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All hotels in Chester, Vermont, United States of America
1 room, 2 adults

Hugging Bear Inn and Shoppe, Chester

2.5-star2.5 stars
244 Main StreetChesterVT05143United States of America

No-frills B&B in Chester
  • Free cooked-to-order breakfast and free WiFi in lobby
  • Collect nightsYou can collect® Rewards nights here


Delicious food
Great location
Tasty breakfast
More comfort would be nice
29See all 29 reviews
From 64 reviewsTripAdvisor Traveller Rating

Hugging Bear Inn and Shoppe, Chester

from $119
  • The Tower Room
  • The Bear Den
  • Sunshine Room
  • Teddy Roosevelt Room
  • The Tree House Room
  • Bear Cub Room

What’s around Hugging Bear Inn and Shoppe, Chester


  • Grafton Historical Society - 7.5 mi / 12.1 km
  • Vermont Museum of Mining and Minerals - 7.6 mi / 12.2 km
  • Grafton Valley Arts Guild Cricketers Gallery - 7.6 mi / 12.2 km
  • Hunter Gallery of Fine Art - 7.6 mi / 12.2 km
  • Gallery North Star - 7.7 mi / 12.4 km
  • The Nature Museum - 7.7 mi / 12.5 km
  • Grafton Ponds Outdoor Center - 8.3 mi / 13.4 km
  • Okemo Mountain Resort - 13.5 mi / 21.7 km

Getting around

  • Springfield, VT (VSF-Hartness State) - 15 min drive
  • Rutland, VT (RUT-Rutland Southern Vermont Regional) - 43 min drive
  • Lebanon, NH (LEB-Lebanon Municipal) - 48 min drive
  • Bellows Falls Station - 19 min drive
  • Claremont Station - 33 min drive
  • Windsor Station - 38 min drive
  • Limited parking

At a glance

Key facts

Hotel size

  • 6 rooms


  • Check-in time starts at 2 PM
  • Check-out time is 11 AM
The front desk is open daily from 8 AM - 8 PM

Required at check in

  • Credit card or cash deposit required

  • Government-issued photo ID required

  • Minimum check-in age is 18

Travelling with others


  • No cribs (infant beds)


  • Pets not allowed


  • Free WiFi in public areas

At the property

Food and drink
  • Free cooked-to-order breakfast daily
  • Front desk (limited hours)

In the room

Freshen up
  • Private bathroom
  • Shower only
  • Daily housekeeping

Recent reviews

Fabulous 8.6 From 29 reviews

Hugging Bear Inn and Shoppe, Chester
Go some place else
The inn keeper (not owner) Kristen was absolutely fabulous. The Inn itself definitely needed so TLC. Little to no window curtains, especially when there are other hotels right across the street. Not even headboards on the beds. I understand that some Inns dont do TVs, but they really should. Only tv was in the living room. Absolutely under no circumstances take room 6. It is a forgotten room that you need to go outside across a balcony to get to. Very uncomfortable.
Lori, us3 night trip
Hugging Bear Inn and Shoppe, Chester
Very Good8.0
The place overall was great and close to food/shopping/etc. The service was amazing and polite. We booked a room for 3 . Pics were deceiving. 1 ended up on an old worn out hide a bed that was crammed tight once open. Very uncomfortable but the environment outside of sleeping was pleasant
corey, us1 night trip
Hugging Bear Inn and Shoppe, Chester
wonderful stay
great in a pleasant historic location. nicely located a short drive to the Weston play house. friendly inn keeper.
Chris, us1 night trip
Hugging Bear Inn and Shoppe, Chester
Excellent B&B
Excellent B&B, relaxing and service was great. Nice homemade breakfast cooked to order was very good! Would stay there again.
John, us2 night romance trip
Hugging Bear Inn and Shoppe, Chester
Quaint Vermont B&B type inn
Quaint - quiet Vermont B&B - clean room - great staff - near Okemo ski resort
Kevin, us1 night romance trip

See all reviews

Hugging Bear Inn and Shoppe, Chester

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