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, 281 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, 124 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, 41 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.

Guest favorite

A large tree with autumn leaves stands prominently beside a gravel driveway. The house is partially visible in the background, and wildflowers with white blooms line the foreground. The sky features a mix of clouds and sunlight, adding to the natural setting.

Home in Oshkosh

4.83 out of 5 average rating, 102 reviews

Jackson Farmhouse

PERFECT FOR ANY FAMILY, CONFERENCE / EVENT ATTENDEE AND YOUR GROUP! Our beautifully restored 100 YEARD OLD farm house is located on Jackson St in Oshkosh giving you quick and easy access to highway 41! **Please note this home is old and has sloping floors and a few drafts** The easy in and out driveway can hold at lease 8 cars if needed during your stay at our comfortable property. After a long day of whatever you may be in town for you'll be able to relax in your own piece of country!

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, 154 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

A well-lit hallway features smooth wooden flooring and white walls. Two framed botanical prints are displayed on the left. A small table with a plant is positioned near the doorway, which opens into a bathroom. Light filters in from the bathroom window.

Apartment in Neenah

4.85 out of 5 average rating, 164 reviews

Cozy and Simple Downtown Space

Enjoy this great space in a quiet safe neighborhood. One car allowed at the property! The space has comfortable beds, provided hygiene products, a smart TV and snacks + beverages. Wake up and enjoy coffee provided by us. Shops and restaurants within walking distance! Visit The Plaza downtown with ice skating, fire pits, a coffee shop and more. Great for a couples getaway. Luxury for a great price! A portion of the proceeds from bookings go to housing evacuees, refugees and veterans.

Guest favorite

The kitchen features modern cabinetry and stainless-steel appliances, with a spacious island at the center. Natural light fills the open living space, which blends the kitchen, dining, and living areas. A comfortable seating arrangement is visible, with a view of the patio through the sliding glass doors.

Home in Brillion

5 out of 5 average rating, 20 reviews

Newly Built Brillion Townhouse

Come & enjoy a newly built townhouse that is fully furnished for an easy stay! Located in Brillion, it is central to Manitowoc, Green Bay, and Appleton (about 25 min to each & 40 min to Lambeau Field!). Enjoy many amenities like zoned in-floor heat, wall air, Zero entry (no steps), attached 2 car garage, patio, park views, open concept w/full & large kitchen, dining & living room. Dual entry full bath, in-unit washer & dryer. Minutes to Ariens Nordic Center. 40 min to Lambeau Field!

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, 180 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.

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, 191 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 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.

Superhost

A cozy living area features two light-colored sofas adorned with patterned cushions. A black coffee table holds a tray with a small vase and a candle, while a soft area rug complements the space. Sheer curtains frame a window, allowing natural light to brighten the room.

Townhouse in Oshkosh

4.82 out of 5 average rating, 50 reviews

Cozy EAA Home • 2BR w/ Firepit • Near Downtown

Perfect EAA base! Just 10 min from the AirVenture grounds with easy shuttle access via UWO. This cozy modern farmhouse-style townhome features a private backyard with firepit and string lights. Walk to Main St bars, coffee, and Farmers Market. Near Menominee Park for lake views, trails, zoo, and beach. Quick drive to Lake Winnebago, Downtown Oshkosh, and Sunnyview Expo Center. Enjoy comfort and convenience in the heart of it all!

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, 134 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