Chester Rentals

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13 Houses

Walk to ski trials on Okemo! Private Luxury Chalet

Ludlow chalet

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Fireplace

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Price per night from

$1,374

Oma"s Kottage

Ludlow house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 11

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Price per night from

$345

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

Ludlow townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$460

Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo

Proctorsville house

  • 8 bedrooms
  • 4 bathrooms
  • sleeps 16

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Price per night from

$460

Beautiful Okemo chalet with Hot Tub

Ludlow chalet

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 16

Match: Fireplace

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Price per night from

$374

Match: Fireplace

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Price per night from

$1,380

“The Perfect Vermont Getaway” When I visit Vermont in winter, I tend to go with a mixed crowd. Part of our group are avid skiers/snowboarders, the other part (well, me) are not. This house allows you to experience the best of both worlds, with something for everyone. Situated on top of the mountain (within walking distance to the lodge and with a shuttle that can pick you up right outside the front door), it's in the absolute perfect location for those who like to lace up their boots and hit the slopes. For anyone not playing snow bunny for the day, you are smack dab in the middle of Okemo with plenty of cafes, shopping, and scenic walks just down the hillside (or a very short drive away if you wish to explore). The house itself is also a fantastic, light, open space that is comfortable no matter which straw you draw for beds (we got the twins in the upstairs loft and had one of the soundest sleeps I'd had all winter). Plus, who doesn't love a hot tub. You never feel cramped even with a full house. The living room is an amazing space to just sip coffee and read your book in the morning sunshine or in front of the fire. The owners are extremely knowledgeable, responsive, and helpful, and made sure our stay was top-notch. They have everything outlined for you in a book when you arrive and are there for you should you have any questions. I can't wait to go back next winter!

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Price per night from

$1,840

PennRock Lakeside

Ludlow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Fireplace

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Price per night from

$397

The Grafton Lodge

Grafton lodge

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 20

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Price per night from

$2,185

Treehouse

Ludlow house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 16

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Price per night from

$784

The Whimsical Chalet

Mount Holly villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$305

Beautiful VT Getaway w/ Firepit - 5 min to Okemo

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Fireplace

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Price per night from

$345

Okemo Mountain Lodge A-108 Ski In/Ski Out

Ludlow condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Fireplace

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Price per night from

$230

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