Vacation rentals in Stockbridge

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Top-rated vacation rentals in Stockbridge

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Top guest favorite

The A-frame cabin is framed by lush greenery and colorful landscaping. A welcoming pathway leads to the entrance, featuring a spacious deck. The cabin's dark exterior contrasts with the surrounding trees, creating a serene and private atmosphere.

Cabin in Elkhart Lake

4.99 out of 5 average rating, 289 reviews

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

Guest favorite

The setting sun casts warm hues across the water, creating a serene view. Waves gently crash against a rocky shoreline, with water splashing over smooth stones. The sky exhibits a blend of oranges and blues, reflecting the tranquil atmosphere by the lake.

Home in Hilbert

4.88 out of 5 average rating, 129 reviews

Coffee on the Lake, Firepit, 35 min to Green Bay

Large 3-story home directly on northeastern Lake Winnebago, 1.5 hours N of Milwaukee and Madison airports, 3 miles N of Chicago. Stunning views of the lake. Open main area with natural light throughout. Large driveway. Games/books/cards/color/ping-pong. Two steps into house. Main floor bedroom includes walk-in shower. Flat yard with fire pit facing lake. Sunflowers provided for bird feeders. No pier available but boat launch < 1 mile at Calumet County Park. Seven miles to High Cliff State Park.

Top guest favorite

An aerial view showcases the expansive green fields of The Farm, framed by a large red barn and the homestead structure. The nearby farmland stretches towards Lake Winnebago, with patches of seasonal crops and scattered trees offering depth to the serene landscape.

Farm stay in Chilton

4.98 out of 5 average rating, 44 reviews

The Farm Unique Rural Lodging

Your accommodations are the entire second floor, with a private entrance and deck to enjoy the sunrise or just relax. The Farm is peaceful offering access to our 100 acres. Our suite has three separate bedrooms, a common area, a micro kitchen and private bathroom. We have a 6 guest limit with a 4 adult max. Published pricing reflects the cost for two guest, each guest after two has a $20 nightly fee. We have a no pets, no smoking or vaping policy. Booking guest must be present during stay.

Top guest favorite

An aerial view of a modern cabin showcases a spacious patio area with outdoor seating and a hot tub. Lush greenery surrounds the property, with a gravel driveway leading to the entrance. The cabin features large windows that allow for ample natural light.

Cabin in Cascade

5 out of 5 average rating, 161 reviews

hot tub and sauna on 5 private acres

Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your inspired getaway awaits!

Guest favorite

An A-frame structure is set against a colorful sunset, featuring a welcoming entryway and large windows. A hot tub is positioned on a deck next to the home. Two adirondack chairs are placed on the lawn near a smokeless fire pit on a tree stump.

Home in Hilbert

4.94 out of 5 average rating, 186 reviews

State Park Getaway with Hot Tub & Arcade

This fully remodeled A-Frame is walking distance to hiking trails and has views of Lake Winnebago. The outdoor enthusiast will find endless opportunities for adventure (canoeing, hiking, fishing, snowshoeing, biking) at High Cliff State Park. Take in the forest views from your private backyard with a fire pit, or relax on the private deck with stunning views of Lake Winnebago. Create memories with the private hot tub, giant chess board, arcade, and huge selection of games.

Superhost

A spacious lakefront deck offers multiple seating options, including wooden benches and Adirondack chairs. A clear view of the lake is provided, with gentle waves visible in the distance. String lights are hung along the railing, adding a subtle ambiance to the outdoor space.

Home in Chilton

4.8 out of 5 average rating, 5 reviews

New! Lake Front|PrivateDock|Kayaks&Paddleboards!

Enjoy Lake Winnebago at this cozy newly furnished lakefront home. It sleeps 7, and includes a fully stocked kitchen. Enjoy the deck facing the lake with chairs and a propane grill—perfect for outdoor meals or a cup of morning coffee from the coffee bar! Spend your days kayaking, paddleboarding, swimming, or fishing from the private dock. Just 15 minutes from Chilton and under an hour from Green Bay, it’s a perfect spot for families or friends to relax and enjoy the lake!

