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Chester Rentals

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Price range

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$10 - $500

Chester Rentals

About Chester

8 flats

Hugging Bear Inn - Tower Room

Chester b and b

1 bedroom / 1 bathroom / Sleeps 2

$119

1 / 10

Hugging Bear Inn - Bear Cub Room

Chester b and b

1 bedroom / 1 bathroom / Sleeps 4

$139

1 / 10

Hugging Bear Inn & Shoppe- rent entire Inn

Chester b and b

6 bedrooms / 7 bathrooms / Sleeps 18

$590

1 / 30

Amare Guesthouse, renovated in-town victorian

Chester house

3 bedrooms / 2 bathrooms / Sleeps 6

$230

1 / 22

Hugging Bear Inn - Bear's Den Room

Chester b and b

1 bedroom / 1 bathroom / Sleeps 5

$139

1 / 11

NEW! 5BR Chester Home - On Tree Farm Near Skiing!

Chester house

5 bedrooms / 2 bathrooms / Sleeps 10

Responds fast! avg. 16 minutes

$135

1 / 24

Historic 1868 Carriage House at Chester Depot

Chester guest house

3 bedrooms / 1 bathroom / Sleeps 6

$150

1 / 19

The 1843 Stone House - Chester, VT (3bdrm/ 2 ba)

Chester house

3 bedrooms / 2 bathrooms / Sleeps 8

$175

1 / 10

About Chester

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For scenic beauty in the middle of a vibrant and historic area, consider Chester for your next vacation destination! Most of the shops and restaurants throughout Chester can be found along Main Street, but the town is small enough that anything you wish to reach can be accessed by foot.

While you're in Chester, be sure to also make time for these destinations that highlight the rich history and beautiful scenery of the area:

  • Chester Historical Society: Learn more about the town's proud history with the exhibits and artifacts found at this long-standing museum.
  • Chester Vietnam Conflict Monument: Located in the middle of downtown, this monument is dedicated to the men and women in Chester who served in the Vietnam War.
  • Play Golf: Tater Hill Golf Club is a nine-hole course that provides an afternoon of fun for all ages and skill levels.
  • Go Skiing: Nearby Okemo Mountain is considered one of the premier destinations for skiing in the entire country.

There are great events in Chester throughout the year, ranging from live performance to parties that stretch across town. Watch chainsaw carvers show off their skills at the Big Buzz Chainsaw Carving Festival in October, sample the works of over 60 local craftsmen and artisans at Chester's Fall Craft Fair in September, or watch dozens of hot air balloons soar through the sky at the Quechee Vermont Balloon Festival in May.

Whether you're looking for a picturesque condo or apartment just steps from the outdoor recreational options throughout town, or a cozy cabin with mountain views, there's a vacation rental that will put you exactly where you want to be in Chester.

If you're looking to explore the rest of Vermont, Chester is a great location to use as a base for a series of day trips. The big city of Burlington and the outdoor attractions of Stowe can both be reached within an hour by car.

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