Discover The Timeless Charm of The Cheshire Inn

By: Amannda G. Maphies

Stepping foot inside The Cheshire Inn, whether it be the first time or the 100th time, feels a bit like stepping back in history. Across the pond. The infamous ‘Mother Ship’ of America’s breakaway history. The Cheshire Inn has been around for over half a century, and prides itself on hosting guests with the same aesthetic and style as our ancestors intimately knew in England, Britian to be exact, where hospitality was arguably born, and still holds a very note-worthy presence in our modern-day United of States.

This quaint and popular boutique hotel was established in the early sixties. However, the restaurant building (where Bosso, an Italian Gastropub currently resides), dates back to the infamous roaring twenties, when it served guests as Medart’s Restaurant, a popular burger joint very well-known in downtown St. Louis.

It is quite obvious that The Cheshire Inn was inspired by British history. The General Manager, Tony Dandino, shared: “The owners wanted to keep the British feel since it has so much history. The original owner loved the Tudor look and desired to create a hotel that resembled buildings from early English architecture.” Lodging Hospitality Management has owned The Cheshire Inn since 2011. The company frequently visits onsite, though it splits time with the other 17 local hotels and restaurants in the St. Louis metropolitan area.

Each room at The Cheshire is named for a British author, playwright, or poet. A few of the rooms are named after the following: Ian Flemming, William Shakespeare, Jane Austen, and Robert Louis Stevenson. I was exceptionally excited to learn that management had upgraded my standard single-sized room to a suite. And not just any suite, that of the greatest, and arguably most tragic, love story ever told: Romeo and Juliet.

When I walked into the massive suite with glorious hints of young love cleaving to the walls, I was enamored with the large walk-in shower, the massive soaking jetted tub, the king-sized bed with its own zip code, that truly inspired a brief hibernation from the world, not to mention the heavy wooden door leading directly onto the veranda where the hotel pool is located. This suite will surely ruin me for all future stays. As Mr. Dandino, General Manager at The Cheshire, provided a welcome tour and introduced me to many of the themed rooms, I was just as astonished upon entering each one.

When you check into your standard room, large suite or themed room, you receive a complimentary bookmark highlighting the author for which each room is named. Each morening, there is a lovely breakfast, complete with tea service and hot coffee in the welcome area, just across from the front lobby. The food is hot and fresh, the customer service is attentive, and the surroundings truly elicit a deep breath of fresh British air in keeping in line with the hospitable nature of this beloved historic hotel.

Two of the most popular rooms requested are the themed rooms, Treasure Island (during those harsh Missouri winter stays) and the James Bond Suite (highly requested during the sultry summer months). I was delighted to take in the atmosphere of both rooms and neither disappointed. The décor and aesthetic are truly in line with each unique theme. The detail is apparent in every square inch of space in this boutique hotel. From the matching shower tiles to the artistic headboards and the comfortable chaise lounges offered in many of the suites, it is a wonder guests ever see fit to leave their charming home away from home. I simply wanted to maneuver from the enchanting sitting area to the large soft bed, to the jetted tub for a quick soak, and then to lounge in the chaise, while watching television with a spot of tea. No imagination is required at The Cheshire, it truly does all the hard work in writing a script for the most incredible wedding, reception, corporate event, rehearsal dinner, family reunion, vacation, or whatever celebratory event calls each guest to enter these hallowed halls.

I was fortunate to attend a 40th Anniversary party in the upper room of the Basso Restaurant, housed in a building just a short walk from the hotel. The bar at Basso boasts a backdrop of wine bottles from floor to ceiling for a very ‘The Shining’-esque sort of mysterious feel. The catered food was simply divine, the service was top-notch, friendly, helpful, and gave a whole new meaning to the word hospitable. I would never hesitate to hold a fancy function at The Cheshire; it surely fits the bill for a variety of guests, no matter the type of celebratory event.

For a wedding venue, Mr. Dandino recommended at least six months in advance to request a reservation. The reserved spaces fill quickly, especially around the Christmas holiday and other noteworthy months known for life-enhancing celebrations. Guests rave about the charm of this old English-inspired hotel, the period-style décor, the delicious daily breakfast, coffee and tea service, and the friendly and welcoming staff.

When staying at The Cheshire Inn, one does not simply imbibe in a fancy room and all-star customer service, there are several other perks to a get-away at this historic locale. The Fox and the Hound Tavern is located within the hotel. It hosts a very pub-like English feel, complete with a cozy wood-burning fireplace, full bar service, and very comfortable seating for a casual night in with family and friends.

