The Four Chimneys Inn

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Luxury
4.0 star property
9.4

Exceptional

Upscale bed & breakfast near Old First Congregational Church

Located close to Bennington Museum and Bennington Battle Monument, The Four Chimneys Inn provides free full breakfast, an adjacent golf course, and a terrace. Treat yourself to a massage or other spa services. In addition to a garden and a fireplace in the lobby, guests can connect to free in-room WiFi.

Popular amenities

  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
  • Bar

Room options

Available filters for rooms
Showing 11 of 11 rooms

View all photos for Deluxe King Room, Sitting Area, Private Bathroom, Jetted Tub, RM-1

A bedroom with a four-poster bed, a ceiling fan, a fireplace, and a view of the outdoors through large windows.

Deluxe King Room, Sitting Area, Private Bathroom, Jetted Tub, RM-1

  • 25 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Signature King Room, Sitting Area, Private Bathroom, RM-2

A bedroom with a four-poster bed, a sofa, a chair, a small table with cups and a teapot, and a window with curtains.

Signature King Room, Sitting Area, Private Bathroom, RM-2

10.0 out of 10
Exceptional
(1 review)
  • 29 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Deluxe King Room, Sitting Area, Private Bathroom, RM-3

A bedroom with a four-poster bed, a sitting area with a sofa, and a fireplace.

Deluxe King Room, Sitting Area, Private Bathroom, RM-3

10.0 out of 10
Exceptional
(1 review)
  • 24 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Traditional Queen Room, Private Bathroom, RM-4

A bedroom with a four-poster bed, a vanity with a mirror, and a green armchair.

Traditional Queen Room, Private Bathroom, RM-4

10.0 out of 10
Exceptional
(3 reviews)
  • 19 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Signature Room, King plus Twin Bed, Private Bathroom, 3rd floor-stairs, RM-5

A bedroom with a large bed, two bedside tables, a chair, a radiator, and a ceiling fan.

Signature Room, King plus Twin Bed, Private Bathroom, 3rd floor-stairs, RM-5

10.0 out of 10
Exceptional
(3 reviews)
  • 33 sq m
  • Sleeps 3
  • 1 King Bed and 1 Twin Bed

View all photos for Traditional Queen Room, Private Bathroom, 3rd floor-stairs, RM-6

A bedroom with a large bed, two chairs, a small table, and a nightstand.

Traditional Queen Room, Private Bathroom, 3rd floor-stairs, RM-6

10.0 out of 10
Exceptional
(1 review)
  • 17 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Traditional Queen Room, Sitting Area, Private Bathroom, 3rd floor-stairs, RM-7

A bedroom with a large bed, two bedside tables with lamps, a window with curtains, and a framed floral artwork on the wall.

Traditional Queen Room, Sitting Area, Private Bathroom, 3rd floor-stairs, RM-7

  • 21 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Deluxe Cottage, King Bedroom plus Loft, Sitting Area, Private Bathroom, RM-8

A cozy attic bedroom with a bed, a small sofa, a nightstand, and a window with blinds.

Deluxe Cottage, King Bedroom plus Loft, Sitting Area, Private Bathroom, RM-8

10.0 out of 10
Exceptional
(1 review)
  • 23 sq m
  • Sleeps 3
  • 1 King Bed and 2 Twin Beds

View all photos for Signature Cottage, King Bedroom, Sitting Area, Private Bathroom, RM-9

A bedroom with a bed, a green sofa, a small table, and two windows with curtains.

Signature Cottage, King Bedroom, Sitting Area, Private Bathroom, RM-9

10.0 out of 10
Exceptional
(3 reviews)
  • 24 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10

A bedroom with two beds, a nightstand, a lamp, and a window with curtains.

Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10

  • 28 sq m
  • Sleeps 3
  • 1 King Bed and 1 Twin Bed

View all photos for Deluxe King Room with Sitting Area, Private Bathroom, Porch, RM-11

A spacious bedroom with a large bed, two armchairs, and a sofa. There is a fireplace, a window with curtains, and a view of the outdoors.

