Holiday houses in Stockton

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Top-rated holiday rentals in Stockton

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Guest favourite
A park model home is positioned on a stone terrace, surrounded by lush greenery. Large windows offer expansive views of the surrounding landscape. A wooden deck with seating is visible, extending the living space outdoors, with a tranquil atmosphere conveyed by the scenic backdrop.
Cabin in De Soto
4.96 out of 5 average rating, 118 reviews

Paradise Point sleeps 2 Hot Tub

1 bedroom 1 bath with loft. Cozy home where you can see Paradise. This memorable place is anything but ordinary. Views for miles of the Mississippi River, bluff tops and you can soar with the Eagles. What a place to relax in the newly added hot tub while you enjoy the view in what is call "God's Country". This is promised to be a one of a kind view. The Deck with comfortable outdoor seating Located in the heart of WIsconsin's Driftless Region. New workout center for all our guest to use.

Top Guest favourite
An open kitchen and living space feature a large wooden countertop with three metal stools. The room is illuminated by a stylish chandelier, with a brick accent wall providing character. Large windows allow natural light to fill the area, showcasing the hardwood floors.
Loft in Winona
4.99 out of 5 average rating, 783 reviews

Penthouse Retreat-Near Downtown Winona!

Hi! This beautiful loft is conveniently located in the heart of Winona MN! Only a few blocks from the downtown and in close proximity to many other attractions Winona has to offer such as: Coffee, restaurants, a wine bar, Winona State University, Mississippi River, Lake Winona, hiking trails, Shakespeare Festival, Minnesota Marine Art Museum, and much more! Please allow us to make your next extended stay in beautiful Winona a memorable one! * MUST CLIMB STAIRS TO UNIT- LOCATED ON THE 3RD LEVEL

Top Guest favourite
A spacious dining area features a large black table surrounded by six teal chairs, placed on a striped rug. A vibrant window seat adds color, while a chandelier hangs above, contributing to the room's inviting ambiance. The kitchen can be seen in the background.
Bungalow in Winona
4.98 out of 5 average rating, 263 reviews

*Prairie Island Bungalow with Water Access*

Welcome to Prairie Island Bungalow (PIB)! Located on Prairie Island in Winona, this home provides the perfect, quiet getaway for work or play, and is your gateway to outdoor adventure in the Winona area. River access is available on our private dock next door! With thoughtful amenities including a fully-stocked kitchen (with coffee and tea!), plush linens, Smart TVs, games and books, a fire pit, snowshoes, and kayak and canoe rentals; we invite you to simply show up and enjoy your stay at PIB!

Top Guest favourite
A cozy living room is showcased, featuring a wood-burning stove positioned on a stone base with stacked firewood. A light-colored sofa is seen, with a decorative floor lamp nearby. The walls are painted in neutral tones, enhancing the room's relaxing ambiance.
Cottage in Winona
4.91 out of 5 average rating, 104 reviews

Quiet Cottage in the Valley with Sauna

Nestled in the bluffs of Winona, Minnesota, The Driftless Retreat is a cottage in the valley just one mile from Saint Mary's University and a 10 minute drive to downtown Winona and the Mississippi River. The cottage features a private front and back entrance, large backyard, and woodburning fireplace. Our hope is that The Driftless Retreat is just that, a retreat away from the every day. We believe that every detail matters and take pride in making your time here relaxing and enjoyable.

Guest favourite
A spacious living room features a modern fireplace with a black brick surround. Comfortable seating options include a gray sofa and colorful armchairs. A wooden coffee table sits centrally, while a large television is mounted on the wall. Light filters in through sliding glass doors, enhancing the room's inviting ambiance.
Cottage in Stoddard
4.91 out of 5 average rating, 320 reviews

Stylish 1 bedroom cottage on the Mississippi River

This unique place has a style all its own. Conveniently located by the Mississippi River and highway 35. The place gives you a cabin feel close to La Crosse! 15 minute drive to downtown La Crosse and 3 miles North of Stoddard puts you in a great central location for the area. Mt. La Crosse is super close to enjoy skiing/snowboarding. Goose Island is 5 minutes away. Great spot for bird watching, fishing, kayaking, boat launches, hiking or frisbee golf. Pets are welcome. No cleaning fee!

