Four Chimneys Inn – Beautiful B&B in Vermont

View from the back of the Four Chimneys
Beautiful gardens..
Living my best life truly ;)

Last week Emma and I had the incredible opportunity to stay at the beautiful Four Chimneys Inn while visiting Vermont. It was the perfect place to act as a home base for all the leaf-peeping and driving around that we had planned and we were so excited. We couldn’t wait to finally visit the popular New England towns in person and see fall in Full colorful grandeur! This has been a trip that we’ve looked forward to for as long as we can remember and we were thrilled. (The Four Chimneys Inn was recently named Vermont’s best Bed & Breakfast in 2019 by Yankee Magazine. Not surprised after staying there!)

The Old First Church in Bennington, Vt.
The gardens at Four Chimneys Inn.

History of Bennington

Four Chimneys Inn is located in Old Bennington, an adorable spot with tons of history. The town sits near the state lines of New York and Massachusetts and it was the first town chartered in the state of Vermont – way back in 1749 by the New Hampshire Governor. The town’s original settlement was formed in Old Bennington, in 1761. These early settlers were resistant to land claims from the New York colony… As a matter of fact, there was an organized citizen militia headed by no other than Ethan Allen himself known as the Green Mountain Boys. This militia later played a crucial role at the Battle of Bennington on August 16, 1777. That battle was a prelude to the surrender of British General John Burgoyne at Saratoga, which led directly to the success of the Revolution. So interesting! This is a place Jeff needs to visit. He loves history..
(Thanks to the Bennington website & Museum for the history lesson)

Entry of the Inn – Lynn is the cutest.
Hanging in the entry of the Inn –
Norman Rockwell painted this scene of a boy and his dog waiting for Santa at the Four Chimneys Inn.

History of the Four Chimneys Inn

Dating back to the late-1700s:
In 1783, the original building of the Four Chimneys Inn was the home of the town’s pastor, Reverend David Avery. Unable to afford the upkeep he sold it to Nathanial Brush, a notable participant in the battle of Bennington. Brush turned the mansion into a boarding house & general store but in 1910 the mansion burnt to the ground, leaving only the foundation. Philip B. Jennings, a prominent local businessman, saw promise and rebuilt the estate in 1913 and kept it as a summer home for he, his wife and daughter. They lived there on and off until his death in 1949. With over 12,000 square feet the Inn is huge! I can’t imagine it acting as a home for just 3 people. In the 1950’s the mansion was sold and turned into a fine dining establishment. Famous clientele included Elizabeth Taylor, Richard Burton, and Walt Disney! The mansion was also used as a backdrop for many weddings because of the beautiful expansive grounds. In 2005 innkeepers Lynn and Pete purchased the Four Chimneys Inn and turned the mansion into a beautiful bed & breakfast.. They pride themselves on keeping the historic elements of the mansion intact.

The sitting room opposite the front door

The Inn Itself

From the minute we arrived at the Inn we fell in love with it’s cozy and intimate vibe. The living room had a fire lit and there were guests enjoying their nightly cocktails.. The staff is warm & welcoming as is the Inn itself and we were made to feel right at home.

Main living room

Our room was located on the 2nd floor and it was gorgeous. It’s painted a soft light blue color and filled with mahogany furniture. With hardwood floors and a fireplace our room felt so luxurious. An added bonus – all rooms have super comfy memory foam mattresses. So spoiling when traveling away from home. The bathroom was large with a huge jet tub, shower and all the amenities that one can think of. The innkeeper, Lynn designed each room herself using a mix of colors and styles. Love that! Luckily for us, we were able to take a sneak peek into a couple of the other rooms and take a few pics to share with you. I love how different each of the spaces look & feel!

Room 1. Our room. :) So beautiful
We loved having a fireplace in our bedroom. It warmed us perfectly during the chilly nights.
First floor room with a 3rd bed and handicap facilities
Room #2, Love that wallpaper!
The cottage.
The cottage bedroom. This cottage is the perfect solution for families since it has a 2nd story with additional beds.
The covered porch that sits next to the dining room.
View from the dining room to the garden
Emma and I loved our homemade breakfast.
Our yummy beautiful breakfast

One of our favorite parts of the Inn is the gorgeous breakfast served each morning. Every night before heading to bed you are given a menu for the next day’s breakfast selections and a choice on times to eat.. This prep works cuts the waiting time for breakfast in half in the morning.. perfect for someone like me who isn’t a morning person. ;)
The dining room has a fine-dining look & feel and everything is thought of. There is a coffee/juice bar for self service and breakfast is served immediately. Lynn arrives early every morning to whip up the breakfasts herself and I can’t emphasize enough what an amazing cook she is. Everything was so yummy! I can’t wait to share the orange-infused blueberry cream cheese french toast recipe with Jeff. My favorite!
The only issue I had about our visit is that I wasn’t able to sample every breakfast. We’ll have to stay longer next time. ;)

My favorite – the hydrangea trees in the garden.
Gorgeous flowers everywhere
The porch decorated with baby pumpkins.

