Holiday houses in Stockbridge

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Top-rated holiday rentals in Stockbridge

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

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

Coffee on the Lake

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

4.9 out of 5 average rating, 146 reviews

Guest favourite

The image displays a charming lakeside retreat with a well-manicured path leading from a private pier to the house. Two lounge chairs are positioned on the shore, surrounded by trees. The house features large windows reflecting sunlight, enhancing the serene lakeside view.

Home in Chilton

Family lake retreat w/ hot tub! Amazing sunsets!

Lakeland Retreat has 4 bedrooms, den and plenty of entertaining space! Directly on Lake Winnebago with private pier and AMAZING sunsets! Bring your boat and launch nearby, launch is 5 min away. Our spacious outdoor area with double swing for relaxing by the lake, dining table, firepit and hot tub. Great entertainment space indoors with a living room right off the kitchen with lake views. Cozy up by the fireplace indoors too! Full bar area and pool table in the basement! Great family fun!.

4.91 out of 5 average rating, 67 reviews

Top Guest favourite

Home in Appleton

Appleton Wooded Oasis - Hot Tub-6 Star Hospitality

Relax and enjoy in a beautiful scenic home conveniently located in a quiet wooded neighborhood in Appleton. It has all the elements of being your get away from home. Nearly 3,000 sq. ft. Guests have access to all living areas, modern kitchen, wood fireplace, vaulted ceilings, spacious sunroom, large deck and therapeutic hot tub. Enjoy the scenic backyard with a large deck, 7 person hot tub and fire pit. Five minutes from airport, vibrant downtown, 25 min. to Lambeau. Includes breakfast.

5.0 out of 5 average rating, 185 reviews

Guest favourite

Castle in Cleveland

Castle on a vineyard with hot tub and theater

Stay at one of the most Wishlisted Airbnbs in the world — a castle on a vineyard. Featured in Men’s Journal and on the cover of Haven magazine, The Castle Vineyard is a 20-acre estate built for unforgettable stays. 🍇 Vineyard estate with spa, sauna & wildlife views 🎬 Theater, arcade, PS5 & golf simulator 🍽️ Chef’s kitchen with Viking appliances 🔥 Fire pit, patio & hot tub 🏰 “Felt like royalty… every detail was magical.” 🎉 Entire estate is yours. Ask about our exclusive Tasting Room.

4.99 out of 5 average rating, 178 reviews

Top Guest favourite

A log home with a wooden exterior is surrounded by lush greenery. The front porch is adorned with a small blue umbrella and features a set of steps leading to the entrance. Gravel driveway and flower beds enhance the welcoming ambiance of the property.

Home in Oshkosh

Go and Go

Cozy 2 bedroom Log home. Can sleep 4-6. Across the street from Lake Winnebago. Short walk to park, zoo and boat landing. 6.5 miles to EAA grounds. Off street parking. Close to shopping, restaurants and downtown Oshkosh. Great rental for Air Show, Book now and bring your boat, jet ski, trailer, and fishing gear or just go sightseeing, dining and relaxing. Full kitchen, New Bath. Very comfortable with a great location. Perfect place to stay for family with students at UWO. Book now!

4.88 out of 5 average rating, 223 reviews

Top Guest favourite

Home in Hilbert

State Park A-Frame: Hot Tub, Arcade & Hiking

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 large hot tub, 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.

4.95 out of 5 average rating, 260 reviews

Top Guest favourite

Guesthouse in Oshkosh

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.

4.96 out of 5 average rating, 204 reviews

Top Guest favourite

A charming two-story home features a dark exterior with white trim, surrounded by lush greenery. A covered porch with seating is visible, inviting relaxation. Seasonal decorations adorn the front door, enhancing the welcoming atmosphere of the residence.

Home in Appleton

Cheerful 2+ bedroom home with cozy front porch

Your family will be close to everything when you stay at this centrally-located place. Guests will enjoy this lower level 1881 character home .4 mile to the Fox River. Enjoy the covered porch with your morning coffee. Safe, well established neighborhood on E. South River Street with tree lined streets & sidewalks. You are within walking distance to many restaurants, coffee shops, and 1 mile to downtown Appleton. It is 24 miles to EAA and 29 miles to Packer Stadium.

4.98 out of 5 average rating, 108 reviews

Top Guest favourite

Home in Kaukauna

Modern Comfort & Charm with Historic Flair

Ann's Queen Anne is a historic 2-story home with an updated interior offering comfort, convenience, and style. New furnishings and luxurious features make this an ideal place for a retreat, or a base of operations for exploring the area or attending a Packers game at Lambeau Field. Attention to detail and personal touches will make your stay a unique and special experience. Close to Appleton, Oshkosh, Green Bay, Door County, Manitowoc & Sheboygan/Kohler.

4.99 out of 5 average rating, 114 reviews

Top Guest favourite

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

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

4.94 out of 5 average rating, 156 reviews

Guest favourite

A dining area features a large wooden table surrounded by six wooden chairs, situated on polished hardwood flooring. Natural light enters through two windows adorned with sheer curtains. A wooden accent wall adds texture, while a simple chandelier provides overhead lighting.

Home in Oshkosh

The Parkway Paddle: Walking distance to the lake

Stay within walking distance of Lake Winnebago in the heart of Oshkosh at the ‘Parkway Paddle’. The property is next to Menominee Park, which is surrounded by water and the perfect place to watch the sunset. The park also has a zoo with free admission. The historic home has been upgraded with granite countertops and luxurious lakeside and paddle-boat touches throughout the home.

4.77 out of 5 average rating, 144 reviews

Guest favourite

The home exterior is characterized by a gray siding, complemented by a steep roof and multiple windows. A welcoming front porch is accessed by a set of stairs. Colorful flower beds and planters are positioned around the entrance, adding natural beauty to the landscape.

Home in Oshkosh

Cozy getaway 1 mile from downtown and UWO campus!

2 bedroom home with a living room and dining room, kitchen with appliances, laundry room and Big backyard. (Kid friendly) Grocery store, gas station, and restaurants are less than a mile away. (Within walking distance) Great, clean neighborhood. Only a mile from Menominee park, arena, and other destinations you may want to explore.

4.88 out of 5 average rating, 156 reviews