Deluxe King Room with Sitting Area, Private Bathroom, Porch, RM-11

  • 25 sq m
  • Sleeps 2
  • 1 King Bed

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About the neighborhood

Located in Bennington, The Four Chimneys Inn is in the historical district and next to a golf course. Don't miss out on a visit to Bennington Center for the Arts. Enjoy the area's slopes with cross-country skiing and downhill skiing, and don't miss out on the snowshoeing. Visit our Bennington travel guide
View more B&B in Bennington
Map
21 West Road, Bennington, VT, 05201

What's nearby

  • The Washington Monument in Washington, D.C.
    Bennington Battle Monument
    14 min walk - 1.3 km
  • Old First Congregational Church
    7 min walk - 0.6 km
  • Bennington Museum
    13 min walk - 1.1 km
  • Bennington Center for the Arts
    16 min walk - 1.4 km
  • Southern Vermont College
    19 min walk - 1.7 km

Getting around

  • Albany Intl. Airport (ALB)
    52 min drive

Restaurants

  • Cumberland Farms
    4 min drive
  • McDonald's
    4 min drive
  • Burger King
    5 min drive
  • Starbucks
    5 min drive
  • Starbucks
    4 min drive

About this property

The Four Chimneys Inn

  • Upscale bed & breakfast near Old First Congregational Church
  • Located close to Bennington Museum and Bennington Battle Monument, The Four Chimneys Inn provides free full breakfast, an adjacent golf course, and a terrace. Treat yourself to a massage or other spa services. In addition to a garden and a fireplace in the lobby, guests can connect to free in-room WiFi.
  • Other perks at this bed & breakfast include:
    • Free self parking
    • Express check-out, luggage storage, and wedding services
    • Coffee/tea in the lobby, concierge services, and meeting rooms
    • Guest reviews speak highly of the helpful staff
  • Room features
  • All guestrooms are individually furnished, and include comforts such as premium bedding and air conditioning, as well as thoughtful touches like free WiFi and bathrobes.
  • Other conveniences in all rooms include:
    • Bathrooms with shower/tub combinations and free toiletries
    • Flat-screen TVs with cable channels
    • Wardrobes/closets, heating, and daily housekeeping

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Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi and wired internet

Parking and transportation

  • Free self parking on site
  • Wheelchair-accessible parking available

Food and drink

  • Free full breakfast available 7:30 AM to 9:00 AM on weekdays and 8:00 AM to 9:30 AM on weekends
  • A bar/lounge
  • Coffee and tea in common areas

Things to do

  • 18-hole adjacent golf course

Conveniences

  • Limited-hour front desk
  • Luggage storage

Guest services

  • Concierge services
  • Housekeeping (daily)
  • Wedding services

Business services

  • Meeting rooms

Outdoors

  • Garden
  • Picnic area
  • Terrace

Spa

  • Massage

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Assistive listening devices
  • No elevator
  • Wheelchair-accessible parking
  • Wheelchair-accessible path of travel

More

  • 3 buildings
  • 3 floors
  • Built in 1913
  • Fireplace in lobby
  • Georgian architecture
  • Smoking not allowed

Room amenities

Bedroom

  • Hypo-allergenic bedding
  • Premium bedding

Bathroom

  • Bathrobes
  • Free toiletries
  • Hair dryer
  • Private bathroom
  • Shower/bathtub combination
  • Towels provided

Entertainment

  • Flat-screen TV with cable channels

More

  • Air conditioning (climate-controlled)
  • Heating (climate-controlled)
  • Individual decor
  • Individual furnishings
  • Iron/ironing board

Policies

Check-in

Check-in start time: 3 PM; Check-in end time: 9:00 PM

Minimum check-in age: 25

Check-out

Check-out before 11 AM

Contactless check-out available

Express check-out available

Special check-in instructions

The front desk is open daily from 7:30 AM - 9:30 PM

Guests must contact the property in advance for check-in instructions; front desk staffed during limited hours

