Stockbridge Vacation Rentals

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The Crooked House
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3BR 2.5BA mountain house w/ sauna near Killington

3 Bedrooms
2½ Bathrooms
4 Guides
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100 reviews
$225 - $500 / night (excl. fees & taxes)
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Heavenly Killington luxury home on Killington Road
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Heavenly Killington luxury home on Killington Road

7 Bedrooms
4 Bathrooms
4 Guides
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83 reviews
$600 - $2975 / night (excl. fees & taxes)
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Kilbourne Lodge︙3BR/2BA+Pets+Fireplace+Boot Dryer
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Kilbourne Lodge︙3BR/2BA+Pets+Fireplace+Boot Dryer

3 Bedrooms
2 Bathrooms
4 Guides
4.91IconIconIconIconIcon
33 reviews
$163 - $979 / night (excl. fees & taxes)
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Killington VT Condo - Mountain Green
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Walk to Snowshed - Remote Work Hub - Hot Tub/Pool

1 Bedroom
1 Bathroom
4 Guides
$137 - $933 / night (excl. fees & taxes)
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Killington Grandview House
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Contemporary Spacious 7br/6.5 bath home near Killington VT

7 Bedrooms
6½ Bathrooms
4 Guides
4.86IconIconIconIconIcon
7 reviews
$1100 / night (excl. fees & taxes)
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Updated Home in Heart of Rutland, Near Slopes
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Updated Home in Heart of Rutland, Near Slopes

4 Bedrooms
3 Bathrooms
4 Guides
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14 reviews
$205 - $499 / night (excl. fees & taxes)
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Cute, Renovated Home on River, Walk to Downtown
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Cute, Renovated Home on River, Walk to Downtown

3 Bedrooms
1½ Bathrooms
4 Guides
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50 reviews
$175 - $250 / night (excl. fees & taxes)
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Owl's Nest
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4 Bedrooms
2 Bathrooms
4 Guides
$265 - $715 / night (excl. fees & taxes)
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Authentic Log Home: Kismet Cabin
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Adventure by day; unwind under starry skies by night. Kismet Properties - central to a mecca of uniquely Vermont experiences.

3 Bedrooms
2 Bathrooms
4 Guides
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12 reviews
$250 - $600 / night (excl. fees & taxes)
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Alpine Apartment Suite
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Relax in a Modern Apartment with a private deck, full kitchen, & convenient location near Sugarbush, Mad River Glen, and Hiking and Biking trails.

1 Bedroom
1 Bathroom
4 Guides
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25 reviews
$101 - $350 / night (excl. fees & taxes)
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Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
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Twinkle Cottage~HotTub~FirePit~Dogs~Volley Ball~Croquet~

1 Bedroom
2 Bathrooms
4 Guides
$350 / night (excl. fees & taxes)
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Cool Haven~Cute Cottage in Plymouth, Vermont.
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1 BR Cottage Fireplace~Lake Views~Hot Tub~Dog Freindly~Private

1 Bedroom
2 Bathrooms
4 Guides
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34 reviews
$300 - $350 / night (excl. fees & taxes)
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Forty Winks Cottage In Vermont
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3 BR~3BA~DogFriendly~FirePlace~HotTub~FirePit~Charming~Cozy~Unique~Vintage~Okemo~Killington

3 Bedrooms
3 Bathrooms
4 Guides
4.98IconIconIconIconIcon
52 reviews
$400 - $600 / night (excl. fees & taxes)
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Vermont Cottage Amherst Lake & Sanctuary
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LakeAmherstRentals~Good Woods Cottage~Okemo Killington~Dog Friendly~Hot Tub~Fire Pit~

4 Bedrooms
3 Bathrooms
4 Guides
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55 reviews
$650 / night (excl. fees & taxes)
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Vermont Cottage~Lake & Sanctuary~Lake Amherst
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Vermont Cottage On Lake Amherst & Sanctuary ~ Pet Friendly ~ Fire Pit ~ Fire place ~ Between Okemo & Killington Areas ~ Route 100

6 Bedrooms
4 Bathrooms
4 Guides
4.98IconIconIconIconIcon
90 reviews
$800 - $900 / night (excl. fees & taxes)
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NirvanaSanctuaryHouse~Fire Place~Okemo Killington
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Nirvana Sanctuary House~Fire Place~Okemo Killington 2 BR 3BA

2 Bedrooms
3 Bathrooms
4 Guides
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31 reviews
$425 / night (excl. fees & taxes)
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Mount Holly Lake & Ski Hideaway
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Mount Holly Lake & Ski Hideaway

4 Bedrooms
2 Bathrooms
4 Guides
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37 reviews
$299 / night (excl. fees & taxes)
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Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
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Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

6 Bedrooms
2 Bathrooms
4 Guides
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107 reviews
$550 / night (excl. fees & taxes)
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Mountain View Manor
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Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

6 Bedrooms
5 Bathrooms
4 Guides
$670 - $2122 / night (excl. fees & taxes)
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2 Bdrm, Upper Level, Okemo, 25 Acre Mtn Playground
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Close to Okemo, 25 Acre Mountain Playground, 2 Bedroom

2 Bedrooms
1 Bathroom
4 Guides
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13 reviews
$200 - $300 / night (excl. fees & taxes)
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