Bed and Breakfast in Chester, VT
6 guests · 3 bedrooms · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this bed and breakfast
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.
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.
Amenities at 1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!
Non-smoking
No pets allowed
Map of Chester, VT
Ratings and reviews
Summary of reviewsGuests enjoyed the comfortable amenities, convenient location, and charming atmosphere of the property. Owners were helpful and responsive. Would highly recommend for a relaxing getaway.
8.0 / 10.0Excellent·Dec 2025
Check in was very easy, in fact we got an email saying we could check in early.
10.0 / 10.0Outstanding·Jun 2025
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!
8.0 / 10.0Excellent·Jun 2025
We enjoyed our stay at the Carriage House; it was clean and comfortable, and had everything we needed. Definitely would return!
6.0 / 10.0Average·Jul 2025
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.
$$$$
Top rated by guests
9.4Outstanding
(43 Ratings)
Guests enjoyed the comfortable amenities, convenient location, and charming atmosphere of the property. Owners were helpful and responsive. Would highly recommend for a relaxing getaway.
From real guest reviews summarized by AIDon't miss out! Price and availability may change
