Hugging Bear Inn & Shoppe- rent entire Inn

From $550 / night

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  • 6 bedrooms
  • 7 bathrooms
  • Sleeps 18
  • B&B

This listing is an option for renting the entire Inn. Individual rooms can be rented as well. Please check our other listings for individual rooms. Thank you!!!

Bed & Breakfast Inn and Teddy Bear and Toy Shop.

The Inn - an historic Victorian residence circa 1850, is an enchanting B & B in the Vermont tradition.It is located in the center of Chester, VT, on the green, a very beautiful quintessential Vermont town setting. Stay in one of six guest rooms blending 19th century charm and modern touches, each with a private bath and air conditioning. Rooms accommodate couples, singles, families and children. And you will find a Teddy Bear in every bed! ...Read more


Hugging Bear Inn & Shoppe- rent entire Inn
Chester, Vermont

What's Nearby:

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Additional Location Information

We are located on the Main street in the center of Chester, Vermont, on the green. Chester is a very beautiful quintessential Vermont town setting with shops, bookstore, galleries, restaurants across the street on the green and within walking distance. Close by: skiing, golfing, swimming, hiking, biking, wildlife, museums, theater, music and more.

About Chester - The Misty Valley

Chester is a small Vermont village nestled in the Eastern slopes of the Green Mountains in the Williams River Valley, along the South Central tier of the state. Our citizenry is not as diverse as some places but we do have a fine mix of natives and those from away - some from far, far away who have happily decided to make Chester their home too.
Our population is small compared to our landmass -- around 3,000 residents within 56 square miles, which can make for a solitude not found in a city. And our land offers some of the most diverse and beautiful landscapes imaginable. You'll never grow tired of experiencing our hills and mountains, valleys and streams, rocky ledges and pastures. In all seasons, Chester is a wonder to behold.
The three branches of the Williams River come together in downtown Chester as they head through Rockingham to the Connecticut River. The North Branch begins in Andover, runs through Ludlow then turns south along Route 103 through the Stone Village. The South Branch runs from Tater Hill Golf Course along Popple Dungeon Road before turning north at the Grafton Road. And the Middle Branch runs from Andover to Chester along Route 11.
There are numerous spots for fishing or dipping along each branch.
Because of the way that Chester sits along these branches and the various mountains that divide it, our weather patterns between areas can be almost as diverse as our landscape. Popple Dungeon may be getting hit with a snowstorm while Main Street is sunny -- or vise versa. What definitely happens in this area is morning mists rolling off the mountains.
Two Historic Districts
The town is comprised of two districts in the National Register of Historic Places: The Stone Village Historic District (also known as the Stone Houses at Chester Depot) are on both sides of Route 103 North. It consists of 10 Greek Revival buildings that also includes a former school (now a home) and a Unitarian Universalist Church. This district was recognized in 1974.
The Chester Village Historic District, also known as South Village, was recognized in 1985. It is roughly bounded by Lovers Lane Brook, Maple Street, the Middle Branch of the Williams River and Lovers Lane. Its historic significance is its mix of Late Victorian, Colonial Revival and Federal style architecture. These homes, houses of worship and businesses were built between 1750 and 1924.
Currently, there are 40 Historic Districts in Vermont.
Here are a few numbers you should know:

Chester has 1. Zero stoplights 2. One ZIP code -- 05143 3.Two gas stations 4. One phone exchange -- 875 (Vermont only has one Area Code -- 802).

More About This Location

Mountain nearby, Rural retreats, Warm winter getaways

Getting There

Nearest train station: Bellows Falls, 12 miles
Car is recommended


Last updated on February 12, 2015
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  • Linens Provided
  • Corporate bookings allowed
  • Long term rentals allowed (over 1 month)
  • Central heating
  • High chair
  • Soap/Shampoo Provided
  • Alarm Clock
  • Hair dryer
  • Iron
  • Towels Provided
  • A/C or climate control
  • Bachelor or bachelorette parties allowed
  • Ceiling Fans
  • Local Guides/Maps
Phone / Internet
  • Internet Access
  • Telephone
  • Fax Machine
Property Features
  • Parking
  • Secure parking space
  • Refrigerator
  • Freezer
  • Microwave
  • Television
  • VCR
  • Satellite or cable TV
  • Books
  • DVD Player
  • Balcony or terrace
  • Porch
  • 12 Dining chairs
  • Pet friendly - no
  • Smoking allowed - no
  • Suitable for children - yes
  • Suitable for the elderly - ask
  • Wheelchair accessible - no

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