Hugging Bear Inn and Shoppe

244 Main St. , Chester, VT 05143 USA (Show map)


Stay in one of 5 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/playroom and spacious front porch with a swing. Browse and shop in the Teddy bear shop with over 10,000 teddy bears and their friends. Enjoy conversation, television, internet, board games, toys, a good book, or just sit back and relax. Check out the village with its quaint shops and elegant buildings. Churches, restaurants, shops, galleries and lodging surround the village green and bring back the nostalgia of a bygone time. Buy a teddy bear, dine by candlelight, and observe historic architecture. Hiking, swimming, and skiing are all near by.



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  • Guest room4.0
  • Service4.5
  • Value4.5
  • Cleanliness5
  • Onsite Dining4.5

Hugging Bear Inn short stay

4.0 on June 03, 2016

We stayed in the Inn for one night. We found the services, room and breakfast to be well worth the cost. Very pretty, unique, and interesting decor. Chester is a lovely town with access to many nearby points of interest and activity

Fall vacation

5 on October 21, 2011

My wife and I stayed at the Hugging Bear Inn yesterday. Georgette has been running this Inn for over thirty years, in fact we stayed here for the first time twenty five years ago. This recent stay was just as perfect as our first time. The rooms are very clean, and Georgette opens her home to her guests and made us feel like it was our own home. Our day started with Georgette cooking us breakfast. Chester is a very quaint and peaceful town and our room looked down on the town green. Guests are welcome to wander through the teddy bear shoppe at night after the shop is closed to shoppers. We recommend this inn to everyone. No visit to Chester,Vt. would be complete without staying at the Hugging Bear Inn.-Warren Harris.

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Rooms & Rates

Tower Room

Cozy and romantic with queen-sized bed, private bath with shower. Air-conditioning for hot weather days. A round (actually hexagonal) room in the tower of this Victorian home overlooks the village green.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $119 - $139

Bear Den

Overlooking the village green, this bright and spacious room accommodates a family or group of people. Has two queen-sized beds, twin sleeper loveseat, wall-to-wall carpeting, infrared fireplace, private bath with shower and air conditioning for hot weather days.

  • Maximum Capacity: 5
  • Bathroom Private Bath
  • Beds 2 Queen

Nightly Rate: $139 - $159

Sunshine Room

This cheerful and cozy hideaway has a king bed, private bath with shower, and air-conditioning for hot weather days.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $119 - $139

Teddy Roosevelt Room

Bed is king-sized. This room boasts a beautiful bay window with twin sleeper sofa that can pull out for extra sleeping space. Lots of natural light. A comfortable room for resting, relaxing and reading a good book. Private bath with shower and air-conditioning for hot weather days.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 King , 1 Twin

Nightly Rate: $139 - $159

Room #5

A room with calming earth tones. One queen and one double bed. Medium sized room, good for a family. Private bath with shower and air-conditioning for hot weather days.

  • Maximum Capacity: 4
  • Bathroom Private Bath
  • Beds 1 Queen , 1 Double

Nightly Rate: $139 - $159

Tree House

This room has a double bed. It has a private bathroom with a marble floor and an old fashioned claw-foot tub with shower. It is like an upper level hide-away with a porch. Very quiet and very private. One must enter the room by going onto an outside porch and then entering it from a door off the porch. The porch is a nice place to sit and relax, look out over the town, historical society and a revolutionary war cemetery. Cheerful and cozy.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Double

Nightly Rate: $119 - $139

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Location Type

Village Green, Countryside, Mountains, Small town, Village


Albany, NY (ALB-Albany County)

Directions to property:

The Inn and Shoppe are easy to find in the center of Chester (Rte. 11) on the Village Green. Chester is just 8 miles SW of Springfield, VT, and 12 miles NW of Bellows Falls, VT, both on U.S. 91. From the WEST and SOUTH: NY State Thruway to Albany (Exit 23), Rte. 787 North, NY 7 East through Troy to Bennington, VT, U.S. 7 North (22 miles), Exit 4 in Manchester, then Rte. 11 East (28 miles) to Chester. The Inn is on the left. From the SOUTH and EAST: U.S. 91 to Vermont Exit 6, Rockingham, then Rte. 103, 10 miles west to Chester. Do NOT turn right when 103 turns in Chester, continue straight on Main Street. The Inn is on the right, across the street from the village green.

Area Attractions

Antique Shopping, Art Galleries, Gourmet/Fine Dining, Historical interests, Live Music, Movie Theater, National/State parks, Nature area, Outlet Stores, Performing Theater, Picnic area, Religious Services, River, Ski area, Winery

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Inn Details

Establishment type

Bed and Breakfast, Country Inn, Historic Inn

On-site amenities

Board games, DVD Player, Fax Machine, Fireplace, Internet Service, Library, Piano, Satellite/Cable TV, TV, Telephone, VCR, Videos

Room amenities

Air conditioning, Alarm clock, Coffee/Tea facilities, Hairdryer, Ironing Board, Wi-Fi, Wired internet

On-site activities

Bicycle rental, Bicycle riding trails, Bicycles, Bird watching, Boating, Canoeing, Cross-country ski trails, Downhill Skiing, Fishing, Golfing, Hiking trails, Horseback riding, Kayaking, Mountain Bike trails, Shopping, Sight-seeing, Ski rentals, Snow shoe rental, Snow shoe trails, Swimming, Swimming pool, Water sports, Whitewater Rafting

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  • Check In:: 2pm
  • Check Out:: 11am
  • Open All Year Round: Yes
  • Smoking Allowed: No smoking allowed outdoors on front covered porch.
  • Drinking Allowed: Yes
  • Alcohol Provided No
  • Suitable For Children: Yes We are a family oriented Inn. All are welcome!
  • Childcare Provided: No
  • Guest Pets Allowed: No
  • Disabled Access No

Terms and Conditions

  • Minimum Stay: 2 nights on holiday and foliage weekends weekends
  • Accepted payments AMEX, VISA, Discover, Mastercard, Personal checks, Travelers checks, Cash
  • Deposit Amount Required: Reservations may be guaranteed with a deposit via credit card or personal check received within seven (7) business days of making the reservation.
  • Cancellations: Cancellations of less than 7 days notice: Deposit equivalent of one (1) night stay will be charged during high season. $25 cancellation fee for medium and low seasons.
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Laura Thomas, Paul & Diane Thomas

Languages spoken

English, Spanish

Resident Pets


About the innkeepers

Laura - Acupuncture, Herbs, & Energy Medicine. Paul - Vermont Stoneworks. Georgette - Teddy bears and collectibles

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  • Time Served: 8-9am
  • Serving Location: Dining Room

Special meal options


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