
Family-friendly vacation rentals in Stockbridge
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Top-rated family-friendly rentals in Stockbridge
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.

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.

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.

Howling Wolf Farm Yurt--A Magical Glamping Retreat
Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

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.

Affordable, private, surrounded by flower gardens
Enjoy the summer in beautiful Vermont. The guest area is the entire main floor of a large house with my quiet second home above. Private entrance, 2 bedrooms, full bathroom with washer and dryer, speedy fiber optic internet. The open kitchen has full sized stove and fridge with good cookware and appliances, adjacent to a large open living area. On a paved scenic road. Go up to Silver Lake for a swim, head out on any of the back roads for a run or a ride.

The Guest House at Sky Hollow
This quiet 120 acre hilltop house on an 1800's farm turned homestead offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Gnome Home Mountain Ski Chalet w/Sauna Killington
Mountaintop Chalet perched in the heart of Green Mountains. Enjoy true mountain living all year long 25m to Killington, White River access minutes from home, abundance of hiking trails, and golf courses. Central to Killington, Rochester, & Woodstock. After your adventures, return to a welcoming & comfortable home with beautiful views from every room, multiple decks, new! fireplace, & sauna, and plenty of special touches to help you unwind and relax.

Black haus: a hip, cool house hidden in a forest.
You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

Suite in the Green Mountains
We have a first-floor,two-room suite with its own entrance in our home, located on an official Vermont Scenic Highway, in the middle of the Green Mountains. The suite has a large sitting room with a kitchenette; a bedroom with queen bed and A/C; and bathroom with tub/shower. NOTE: We have a second, larger unit in our home called "Two-Bedroom Apartment in the Green Mountains".

Apple Hill Cabin at Four Springs Farm
Privately located walk-in camping sites are part of this beautiful working organic farm on a west-facing Vermont hillside. Guests will be dazzled by star-studded skies, treated to spectacular sunsets, and entertained by the two young farm cats. The farm is mosquito free but has millions of fireflies in summer. Have fun exploring. It's nature's playground at her best!!!

"Swiss Charm"- A Beautiful Riverfront Chalet
Nestled comfortably on the banks of the Tweed River just 9 miles North of the Killington Access Road just off Rt. 100, "The Skiers Highway" with Direct Access to VAST Trails. A 2BR 1 BA A-Frame Chalet is the perfect Pet Friendly weekend getaway. Quaintly decorated and well stocked...This is truly a "Home Away From Home".
Popular amenities for Stockbridge family-friendly rentals
Family-friendly home rentals with a hot tub

River House Apartment - Dog friendly

Romantic Treehouse- Hot tub, A/C, 20 Min to KLT

Scandinavian design Chalet w/ private hiking trail

SnowCub Pets Indoor Pool Hot Tub Sauna, FirePlace

Killington area home - 4-seasons & hot tub

Beautiful Spacious Condo at Killington Resort

Private Barn On a Hilltop in Fairlee, Vermont

Killington ski house winter MTbike -new jacuzzi
Family- and pet-friendly home rentals

Fairytale cabin at The Wild Farm

Private Tiny House Retreat

Peaceful Log Cabin in the Woods

My house is your house!

Camping on a Private Pond

Beautiful 1 Bedroom Suite with private entrance

Quaint 1-bedroom cottage on Blue Ledge Farm

Breadloaf Hut. Glamping, hiking, biking, foliage
Family-friendly home rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Comfy ski in/out studio at base of Pico-Killington

Epic Views of the Green Mountains

Ranch at Mendon Mt Orchards

Renovated 1BR, Walk to Lifts, Covered parking

Newly renovated ski retreat at Killington

Private Suite in the Green Mountains

Cozy/Private, close to hospital, i-89
When is the best time to visit Stockbridge?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $571 CAD | $560 CAD | $539 CAD | $407 CAD | $389 CAD | $421 CAD | $427 CAD | $417 CAD | $414 CAD | $431 CAD | $417 CAD | $560 CAD |
| Avg. temp | -6 °C | -5 °C | 0 °C | 8 °C | 15 °C | 20 °C | 22 °C | 21 °C | 17 °C | 10 °C | 4 °C | -2 °C |
Quick stats about vacation rentals that are family-friendly in Stockbridge

Total vacation rentals
Explore 50 vacation rentals in Stockbridge

Nightly prices starting at
Stockbridge vacation rentals start at $126 CAD per night before taxes and fees

Verified guest reviews
Over 2,050 verified reviews to help you choose

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Stockbridge vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Stockbridge rentals

4.9 Average rating
Stockbridge stays are highly rated by guests—averaging 4.9 out of 5!
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