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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.

Guest suite in 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
Chalet in 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.
$141 per night
Treehouse in Stockbridge
Treehouse-hot tub, 20 min to Killington Powder
New treehouse was built by me with my own two hands during the pandemic. The architect styled design is one of a kind with huge windows. Radiant Heat, custom bathroom/kitchen. My grandparents once owned and operated a dairy farm in the area and I want to share this treehouse and surrounding area with my guests. Ski or Ride in only 20 min to Killington and resorts. My treehouse is located on the historic ski highway with Killington-20 min, Pico, Okemo, Sugarbush, Saskadena Six, and Stowe.
$348 per night

Stay near Stockbridge's top sights

Photo of Tozier's Restaurant
Tozier's Restaurant17 locals recommend
Photo of Clear River Tavern
Clear River Tavern26 locals recommend
Photo of Clear River Inn
Clear River Inn9 locals recommend
Photo of Swiss Farm Inn
Swiss Farm Inn10 locals recommend
Photo of Wild Fern
Wild Fern13 locals recommend
Photo of Riverside Farm
Riverside Farm3 locals recommend

Other great vacation rentals in Stockbridge

Cabin in Stockbridge
Peaceful Mountain Home with Sweeping Views
$171 per night
Chalet in Stockbridge
"Swiss Charm"- A Beautiful Riverfront Chalet
$165 per night
Chalet in Stockbridge
Gnome Home Mountain Ski Chalet w/Sauna Killington
$193 per night
Rental unit in Hancock
Carriage House
$77 per night
Cabin in Pittsfield
Central to VT Fun | Gigabit Wi-Fi | 8 mi. to Ski
$157 per night
Home in Stockbridge
Ski, snow mobile, hiking, fun on slopes & trails!
$145 per night
Home in Stockbridge
Escape to Vermont
$195 per night
Cabin in Pittsfield
8 mi. to Killy/Pico | Gigabit Wi-Fi | Mtn. Views
$180 per night
Chalet in Stockbridge
Private Luxury House- Hot Tub,Steam Room,Fireplace
$375 per night
Home in Bethel
Hike, run, swim or cycle in beautiful Central VT
$92 per night
Condo in Killington
🎿Cozy Fireplace Condo-Mins. to Everything 🚵
$122 per night
Cabin in Pittsfield
Tiny Vermont Cabin!
$175 per night
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  2. United States
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  4. Windsor County
  5. Stockbridge