Chester Depot Vacation Rentals, Houses & More


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1 / 12

Classic Vermont Farmhouse

  • 5
  • 14
  • 2 nights min

$308

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Great rentals within 20 miles that match your search

1 / 10

Hugging Bear Inn - Bear Cub Room

  • 1
  • 4
  • 1 night min

Inquire for Rates

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1 / 8

Lakefront vacation home - sleeps 10

  • 4
  • 10
  • 3 nights min

$249

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1 / 12

3 bedroom lake home on Crescent lake

  • 3
  • 7
  • 2 nights min

$214

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1 / 17

**Spectacular Green Mtn Natl Forest Retreat **

  • 5
  • 10
  • 7 nights min

$497

Details

1 / 26

25 Acre Mtn Playground, 2 Bd, Great Ski Access, Close to Okemo, VAST trails

  • 2
  • 6
  • Min stay varies

$125

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1 / 16

Okemo Slopeside Rental located at the Main Base!

  • 1
  • 2
  • 2 nights min

$373

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1 / 32

Cozy room with homemade breakfast

  • 1
  • 2
  • 1 night min

$75

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1 / 9

Vermont Country Lake House

  • 5
  • 14
  • Min stay varies

$149

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1 / 16

Fox Run -- Sleeps 10 - 12, Only 1 mile from Okemo Jackson Gore Base

  • 4
  • 12
  • 2 nights min

$397

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1 / 20

Little Brook House at Echo Lake

  • 5
  • 13
  • Min stay varies

$219

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1 / 28

6 BR Lake House in VT Green Mountains

  • 6
  • 14
  • Min stay varies

$291

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1 / 26

Charming Ski Chalet Close to Main St & Okemo Mtn

  • 3
  • 13
  • 2 nights min

$273

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1 / 21

3 Season Cabin - sleeping porch lake trails playground

  • 3
  • 9
  • 2 nights min

$85

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1 / 10

Stratton 4 Bedroom Home

  • 4
  • 11
  • Min stay varies

$249

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1 / 10

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

  • 3
  • 8
  • Min stay varies

$174

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1 / 29

Ski Bromley & Stratton, sleep 8 at Bromley Village

  • 3
  • 8
  • Min stay varies

$249

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1 / 27

Ludlow Cabin Near Okemo Ski Lodge

  • 3
  • 6
  • 2 nights min

$249

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1 / 24

Live & Breathe VT- Village Home, Yoga Studio, Ski!

  • 4
  • 9
  • 3 nights min

$249

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1 / 17

Cozy 4BR Ski Chalet-1mile to Okemo base + hot tub

  • 4
  • 12
  • Min stay varies

$249

Details

1 / 15

3 BDR Farmhouse on Tranquil 105 acre Organic Farm

  • 3
  • 8
  • 3 nights min

$262

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1 / 5

Foster Farmhouse East Wing - Alyson's Orchard

  • 3
  • 8
  • 2 nights min

$596

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1 / 20

Large, Lovely, Affordable Mountain Home

  • 5
  • 10
  • 30 nights min

$83

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1 / 16

Classic Village Farmhouse with large yard & stream

  • 4
  • 9
  • 7 nights min

$185

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1 / 20

Lake Warren-Alstead-Walpole-Keene- Fall Foliage Rates

  • 4
  • 4
  • 3 nights min

$134

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1 / 16

Mountain Side Condo

  • 6
  • 1 night min

$224

Details

1 / 22

Reilly's Rest in the Green Mountains, Kid and Pet friendly!!

  • 3
  • 8
  • 2 nights min

$148

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1 / 12

Charming and cozy Log cabin near Stratton Vermont

  • 4
  • 6
  • 2 nights min

$298

Details

1 / 24

9 BR Lakefront Luxury Getaway on 10 Acres with a Lake

  • 9
  • 20
  • Min stay varies

$745

Details

1 / 25

Remodeled carriage house 1/2 mile from Okemo, walk to Ludlow Village!

  • 1
  • 4
  • 2 nights min

$84

Details

1 / 27

Charming waterfront cottage on Echo Lake - 2 dogs welcome!

  • 3
  • 7
  • Min stay varies

$154

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1 / 39

Spacious home, great for large groups! Hot tub, game room, 2 miles to Okemo.

  • 3
  • 10
  • Min stay varies

$99

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1 / 55

Lovely cottage by Lake Pauline w/60-ft water frontage access, private dock!

  • 2
  • 6
  • Min stay varies

$114

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1 / 24

Condo near Okemo Mountain w/ shared pool - long-term renting available

  • 1
  • 4
  • Min stay varies

$82

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1 / 33

Ski-in/out condo at Okemo w/ a fireplace and beautiful views!

  • 3
  • 10
  • Min stay varies

$139

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1 / 26

Classic lakefront A-frame on Lake Pauline. Okemo Mtn Resort only 2 miles away!

  • 2
  • 8
  • Min stay varies

$121

Details

1 / 27

Ski-in/ski-out home w/seasonal shared pool. Ideal for your next Vermont trip!

  • 1
  • 6
  • 2 nights min

$249

Details

1 / 26

Condo with a shared seasonal pool & tennis courts - walk to ski trails!

  • 1
  • 6
  • Min stay varies

$84

Details

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