To make arrangements for check-in please contact the property ahead of time using the information on the booking confirmation

If you are planning to arrive after 8:30 PM please contact the property in advance using the information on the booking confirmation

Information provided by the property may be translated using automated translation tools

Access methods

Front desk (limited hours)

Pets

Pets not allowed

Children and extra beds

Children 5 and younger are not allowed at this property; All guests older than 5 are welcome

Rollaway/extra beds are not available

Cribs (infant beds) are not available

Property payment types

American ExpressDiscoverMastercardVisa

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 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
This property accepts credit cards; cash is not accepted
Cashless transactions are available
Safety features at this property include a carbon monoxide detector, a fire extinguisher, and a smoke detector

We should mention

This property does not have elevators
This property's policy is to refuse certain bookings for the purpose of group events or parties, including pre-wedding stag/bachelor and hen/bachelorette parties
Children 5 years old and younger are not permitted at this property

Frequently asked questions

Is The Four Chimneys Inn pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Self parking is free at this property.

What time is check-in at The Four Chimneys Inn?

Check-in start time: 3 PM; Check-in end time: 9:00 PM.

What time is check-out at The Four Chimneys Inn?

Check-out is at 11 AM.

Where is The Four Chimneys Inn located?

Situated in Bennington, this golf bed & breakfast is within a 10-minute walk of Old First Congregational Church and Bennington Museum. Bennington Center for the Arts and Bennington Battle Monument are also within 15 minutes.

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

The Four Chimneys Inn Reviews

9.4

Exceptional

9.6

Cleanliness

9.4

Location

9.6

Staff & service

9.4

Property conditions & facilities
Rating 10 - Excellent. 229 out of 291 reviews
Rating 8 - Good. 41 out of 291 reviews
Rating 6 - Okay. 15 out of 291 reviews
Rating 4 - Poor. 6 out of 291 reviews
Rating 2 - Terrible. 0 out of 291 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Peaceful and whimsical stay in a historic inn. The breakfast was delicious (served with the best local maple syrup) and location was a 5 minute drive to the downtown area.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Had a great experience here. The staff was friendly and helpful. Chatting with the bartender and other guests at the bar over a nightcap made for an enjoyable evening. The room was clean and comfortable and the breakfast was fantastic.
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A very tasteful inn: excellent decor / extremely comfortable!
Stayed 2 nights in Sep 2023
Verified review

6/10 Okay

Liked: Cleanliness
The property was in a great location.
Stayed 4 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful Inn with downtown not far away for shopping, antiques. Fabulous restaurant on the premises. GREAT coffee!
Stayed 2 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
Wonderful, cozy inn with a fabulous restaurant. No wonder it was listed as one of the 11 best places to stay in Vermont by Travel and Leisure Magazine. Simply excellent!
Stayed 1 night in Mar 2024
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Made a quick overnight to Bennington on our runaround of Vt and loved this property. Walkable to historic sites and downtown. Friendly owners and staff and excellent breakfast. If you’re considering Bennington I would highly recommend the 4 Chimneys Inn
Stayed 1 night in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The check-in with Kim (?) was easy and pleasant and she was very helpful with Monday night restaurant recommendations. The room was cool and very comfortable. A lovely place to stay!
Stayed 1 night in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Cozy and Comforting.

The property and the innkeepers were lovely. Nice location to walk to local historic homes and sites. Their menu and service were excellent. The rooms were clean, cozy and you could tell care and love went into the property.
Stayed 1 night in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Home away from home!

