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The Perfect Vermont Experience for All Seasons

Dorset house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$287

Mt Green 2-E06

Killington house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$171

Condo on Haystack/Hermitage Ski Mountain

Wilmington condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$344

Vermont Country Lake House

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$287

Mt Green 3-D10

Killington house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$373

“Relaxing and cozy” My husband and I stayed here on our honeymoon, and the barn was a great get-away. It was clean, with great high ceilings, nice wood floors, a full kitchen, a nice living room with tv and books. Our host and hostess at the main B&B; were lovely and cooked delicious breakfasts with extra baked treats. We had a wonderful stay!

Responds fast! avg. 16 minutes

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Price per night from

$251

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

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$258

Casual lux near Hermitage Club & Four Columns Inn

South Newfane villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

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Price per night from

$1,718

Red Acre Cottage in the Green Mountains of Vermont

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$144

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

Killington house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$1,260

“Great Experience” Lori and Gary were Great, and very accommodating. The scenery was spectaculur,and the house is beautiful. Food was great and I loved seeing the Hummingbirds at Breakfast. Can't wait to do this again.

Responds fast! avg. 16 minutes

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Price per night from

$228

Killington area mountain home on 60 acres and surrounded by National Forests

Pittsfield house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$229

6 BR Ski Chalet with Boats in VT Green Mountains

Ludlow chalet

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$373

Walk to ski trials on Okemo! Private Luxury Chalet

Ludlow chalet

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$1,369

Fall dates So Vt Mtn Cabn where memories are made and guaranteed to come back.

Mount Tabor log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 20 minutes

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Price per night from

$235

Suites at Killington: Luxury 2 BR Resort Ski Condo

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$166

5 mins to Mt Snow Free Shuttle Ski Home

Dover townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$229

Trailside Condo at Mt. Snow avail. Memorial weekend @$200/night

Dover apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“A CONDO TO KEEP COMING BACK TO!” We've rented this condo with friends many times in the past several years, and it's one of our favorites. Steve is very pleasant to deal with, the condo is clean, sleeps many people comfortably, and overlooks the mini terrain park/learning area. We've had grandma come along and she loved to watch the kids ski from the balcony. Also on MLK weekend the balcony was the perfect place to view the fireworks. Would highly recommend this unit!

Responds fast! avg. 3 hours 23 minutes

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Price per night from

$401

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$401

Beautiful Mountainside 2 Bedroom 2 Bath Condominium

Dover condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$172

Vermont Log Home On 21 Acres Btwn Okemo/killington

Mount Holly house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$430

Killington Mountain Slopeside Home

Killington house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Ski home at Killington” We've been here for 10 days in late January. Wonderful place. Excellent home. We were two families with 4 aDT, CHD 4 with 6.9, 11 and 14 years. We left and came back home from skiing. We used the heated pool at the sport center. the hot tub ... We skate on the frozen pond. Although we are not accustomed to the cold (-13 F/ -25 C) for being Brazilians, we enjoyed a lot. Thank you!

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Price per night from

$974

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Price per night from

$488

Family Lodge btwn Stratton Mountain & Mt. Snow

Stratton Mountain house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

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Price per night from

$682

Country Farmhouse with Views

Shaftsbury house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$401

Ski Killington Vermont

Killington apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

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Price per night from

$218

Mt Green 2-F06

Killington house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$177

Mt Green 2-C03

Killington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$258

Mt Green 2-F04

Killington house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$205

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$458

Spectacular 50 miles Year Round Mountain View - 3+ BR Townhouse

Peru townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 2 minutes

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Price per night from

$338

Mt Green 2-D01

Killington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$220

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$1,123

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$189

☆ SKI ON & OFF! ☆ Luxury Trailside Townhome! NEW Steam Shower, Hot Tub, Pool

Killington townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 9 minutes

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Price per night from

$126

Mt Green 2-F09

Killington studio

  • Studio
  • 1 bathroom
  • sleeps 4

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Price per night from

$163

RV/Camper rental Randolph VT area

Braintree camper van

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$144

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Price per night from

$572

Viewing 38 of 48
rentals in Rupert

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