We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Hugging Bear Inn & Shoppe

244 Main Street, Chester, VT 05143
Hotel amenities
Book on
TripAdvisor
in partnership with
Trusted partner. We work with Tingo to make your booking as easy as possible.
1 room 1 adult
Enter dates for best prices
Check In Check Out
Check Availability
Book on
or compare prices from up to 200 sites including:
Professional photos
Hugging Bear Inn & Shoppe
View Map
Add Photo Write a Review

40 Reviews from our TripAdvisor Community

Traveler rating
Traveler type
Time of year
Language
East Lyme, Connecticut
Level Contributor
4 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed 2 weeks ago

My friend and I spent the weekend at the Hugging Bear Inn in Chester, VT and it was lovely. We spent Friday and Saturday nights. The house is large and homey and while it's not fancy, it's authentic and inviting. Our room was small and cozy. The toilet/shower were in a tiny space and the sink was in the room... More 

Helpful?
Thank debbrunetti
Mittagong
Level Contributor
7 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
4 of 5 stars Reviewed November 6, 2015

A great charming place to stay. Lovely people who run this place, Bed and Breakfast comfortable and friendly. Breakfast is absolutely fantastic. The rooms are generally large. Our room was a tad smaller than the others, and WiFi a bit unreliable upstairs, but this was not a problem or even a nuisance. Our room was clean and with daily cleaning,... More 

Helpful?
1 Thank Mark S
Milford, Connecticut
2 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
4 of 5 stars Reviewed October 12, 2015

My wife and I stayed over for two nights over the Columbus Day weekend in room # 3 and it was clean and spacious enough for the two of us. The only minor negative to the room was the small bathroom but we were able to make it work. The staff (Candy & Laura) went out of their way to... More 

Helpful?
Thank ebkozie
New England
Level Contributor
38 reviews
36 hotel reviews
common_n_hotel_reviews_1bd8 86 helpful votes
3 of 5 stars Reviewed August 10, 2015

The location is ideal in a picturesque town with a few restaurants in walking distance. For some reason, rooms at peak season (ski weekends, summer weekends, fall foliage) are extremely expensive in this part of Vermont with many local inns charging more than $250/night. For sure, the Hugging Bear represents a lower cost, with room rates about $100/night less than... More 

Helpful?
1 Thank DBS0210
Burlington, Vermont, United States
Level Contributor
13 reviews
9 hotel reviews
common_n_hotel_reviews_1bd8 3 helpful votes
2 of 5 stars Reviewed August 9, 2015 via mobile

My wife and I stayed at the Hugging Bear while on a bike trip of Vermont. We frequently stay at bed & breakfasts around New England and are used to a wide variety and standard of accommodations. Unfortunately, we were very disappointed with our recent stay at the Hugging Bear. While I'm sure that this was once a grand old... More 

Helpful?
Thank SpecnerN
Laura T, Manager at Hugging Bear Inn & Shoppe, responded to this review

I was able to connect and talk with the people who wrote this review. They were grateful for my response and i was grateful to get a chance to hear some candid and constructive criticism. As a result I was able to find a weak link in our staff and system of operation and were able to correct those things.... More 

Clinton, Mississippi
Level Contributor
61 reviews
13 hotel reviews
common_n_hotel_reviews_1bd8 30 helpful votes
5 of 5 stars Reviewed July 28, 2015

This inn is exactly what I hoped it would be. The owner and staff are extremely helpful and accommodating, the breakfast was wonderful, and the town itself is charming. Lots of good restaurants and cute shops right across the street. Loved it and would go again. The shop is also a lot of fun and has a little bit of... More 

Helpful?
Thank Paula R
East Northport, New York
Level Contributor
10 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 8 helpful votes
4 of 5 stars Reviewed February 3, 2015

We enjoyed a snowy weekend with great hosts and a FANTASTIC gluten free breakfast. Hosts Laura and Paul were incredibly friendly and helpful in every way. The CEO is darling!! Vermont is the place to go if you want scenery, hospitality, great food and outdoor activities

Helpful?
Thank Tema L
Ocean City, New Jersey
2 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed January 26, 2015

We were greeted by our very friendly host, Laura, who showed us to our cute room. We loved the charm and character of the hugging bear and the personal touches that were evident throughout the inn. We walked across the street for a delicious dinner at free range. We loved the town of chester. The next morning we had a... More 

Helpful?
1 Thank Katie R
Level Contributor
7 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
3 of 5 stars Reviewed January 19, 2015 via mobile

We stayed at this inn for two nights. The room was clean and spacious and the teddy bear shop was charming. The bathroom and sink were tiny and we were only given two sets of towels though we made an extra payment for our two children. Breakfast was basic - two simple cereals, granola, and instant oatmeal packets plus coffee,... More 

Helpful?
Thank Sunanda N
Level Contributor
4 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 3 helpful votes
3 of 5 stars Reviewed December 31, 2014

Terrific breakfast, very friendly, and hardworking employees. The pancakes were very good and we were happy with all the food accommodations. We were so glad to have a place our young son could stay with us. Was disappointed the room was not cleaner. The bathroom had hair on the floor, tooth paste on the sink from previous guests, dirty mirrors,... More 

Helpful?
Thank Monica S
Laura T, Manager at Hugging Bear Inn & Shoppe, responded to this review

Thank you so much for your review. I am so sorry about the disappointing conditions of your room. It was never our intentions to provide such a dirty room. We actually did not know about this until it was too late. We have made big improvements in the cleanliness of our rooms and of our Inn. We are a family... More 

Questions? Get answers from hotel staff and past guests. Ask a question

18 photos of this hotel

Traveler photos: See what travelers like you saw

Viewed
All traveler photos (7)
Viewed
Room/suite (5)
Viewed
Hotel & grounds (1)
Viewed
Other (1)

Management photos: Courtesy of the property manager

Viewed
All management photos (11)
Viewed
Hotel & grounds (2)
Viewed
Room/suite (5)
Viewed
Other (4)
Check In Check Out
Prices are for 1 room, 2 adults
Show Prices
Hotels you might also like...
Also consider these accommodations in or near Chester
6.4 mi away
Grafton Inn
Grafton Inn
#1 of 1 in Grafton
4.5 of 5 stars 261 reviews
8.6 mi away
The Pointe at Castle Hill Resort
0.1 mi away
Inn Victoria
Inn Victoria
#1 of 10 in Chester
5.0 of 5 stars 435 reviews
Show Prices
Show Prices
Show Prices
0.0 mi away
Chester House Inn
Chester House Inn
#3 of 10 in Chester
4.5 of 5 stars 128 reviews
1.2 mi away
Stone Hearth Inn and Tavern
14.8 mi away
Echo Lake Inn
Echo Lake Inn
#3 of 9 in Ludlow
4.5 of 5 stars 99 reviews
Show Prices
Show Prices
Show Prices
Questions? Get answers from hotel staff and past guests. Ask a question

Amenities

Enter dates for best prices
Check In Check Out
Price Your Stay