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Vacation rentals in Stockbridge

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Top-rated vacation rentals in Stockbridge

Guests agree: these stays are highly rated for location, cleanliness, and more.

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SUPERHOST
Treehouse · Stockbridge
Treehouse-Hot Tub,White Rivertubing,A/C,Killington
My treehouse was built by me with my own two hands during the pandemic. The architect styled design is one of a kind. My grandparents once owned and operated a dairy farm in the area. I want to share this treehouse and surrounding area with my guests. Tube and kayak the White River across the street and 20 min to Killington downhill biking and skiing. My treehouse is located on the historic ski highway with Killington-20 min, Pico, Okemo, Sugarbush, Saskadena Six, and Stowe.
$451 per night
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Entire guest suite · Stockbridge
Studio Suite with Vermont Style & Amazing Views
Central to Killington, Pico & Sugarbush Ski Areas. Breathtaking views. Features all Vermont has to offer in any season - Golf, Downhill & X-country Skiing, nearby VAST trails, Snowshoeing, Hiking, Trail & Road Biking. Unit is en suite w/sitting area, dining table/desk, kitchenette (no stove). Shower and toilet with ADA bars. Handicap accessible. Large closet, dresser. Streaming TV/DVD/VHS, selection of games, discs and tapes. 2 entrances - public and private. Stone patio and fire pit. Quiet.
$129 per night
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SUPERHOST
Entire chalet · Stockbridge
Vermont Chalet
Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.
$146 per night

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Other great vacation rentals in Stockbridge

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Entire rental unit · Stockbridge
Rustic Vermont Getaway
$151 per night
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SUPERHOST
Entire cabin · Stockbridge
Peaceful Mountain Home with Sweeping Views
$190 per night
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SUPERHOST
Entire chalet · Stockbridge
"Swiss Charm"- A Beautiful Riverfront Chalet
$126 per night
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SUPERHOST
Tent · Stockbridge
Delightful Vintage Inspired Glam Camp
$185 per night
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SUPERHOST
Entire home · Stockbridge
Escape to Vermont
$230 per night
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Entire cabin · Pittsfield
Tiny Vermont Cabin!
$182 per night
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Treehouse · Bethel
Crooked Maple Treehouse
$200 per night
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Entire condo · Killington
🎿Cozy Fireplace Condo-Mins. to Everything 🚵
$67 per night
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SUPERHOST
Entire home · Stockbridge
Ski, snow mobile, hiking, fun on slopes & trails!
$183 per night
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SUPERHOST
Entire rental unit · Pittsfield
Peaceful Pittsfield Retreat
$81 per night
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SUPERHOST
Entire home · Rochester
Black haus: a hip, cool house hidden in a forest.
$135 per night
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SUPERHOST
Entire home · Bethel
Vermont private retreat with gorgeous views.
$149 per night
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