The Hugging Bear Inn & Toy Shoppe


244 Main St

Chester, VT

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Country Inns and Teddy Bears are both symbols of warmth, closeness and family ties. They belong together! Teddies of every size and personality give the Inn a homey touch all its own. The Teddies have plenty of company in the shop. You’re likely to find anything from aardvarks to zebras and a lot in between.

We have the largest selection of Steiff collectibles, One-of-a-kind artist’s bears and Muffy Vanderbear in the Northeast. You will find puppets (Folkmanis and others), Webkinz, Gund, Boyd’s, Bearington, Princess, Douglas, jewelry, cards, cups, shirts, hats, books and endless other bearaphernalia.

In 1850, a unique Italian Colonnade home was built and situated across form the village green in Chester, Vermont. It saw many years, many seasons and went through many changes. It had different owners, was a schoolhouse for a period and went through the Victorian era, which changed this home into a beautiful Queen Anne style Victorian home by adding a tower, bow windows and a big wrap around porch. Circa 1905, a Carriage House was constructed on the property. One of the finest examples of carriage barns in New England, it shares the Colonial Revival style – notably the gambrel form of roof – with several contemporary Chester village buildings. The projecting loft gable and the pyramidal-capped cupola distinguish the finely executed barn.

In 1982, this Victorian home went through another transformation when it was renovated to accommodate guests with a private bathroom in every bedroom. The Hugging Bear Inn was born and continued to welcome families, children, and everyone from all over the world that love Vermont, enjoy a Bed and Breakfast Inn and, most of all, have a passion for Teddy Bears. Teddy Bears, you ask? Yes, the theme of the Hugging Bear Inn revolves around teddy bears, family, fun, collecting and enjoying the lovely countryside of Vermont.

Not long after the Inn was established, the Hugging Bear Shoppe began. It’s a gift shop that quickly grew from one to four extensive rooms of the finest selection of teddy bears in the Northeast, with over 10,000 teddy bears and similar products available for purchase.


The Hugging Bear Inn & Shoppe, which began in 1982, resides in an elegant 150-year-old Victorian residence.  Chester VT incorporated in 1764 and is now home to two National Historic Districts; the Stone Village and the Village Green, of which the Inn is a significant part.  Also nearby is the old town cemetery that dates back to the Revolutionary War.


Stay in one of the six guest rooms blending 19th century charm and modern touches, each with a private bath.  Rooms accommodate couples, singles, families and children.  And you will find a Teddy Bear in every bed!  Included in your room rate is a hearty country breakfast, including Pure Vermont Maple Syrup.  Seconds? Certainly!


The Hugging Bear Inn & Shoppe offers a wide variety of gathering places for guests, including a comfortable living room, cozy den and spacious front porch with a swing. Enjoy conversation, television, internet, board games, toys, a good book, or just sit back and relax.



The Hugging Bear Inn is a magical and enchanting bed & breakfast inn in the old Vermont tradition. We welcome children of all ages to our lovely Victorian Inn filled with fun and Teddy Bears.


The Hugging Bear Inn & Toy Shoppe
244 Main St
Chester, VT

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