
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.

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.

Private Guest Suite on 155 Acre Royalton Town Farm
1 Bed, 1 Bath apartment attached to historic farm house. This cozy space is the perfect spot for a weekend getaway or a long family vacation on a historic Vermont Farm. Equipped with all the linens and dishes you will need. Close to I-89 and 30 minutes of Ski Resorts like Saskadena Six. Property of 155 acres has trails, sledding hills and our farm animals you can enjoy. Check our reviews, you won't be disappointed!

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".

Bright Ski on/off Condo Full Kitchen-Free Shuttle!
Updated Ski on/off at the base of Pico overlooking the mountain! FREE Shuttle to Killington right downstairs. Roll out of bed, walk to the lift and finally get first tracks! Or, let yourself relax and just watch those getting first tracks from the comfort of the private balcony overlooking the trails!
Popular amenities for Stockbridge family-friendly rentals
Family-friendly home rentals with a hot tub

Scandinavian design Chalet w/ private hiking trail

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST

Killington area home - 4-seasons & hot tub

Dog-Friendly/Spa Onsite/Pool/Wine Bar

Beautiful Spacious Condo at Killington Resort

Private Barn On a Hilltop in Fairlee, Vermont

Newly renovated ski retreat at Killington

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

Moon Valley Country Retreat no clean fee pets yes

Fairytale cabin at The Wild Farm

Casita Cabin -Sun drenched cozy cabin on homestead

Earthen Yurt in Green Mtn Wonderland

Yurt In The Woods - Private Refuge

Camping on a Private Pond

Private Modern Cabin w/View of Fields, Hills

Serene Bus Getaway Among Rolling Farm Land
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

Cozy, spacious, 3 bedrooms, 4 beds, swimming pool.

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

Modern Killington Farmhouse Condo: Close to Resort

Charming 3 Bedroom 2 Bath Ski Home/Off

Private Suite in the Green Mountains
Quick stats about vacation rentals that are family-friendly in Stockbridge
Total rentals
50 properties
Nightly prices starting at
R1,559 ZAR before taxes and fees
Total number of reviews
2K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi
Destinations to explore
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- Pet-friendly rentals Stockbridge
- Rentals with a washer and dryer Stockbridge
- Rentals with a fireplace Stockbridge
- Rentals with a patio Stockbridge
- Rentals with outdoor seating Stockbridge
- Rentals with a hot tub Stockbridge
- Rentals with a fire pit Stockbridge
- House rentals Stockbridge
- Family-friendly rentals Windsor County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
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