.

Liked: Cleanliness

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

8/10 Good

wendy l.

Liked: Cleanliness

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

10/10 Excellent

Lydia C.

Liked: Cleanliness

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

10/10 Excellent

Chris A.

Liked: Cleanliness

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

10/10 Excellent

Pamela R.

Liked: Cleanliness

Totally awesome!

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

10/10 Excellent

Jane B.

Liked: Cleanliness

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

10/10 Excellent

elena v.

Liked: Cleanliness

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

8/10 Good

Rachel W.

Liked: Cleanliness

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

10/10 Excellent

Jason Y.

Liked: Cleanliness

Wonderful place to stay in Chester!

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

10/10 Excellent

Robert M.

Liked: Cleanliness

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

10/10 Excellent

Samantha H.

Liked: Cleanliness

Very nice

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

10/10 Excellent

Martha C.

Liked: Cleanliness

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

10/10 Excellent

Marty M.

Liked: Cleanliness

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

10/10 Excellent

Lisabeth G.

Liked: Cleanliness

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

10/10 Excellent

Diron B.

Liked: Cleanliness

Great rustic charm

Fantastic owners, excellent communication, conveniently close to Okemo. I would definitely recommend checking out this unique property.
Stayed 2 nights in Mar 2022

10/10 Excellent

Michael H.

Liked: Cleanliness

Great time!

Wonderful charming country property. Loved waking up and making coffee in the cozy kitchen. Close to several ski resorts and other amenities. We would definitely stay again. The hosts were super friendly.
Stayed 3 nights in Feb 2022

10/10 Excellent

Edward J O.

Liked: Cleanliness

Mini ski trip to Killington & Okemo

Worked out great for us. 3 nice bedrooms for 3 guests . Kitchen had everything we needed. Nice main room to relax. Quiet neighborhood. Jennifer was great on updating us ( within 20 minutes) on why power went out ( someone hitting utility pole somewhere , restored within hour ).
Stayed 3 nights in Feb 2022

10/10 Excellent

Pietro B.

Liked: Cleanliness

Perfect!

This property was absolutely perfect for our ski trip to Okemo. It is warm and cozy, and perfectly equipped for cooking and entertainment. After a long day on the mountain, it's immensely appreciated to be able to stop by Shaw's or Smitty's directly on the way back and then relax within 15 minutes, without a long drive back. Our hosts had thought of everything, even leaving a little basket under the sink in the bathroom in case we had forgotten anything. Would absolutely recommend the Carriage House for any skiers or visitors to Chester, Ludlow, and the surroundings.
Stayed 4 nights in Jan 2022

10/10 Excellent

Virginia R.

Liked: Cleanliness

Perfect getaway

Carriage House was perfect. Had everything we needed. Met the owners and they could not have been nicer. Would definitely book again if in the area.
Stayed 3 nights in Oct 2021

10/10 Excellent

Jennifer B.

Liked: Cleanliness

Fantastic Getaway, Responsive Host

Our weekend getaway with exactly what my family needed. From the very beginning when I had some questions about the property before booking, to the day of check out, Jennifer was a fantastic host. Everything was so clean and well-maintained.
Stayed 2 nights in Jul 2021

10/10 Excellent

Elizabeth R.

Liked: Cleanliness

Terrific COVID Holiday Stay

My husband and I and our teenager and college age child stayed there from right after Christmas through New Year’s. It was a lovely base from which to ski, shop, and sight see. Great having a little grocery next store since we cooked. Just as described and the owners are thoughtful and responsible.
Stayed 5 nights in Dec 2020