The grounds and gardens surrounding the Inn are just as gorgeous as the Inn itself. Beautifully maintained, they’re made for a wedding or party on the lawn. Four Chimneys has the cutest porch overlooking the grounds as well.. it’s the perfect spot to sit in, relax and enjoy an afternoon tea or cocktail.

If you’re thinking of visiting the Four Chimneys Inn, especially for Fall Foliage, make sure to book out a few months in advance. There are only 11 rooms (+ the cottages) so the B&B fills up quickly. Click here to see the different room comparisons/booking availability.

Hildene, The Lincoln Family Home.
Lincoln’s Bust in his Son’s Library.

Nearby Activities

There are so many fun things to do near the town of Bennington. Famous towns such as Woodstock and Manchester are also a close drive away.

A few local favorite activities:

The Old First Church of Bennington.
Robert Frost’s grave at the Old First Church.
  • Old First Church – Make sure to visit Old First Church. This church is a short 5 minutes walking distance from the Four Chimneys Inn. It’s both beautiful and historic.. the first church built in Vermont in the early 1800’s. If you’re a fan of poets, the cemetery is also historic. Robert Frosts’ gravesite is located here.
  • Bennington Potters – 1 mile away from the Inn. Visit the largest working craft pottery in the U.S.
  • Bennington Museum – Walking distance from the Inn. Bennington is rich in history and there is so much to learn about the area here.
View from Lincoln’s home – Hildene. Ombre and beautiful.
View from the back of Hildene.
What a view from this home.
Hildene is a gorgeous property.
Hildene beauty
Hidden dining room
The dining room decorated for fall.
The living room.
Lincoln’s Library.
  • Hildene, the Lincoln Family Home – Lynn recommended that we visit Hildene and we’re so happy that she did! Abraham Lincoln’s oldest son, Robert Todd Lincoln built the estate as his summer home in 1905. It’s stunning and full of history with many famous people visiting over the years. Today you can see the estate with over 90% of the original furnishings and they’ve made sure to keep the interiors designed the way the family had them. The gardens are formal and the surrounding mountains are the perfect backdrop for photos.
  • Robert Frost Stone House Museum – around 7 miles from the Inn. Literary landmark, Frost resided in the home from 1920-1929 during which he composed the extremely famous poem, “Stopping by Woods on a Snowy Evening.”

We had such an amazing time in Vermont with our stay at the Four Chimneys Inn a definite highlight! Next year we’ll have to bring Jeff and Emma’s boyfriend with us.. Jeff lives for historic sites and I just know he would love to see the Inn in person. If you’re traveling through Vermont I suggest staying at least one night at Four Chimneys Inn if possible… you won’t regret it! From the thoughtfulness of the Innkeepers to the beautiful home and grounds themselves it’s become one of our new favorite places to visit.
Click here to book a stay & to learn more.


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15 thoughts on “Four Chimneys Inn – Beautiful B&B in Vermont

  1. Wow what a WONDERFUL getawAy! I’ve been thinking about planning a solo trip for my 40th biRthday (still a few years away yet!!!!) and thanks to your post And stories about this trip i may have found it!!! What a beautiful inn! I visited Old Bennington years ago and fell in love but that was in the summer…. Now i may need to become a ‘leaf peeper’ and re-visiT in the fall! Thank you for your INSPIRATION kristy!!!
    Kind regards amanda x

  2. Kristy,
    I love it, i love it all. This trip is what i have been dreaming of my whole adult life. I can’t wait to visit VT. now I have Clarity on where to visit and The BB, Amazing! Disney dined there! wow. Thank you so much for this amazing blog, i’m going to save it for future REFERENCE. Well done.

    1. You’ll love it Marcela. Emma and I had so much fun. The Inn is gorgeous and everyone bent over backwards to make sure we had a great stay. :) Hugs!

  3. What a beautiful bed and breakfast. I feel like your visit was just like being in a real lofe hallmark movie! A QUINTESSENTIAL town and views to dIe for. What a FABULOUS fall getaway.


    1. Aww.. Thanks so much Lynn! We loved meeting you as well and will cherish our time visiting! You have built such a cozy beautiful home for everyone to visit.. I can’t wait to bring Jeff the next time. :) Hugs!! xx

  5. What an ABSOLUTELY charming Inn in one of thr most Charming, and historic, Parts oF OUr country. Love the Ethan Allen connection! I enjOyed following your trip and seeing The gorgeous fall colors! xo