Updating...

Enter dates for more accurate prices

Chester Rentals

Filter

Bedrooms

  • Any
  • 1+ Bedrooms
  • 2+ Bedrooms
  • 3+ Bedrooms
  • 4+ Bedrooms
  • 5+ Bedrooms
  • 6+ Bedrooms
  • 7+ Bedrooms
  • 8+ Bedrooms
  • 9+ Bedrooms
  • 10+ Bedrooms
  • 11+ Bedrooms
  • 12+ Bedrooms
  • 13+ Bedrooms
  • 14+ Bedrooms
  • 15+ Bedrooms

Price range

Per night

$10 - $500

Chester Rentals

10 flats

Vermont Farmhouse Rooms to share

Chester room

1 bedroom / 2 bathrooms / Sleeps 2

$60

1 / 10

Hugging Bear Inn - Tower Room

Chester b and b

1 bedroom / 1 bathroom / Sleeps 2

$119

1 / 10

Amare Guesthouse, renovated in-town victorian

Chester house

3 bedrooms / 2 bathrooms / Sleeps 6

$230

1 / 22

Hugging Bear Inn - Bear Cub Room

Chester b and b

1 bedroom / 1 bathroom / Sleeps 4

$139

1 / 10

Classic Vermont Farmhouse

Chester Depot farmhouse

5 bedrooms / 2 bathrooms / Sleeps 14

$310

1 / 12

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

Chester house

5 bedrooms / 2 bathrooms / Sleeps 10

$135

1 / 24

Historic 1868 Carriage House at Chester Depot

Chester guest house

3 bedrooms / 1 bathroom / Sleeps 6

$150

1 / 19

Hugging Bear Inn & Shoppe- rent entire Inn

Chester b and b

6 bedrooms / 7 bathrooms / Sleeps 18

$590

1 / 30

Hugging Bear Inn - Bear's Den Room

Chester b and b

1 bedroom / 1 bathroom / Sleeps 5

$139

1 / 11

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

Chester house

3 bedrooms / 2 bathrooms / Sleeps 8

$175

1 / 10
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more