Vacation rentals in Stockbridge

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Top-rated vacation rentals in Stockbridge

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Guest favourite

Cabin in Royalton

4.99 out of 5 average rating, 174 reviews

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

Nov. 28 – Dec. 5

$240 CAD per night

Guest favourite

Guest suite in Royalton

4.96 out of 5 average rating, 180 reviews

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 and even a few extras like farm fresh eggs in the fridge and hot chocolate. 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!

May 1 – 8

$180 CAD per night

Superhost

Chalet in Stockbridge

4.85 out of 5 average rating, 114 reviews

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.

Oct. 4 – 11

$253 CAD per night

Guest favourite

Condo in Killington

4.95 out of 5 average rating, 129 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

Jul. 22 – 29

$211 CAD per night

Guest favourite

Apartment in Stockbridge

4.88 out of 5 average rating, 160 reviews

Rustic 64 Acre Woodland Haven on a Beautiful River

Peaceful 64 acre secluded retreat located in a forested valley, surrounded by a beautiful river, accessed by a private bridge, with private swimming holes and river beaches. Private full level apartment in a two floor house, with forest views from every window. Perfect for river swimming in Summer, leaf-peeping in the Fall, and winter skiing. Connected to VAST and VASA trails system. Appalachian Trail access. Two miles to the Wild Fern, 7 miles to I-89. 20 minutes from Killington.

Sep. 14 – 21

$281 CAD per night

Guest favourite

Guest suite in Royalton

4.96 out of 5 average rating, 165 reviews

Bluestone Farm

Bluestone Farm is a private second story guest suite with all the amenities. High ceilings, quiet, on a Vermont back road with 70 plus acres of land and a pond. You have a full working kitchen; private bathroom with large walk in shower; living room, and private bedroom with a queensize mattress. Nearby to Vermont Law School, 40 minutes to Ben and Jerry's, Woodstock, and Montpelier. 2 miles from Worthy Burger and a quick ride to Interstate 89 for many other Vermont attractions.

Jun. 12 – 19

$175 CAD per night

Guest favourite

Apartment in Pittsford

4.99 out of 5 average rating, 117 reviews

Waterfront cottage walk-out suite.

Private entrance suite overlooking Burr Pond. Conveniently close to Mountain Top Inn & Resort (3.7 miles), Killington/Pico ski resorts and Rutland. Swim, kayak, bike and hike in the warmer weather. Take advantage of more than 12 miles of the Pittsford Trail Network. The serenity of country living coupled with the amenities of Rutland! We’re on a short dirt road off of a steep hill. Front wheel or 4 wheel drive vehicles with good all season or snow tires required in the winter.

May 14 – 21

$166 CAD per night

Guest favourite

Cabin in Randolph

4.95 out of 5 average rating, 192 reviews

Secluded Log Home on 109 Acre Natural Wonderland!

Enjoy our remote, easily accessible, immaculate new log house, set in nature on 109 acres. Pond, woods, fields and trails; with high speed internet and smart TV! Sleeps 6, including a queen bed, 2 bunk beds, and a sleep sofa. Fully equipped kitchen, including a full-sized refrigerator, microwave, Keurig coffee maker and many other amenities. Screened in porch. Views from every room! In the heart of the ski corridor. Explore the trails, and the meditation yurt when available!

Aug. 10 – 17

$243 CAD per night

Guest favourite

Guest suite in Bethel

4.97 out of 5 average rating, 137 reviews

Two bedroom. Separate enterence.

Please be advised that during winter months you may need to walk up Winterberry lane and our driveway if you do not have an AWD vehicle with good snow tires. Two bedroom apartment in the heart of Vermont. Snowmobile trail located off lane. Snowshoe, hike, or mountain bike from the door. Quiet private location with separate entrance and parking onsite. Ramp to access apartment, with stair free access. Pond, views and located in the center of the state, a great place to start!

Aug. 25 – Sep. 1

$212 CAD per night

Guest favourite

Home in Bethel

4.84 out of 5 average rating, 129 reviews

Hike, run, swim or cycle in beautiful Central VT

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.

Oct. 20 – 27

$200 CAD per night

Guest favourite

Cabin in Rochester

4.95 out of 5 average rating, 391 reviews

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.

Nov. 10 – 17

$217 CAD per night

Guest favourite

Cottage in Windsor

4.97 out of 5 average rating, 318 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins.

Nov. 18 – 25

$217 CAD per night