Basso, an Italian Gastropub, offers a large, nearly full-rectangular bar with any palate-pleasing spirit you can imagine. Surrounding the bar are intimate booths, and a few high-top tables, for diners to enjoy the Italian food and delectable spirits in a more upscale atmosphere. The Back Room, a private members-only Cigar Club, is quite breathtaking. The bright stained-glass windows cast shadows on the darker wooden furniture and upscale private gentleman’s club, producing a truly mesmerizing environment. Cigars are available for sale, even if guests do not belong to the infamous member’s-only Private Cigar Club.

Completing the array of businesses onsite is a Starbucks in the same building as Basso. This is not your ordinary Starbucks! The hotel management has taken every liberty with keeping the modern-day coffee shop in line with the historic aura which so delightfully defines the Cheshire. There is a large wood-burning fireplace for guests to enjoy a cup of warm coffee on those bitter Missouri afternoons. There are several tables, booths, and long cushioned seating areas for guests to truly settle in and enjoy everything from an afternoon of work to a morning of quaint conversation with friends.

The Cheshire clientele is comprised of repeat guests, as well as first-time visitors, for business or leisure travel. With St. Louis’ popular Washington University nearby, the Cheshire has been host to years of graduation events and parent visits. According to Tony Dandino, The Cheshire Inn General Manager, move-in weekend at Washington University is one of the busiest times of year for The Cheshire Inn, not to mention graduation, parent’s weekend, and those frequent weekend get-aways in which parents desire a check-in to be sure college is treating their children well.

In addition to Wash U, as the locals call it, The Cheshire is within walking distance of nearby Forest Park, which houses popular tourist attractions for visitors and locals alike, such as: The Kemper Mildred Lane Art Museum, Steinberg Ice-Skating Rink, The Saint Louis Science Center, the Missouri Historical Society Library and Research Center, the Missouri History Museum, The Saint Louis Art Museum, and The Muny. The famous Saint Louis Zoo, and the nationally recognized Barnes-Jewish Hospital, are also located in, or very near, the local Forest Park area.

There are several quaint restaurants, pubs, and wine bars, all within the perimeter of St. Louis’ golden apple, known as Forest Park. The lovely lake allows for kayaking, paddle boats, and a gorgeous sunset view with several resident ducks, while enjoying a glass of wine or a nightcap along the boardwalk located at popular restaurant, The Boathouse. St. Louis locals and guests enjoy walking, running, or biking around the gorgeous park, which boasts spellbinding scenery during each distinct Missouri season.

Speaking of seasons, The Cheshire outdid itself for a themed holiday season last Christmas 2023. They plan to decorate again this year, turning the themed suites into Christmas get-aways for guests. The boutique hotel hires a local company that arrives onsite to decorate the hotel in all of its cheerful seasonal splendor. The lobby plays Christmas Carols 24/7, there are lighted trees located in each guest room, Charles Dickens’ readings located in the cozy reading area for all guests to enjoy, and Santa pictures for visitors with children. Many of the reserved spaces and corporate meeting rooms serve to host those looking for a holiday party or informal get-away for work, with family, friends, or a romantic couples retreat.

In addition, the hotel invites a classical guitar society to visit on the second Wednesday of each month. In February, the hotel installs a bookshelf between the public lobby and the Fox and the Hound pub. This is not just any standard bookshelf. Guests must find the secret spot to open the bookshelf/secret passageway, allowing access to the Fox and the Hound, very reminiscent of the haunted old-English castles of days gone by.

The overarching theme of The Cheshire Inn is built on creating a memorable experience for each guest. The staff works diligently to be sure guests leave happy and vow to return for future visits. The Cheshire aims to provide a fun atmosphere, the opposite of stuffy, robotic, or formal, that one might feel in a more traditional higher-end hospitality venue.

If you love quaint hospitality and an environment that truly feels otherworldly, check out The Cheshire Inn. It boasts countless amenities you simply cannot find in a standard hotel. You will thoroughly enjoy your stay, leave feeling refreshed, with many lovely memories to treasure for years to come. You may even feel a bit melancholy upon leaving, as most Cheshire guests, after their first foray into the elegant Victorian history, turn into loyal and frequent future regulars.

The Cheshire Inn Located in Clayton, St. Louis, MO. For more information or to book your stay visit their website here.