Holiday houses in Stockbridge

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to

Value · Location · Bathroom

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.

Family · Value · Accuracy

1800s Farmhouse with River Access. Private w/ Land

Enjoy a relaxing stay at this 1800s farmhouse situated on 13 acres of land along the White River. The property has several trails to explore as well as a path to a swimming hole in the river for warmer months. The farmhouse has modern updates to be a warm family friendly space. The kitchen is equipped with a stove and lots of pantry space. The interior is very open with two separate lounge areas and the coziest fire place. Premium bedding and mattresses adorn each of the 3 beds in the home.

Location · Family · Nearby

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.

Location · Family · Kitchen

Comfortable 3 Bedroom King size Master w/ En suite

This is a 3-bedroom rural home with a King size plush mattress in the master bedroom with En Suite bathroom which features a modern single vanity sink and a stall shower. The second bedroom located next to the master bedroom has a twin xl size bunk bed, the third bedroom has a queen-size bed. A unique feature is the pool table and big screen TV in the living room area which is open to the kitchen which has granite countertops and stainless farmhouse style sink. New GE front load Washer+Dryer.

Location · Family · Hospitality

Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! Winter: MUST have AWD/4x4 for winter access on dirt road and driveway. Snow tires recommend. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the beauty Vermont has to offer!

Value · Location · Access

Trailside Retreat: Hike & Bike From Your Doorstep

Airbnb Top 10% Guest Favorite - Ride & Hike the Green Mountain Trails from your door. Location: 5 mins to Green Mountain National Golf, 15 mins to Killington Resort. 1 minn to Village Green Stores. The Space: Modern retreat with stunning mountain views. Two separate living rooms offer privacy for families. Amenities: River swimming access, hiking and mountain biking from your door. Fast Fiber-optic Wi-Fi, secluded, quiet setting. Reliable, 5-star hospitality in the heart of Vermont

Family · Location · Amenities

Escape to Vermont

Welcome to the Red House at Stony Brook! This remodeled 1800's farmhouse offers peace, solitude and comfort in Vermont's national forest. Gaze at stars from the bedroom window and decompress in the mountains. Or, set out for a day of cycling, hiking, skiing and exploring all Vermont has to offer. A chance to experience wildlife, such as moose, birds, bears, turkeys and more. Nearby are Killington Mtn, Sugarbush, famous cycling roads, and several of VTs world renowned eateries and breweries.

Location · Value · Comfort

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

Location · Family · Hospitality

Ski, snow mobile, hiking, fun on slopes & trails!

Cozy 2-bedroom house at the bottom of the mountain with covered front porch. Full access to house, porch, and private yard, including full kitchen with gas stove, pots, pans, and utensils. Grilling area for portable grills. Main heat is propane furnace, with pellet stove for heat and ambiance. Washer/dryer. 25 min drive to Killington Ski Resort. Snowmobilers can access the VAST trail from the property! Well water has slight sulfur smell from high iron, but safe to drink and shower with.

Family · Value · Accuracy

Riverfront Retreat in Stockbridge

3-bed hideaway nestled between Little Stony Brook and the White River, just off Rt 107 in scenic Stockbridge, VT. Watch bald eagles soar down the valley and fall asleep to the sound of the river. Year-round fun: tube the White River from your backyard, toast s’mores, nap in the shaded hammock, or stargaze from cushioned loungers. Ski Killington, Pico, or Sugarbush (20–40 min). Hike Green Mountain trails (15 min). Peace, comfort, and adventure—your perfect riverside retreat.

Family · Location · Barbecue

RZEKA Cottage: Riverfront home in the Green mts.

Welcome to Rzeka Cottage! Enjoy a stylish experience at this riverfront home in the Green Mountains. Centrally located near multiple mountains including Killington, Pico, Whaleback & Okemo. After hitting the slopes, unwind in the hot tub with tranquil sounds of the river in the background. Explore the fish hatchery, neighboring towns, Silver Lake in Barnard, endless hiking trails and more. Whether you’re looking for relaxation or adventure, you’re sure to find it here.

Value · Location · Laundry