Top guest favorite

The living room features hardwood floors, a plush gray couch, and an accent chair beside a window. A TV sits atop a wood console, complemented by decorative wall art and houseplants. Sunlight brightens the space, enhancing the colorful area rug.

Apartment in Kaukauna

4.98 out of 5 average rating, 127 reviews

Charming 1BR Artist's Perch - Heart of the Valley

Private 2nd floor walk-up on dead-end overlooks wooded ravine & features modern, updated decor in a beautiful old house. Hardwood floors, screened porch, entry/workspace, kitchen/dinette, living room, bathroom w/clawfoot tub/shower. The bedroom has a cozy loft. Close to downtown, library, nature center & recreational trail system. Situated 8.5 mi E of Appleton, 30 mi NE of Oshkosh, 30 mi SW of Green Bay (only 20 mi to Lambeau Field!), and 60 mi NW of Sheboygan/Kohler.

Guest favorite

The cottage features a long, metal-roofed exterior with gray siding and contrasting purple shutters. Lush greenery surrounds the home, including decorative flower beds. A paved pathway leads to the entrance, highlighting the spacious yard. Sunlight enhances the bright and welcoming appearance.

Guesthouse in Oshkosh

4.95 out of 5 average rating, 194 reviews

Cottage on Lake Winnebago

Furnished Cottage on Lake Winnebago with beautiful sunrises. 1 bedroom with queen bed. There is plenty of space for air mattresses in common areas. 1 queen air mattress available. One bath, full kitchen fully stocked with dining area, bring your own food to prepare. Bring your water toys or boat, launch nearby and dock access in warmer months with great fishing. Winter months, bring your snowmobile, trails nearby. Great ice fishing when lake is frozen and ice is safe.

Top guest favorite

A spacious dining area is illuminated by natural light from large windows. A wooden table with six chairs is centered in the room. Decorative items, including wall art and a wreath, are displayed on the walls, contributing to the charming ambiance.

Home in Oshkosh

4.91 out of 5 average rating, 225 reviews

Charming Spacious 2BDR by Downtown/Menominee/Lake

This historic and charming home is located just one block away from Menominee Park and Lake Winnebago. Menominee parks offers amusement rides, the Zoo, asphalt trails, boat tie ups, casting dock, historical interest, fishing, ice rink, picnic areas, large playgrounds, baseball fields, soccer fields, tennis/ pickle ball courts, and volley ball courts. The home boasts a lot of character and has all the amenities to make your stay comfortable and memorable.

Top guest favorite

A relaxing living area features a stone fireplace as its focal point. Comfortable seating options, including a leather chair and a spacious sofa, are arranged around a rustic coffee table. Large windows allow natural light to fill the space, with glimpses of the surrounding scenery.

Cottage in Fond du Lac

4.99 out of 5 average rating, 287 reviews

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

Guest favorite

The exterior of a two-story house is shown, featuring a porch and a well-maintained lawn. Large windows are visible, offering natural light to the interior. Surrounding trees provide shade, and a pathway leads to the entrance, enhancing accessibility.

Apartment in Oshkosh

4.86 out of 5 average rating, 222 reviews

No Cleaning Fees! 2 Bedroom Apartment By The Lake

We’re transparent with our pricing, that’s why we don’t have cleaning fees! The price you see is the price you pay (local taxes still apply). Come stay near the heart of Oshkosh - you’ll be on the second floor with views of Lake Winnebago. If you need anything during your stay we live on-site and are only a message away. Don’t worry though, the units are completely separated so you’ll have all the privacy you desire during your stay.

Top guest favorite

A serene lakeside view showcases the vibrant hues of a sunset over Lake Winnebago. Silhouetted trees line the shore, with the water reflecting the warm colors of the evening sky. The grassy foreground adds a natural element to the picturesque scene.

Cottage in Fond du Lac

4.93 out of 5 average rating, 137 reviews

The Beach House

Cute year round home with fantastic evening sunsets on the East shore of Lake Winnebago. Enjoy the lake life with this 3 bedroom, 1.5 bath, private beach and pier, located on a private beach road and a close drive to restaurants in the surrounding area. Ideal for Walleye Weekend, EAA Convention, Road America, Green Bay Packer games, Wisconsin Badger games, Milwaukee Brewer games, Ryder Cup and more