What a charming B&B . So warming and inviting.Staff made you feel at home and were all so kind and friendly.Oh and the food was delicious,
Stayed 1 night in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful inn and restaurant. Owners and staff are extremely hospitable. They provide thoughtful amenities and create a warm, peaceful atmosphere for guests. We enjoyed meeting others at dinner and the piano bar/lounge; everyone shared our enthusiasm.
Stayed 2 nights in Nov 2023
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This is a beautiful quiet classic Vermont Inn. The food was great and the room was beautiful. Located in a lovely small Southern Vermont town. We enjoyed hiking nearby. Highly recommend.
Stayed 2 nights in Nov 2023
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place is beautiful! We received a friendly greeting, and were given all the information that we needed for a great stay. Our room is spacious and comfy.
Stayed 1 night in Apr 2024
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We loved our stay at the Four Chimney Inn. Great Inn in Bennington. We stayed in the small house in the back which was great for 4 people. The breakfast was delicious and the staff was great. The only strange thing is that the lounge is also the bar and it closes at 9:30pm which means there is no common area where you can sit and just relax.
Stayed 2 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Old world comfort in a quaint VT village

Comfort and luxury in every detail. My first stay. Thoroughly impressed with the personnel, the room and the food. Will definitely return!
Stayed 1 night in Jan 2024
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
Out of the way from main part of town. Beautiful area, quiet, safe,peaceful. Friendly owner. Convenient checkin.
Stayed 1 night in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Beautiful, cozy Vermont inn

We had an excellent stay at the Four Chimneys Inn. We've been staying at different places in the Bennington area each time we're there. This was our first at this inn, but it is definitely one of our top picks. Friendly staff, very cozy room (and inn overall), good location, excellent breakfast. Our only disappointment was that they weren't serving dinner on the two nights of our stay. We'll have to come back to try out the restaurant next time. Overall, we highly recommend it.
Stayed 2 nights in Feb 2024
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The owners are there everyday. The staff is friendly and very custimer focused. The standards are high and the inn has a great history and is lovely. It felt more like being a house guest than a customer. The restaurant was an outstanding choice for dinner and accommodation for vegetarians and allergies were taken into consideration and excellent meals with tasty desserts and great wine and cocktails now has this on our summer spots to visit!!
Stayed 2 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff / owners were friendly. If you stay here make sure you don't skip a meal. I had the scallops for dinner. I I live on Cape Cod where scallops are a staple. The presentation and the tastes rival the best the Cape has to offer at double the price. Exquisite. Breakfast was excellent too. I normally don't give 5 stars anywhere. This spot exceeded expectations.
Stayed 1 night in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We quite liked this hotel as it was charming and well thought out in many ways. We especially loved the dinner we had the first night. Our room had a fireplace and we loved that feature because it was a bit chillier than we expected. The only thing we would have wished for was a mini fridge in the room, but that’s not a huge deal breaker for us to return someday. It Is a nice walkable area and an easy to navigate town. Sadly, Bennington Pottery store isn’t open to the public anymore, but the town and surrounding area afforded us many diversions to fill up 3 days.
Stayed 3 nights in Apr 2024
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Super cute carriage house with everything we needed. The service was amazing I called a few hours ahead since I was running a bit early after driving 6 hours and they let me check in a bit early. Unfortunately we didn’t get to experience breakfast as we were at a family function until late which was after the time the menu was due but I’m sure it would have been as amazing as everything else on the property!
Stayed 1 night in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Quaint and beautiful property. The staff and services were very good but not seen much. Our first breakfast wasn’t as expected the potatoes were overcooked and the apple juice canned. The remaining breakfast’ were very good and perfect portions. Sorry we couldn’t have dinner there as planned but we‘ll just have to return next year!! 🤗😃
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This is a beautiful, historic property and pretty consistent with the photos on the website. The room I had was just as pretty with some antique furnishings, but of course in person you notice that it is an old building. The room was a great size, and I loved the hardwood floors. The bathroom was also large and you are provided a sundry of items for convenience. The bed was comfortable, though it did seem to have a center depression. The only other issue I had was that though the the showerhead seemed to have a dial to adjust pressure, I was not able to. Overall the property is in great condition. The staff were welcoming, and the breakfast was outstanding, served in their traditional, historic, and charming restaurant space.
Stayed 1 night in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Lovely place very comfortable
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay!
Stayed 2 nights in Sep 2024