Vacation Rentals & Chalets in Killington

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Red Acre Cottage in the Green Mountains of Vermont

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Horse riding Pets allowed

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Price per night from

$144

6 BR Ski Chalet with Boats in VT Green Mountains

Ludlow chalet

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Horse riding Pets allowed

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Price per night from

$373

These homes match some but not all of your filters. Clear all filters

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$489

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$402

INDESCRIBALE Mountain View Getaway! Tons of Amenities!

Shrewsbury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 20

Responds fast! avg. 37 minutes

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$458

Killington/Rutlan 2 Bedroom w/NO Hidden Fees

Mendon house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$217

Clean/Comfortable 1 Bdrm Cabin w/NO Hidden Fees*

Killington house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$194

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$344

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$344

LUXURY, hot tub, private, 6 BR, 3 BA

Killington house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$1,262

Clean/Comfortable 2 Bdroom Cabin w/No Hidden Fees*

Mendon house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$206

Beautiful VT Getaway w/ Firepit - 5 min to Okemo

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$344

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$190

Oma"s Kottage

Ludlow house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 11

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$344

“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!

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$1,835

Killington - FALL IN THE MOUNTAINS...YOU CAN'T BEAT THE VIEWS!

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Horse riding

1 of 2 filters match

Price per night from

$258

RV/Camper rental Randolph VT area

Braintree camper van

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$144

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$688

The Whimsical Chalet

Mount Holly villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$291

Sweet Life

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$367

Hakuna Matata

Bridgewater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$371

Blue Ridge Chalet

Mendon villa

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$281

Sunrise - Bear Ridge C4

Killington condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$406

Pond View Cabin

Chittenden log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$148

Winter Lore

Mendon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$406

Sunrise - W Glade J-1

Killington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$288

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$430

3 Season Cabin - sleeping porch lake trails

Mount Holly log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 1 hour 58 minutes

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$104

Vermont Log Home On 21 Acres Btwn Okemo/killington

Mount Holly house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$430

Perfect Hideaway Cabin - lake, trails, forest, meadows

Mount Holly log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 58 minutes

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$104

Breakaway House - Unit A & B

Killington house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$668

Farmhouse Rustic Lux on 10 acres w/ swimming pond

Bridgewater house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 22

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$746

Vermont Cottage Lake Amherst

Plymouth cottage

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$803

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$402

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

Ludlow apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$402

Bear Run

Killington house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$929

Chestnut Farm

Plymouth townhouse

  • 10 bedrooms
  • 3 bathrooms
  • sleeps 15

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$595

Hawk Landing

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Horse riding, Pets allowed

1 of 2 filters match

Price per night from

$387

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rentals in Killington

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