Top Guest favourite
A serene view of the Mississippi River is captured, featuring a boat and a paddleboarder on calm waters. Lush green trees line the riverbanks, while gentle hills rise in the background under a cloudy sky.
Home in Fountain City
4.95 out of 5 average rating, 147 reviews

River Road Abode: breathtaking river views

Entire 2 bedroom home with amazing views of the Mississippi from every room in the house. 3 unique decks to watch birds, barges, boats, bluffs and trains. Out front you can wave at people passing by on the Great River Road. Located near WI and MN state parks, wineries, breweries, and restaurants. Adventure outdoors or stay in and watch all the Mississippi has to offer from the private patio and decks. Trains pass by property day & night. Home is well insulated & ear plugs are provided.

Top Guest favourite
A wooden sauna is positioned in the center of a rustic room with exposed beams and corrugated metal walls. Two wooden rocking chairs sit nearby. Light enters through several windows, and a basket is placed on the floor, enhancing the inviting, serene environment.
Home in Stockholm
4.96 out of 5 average rating, 274 reviews

Bogus Valley Holm Country/Farm Pepin/Stockholm

Come to the country and enjoy lodging at quiet Bogus Valley Holm. Located in picturesque Bogus Valley, between Pepin and Stockholm Wisconsin. This vintage home farmstead on 4 acres, was built in the mid 1850s and has old world character architecture with the comforts of modern day amenities. The southern exposure enclosed front porch is the favorite gathering spot for most everyone that has stayed in the home. This 2 bedroom 1 1/2 bath property has potential for sleeping up to 8 guests.

Guest favourite
A spacious modern barn-style cabin is depicted against a clear blue sky. A well-maintained grassy area surrounds the structure, featuring multiple windows and a basketball hoop mounted on the side. Two cupolas adorn the roof, contributing to the building's distinct character.
Barn in Peterson
4.96 out of 5 average rating, 113 reviews

Big Buck Inn

Brand new heating and air unit installed in 2025! Cabin is upstairs in a modern barn. Beautiful panoramic views. Spacious 2 BR/1 BA open concept with a full kitchen. Country cottage decor combined with an avid sportsman's touch. Patio with a bonfire area & private grill. Minutes to trout streams, dining, shopping, bike trail, Lanesboro and Peterson. Enjoy the morning turkey gobbles, pheasant kackles, or the afternoon visit of a whitetail deer strolling through!

Top Guest favourite
Apartment in Winona
4.95 out of 5 average rating, 276 reviews

2nd Floor Retreat - 7 Blocks from WSU

Our one-bedroom apartment is perfect for two guests. * Spacious bedroom with queen size bed, couch and workspace * Fully kitchen with oven, refrigerator, microwave + coffee/tea station * TV, board games and books * All amenities needed for a comfortable stay * Walking distance to WSU and Cotter * Your own washer dryer in the apartment * Easy self-check-in process We want you to love your time in Winona and are here to make your stay as pleasant as possible.

Guest favourite
A spacious bedroom features a wooden ceiling and warm-toned walls. A large window allows natural light, while a cozy quilt covers the bed. A decorative rug is placed on the wooden floor, and a dresser with a mirror adds functional charm to the room.
Cabin in Hixton
4.91 out of 5 average rating, 546 reviews

Living Waters Cabin Getaway

Stunning 92 acre property. Fishing, swimming, hiking, biking, birding, campfires all in an atmosphere of the great outdoors. Spacious bedroom overlooks acres of wooded scenery and landscapes of the rolling hills of Western Wisconsin. Owners home is located approx. 200 ft from cabin. A 2.5 car garage separates buildings. Second Airbnb is located approximately 200 feet from Cabin however no shared areas and completely private and separate from each other.

Top Guest favourite
A spacious living area is highlighted by a large couch and two armchairs, set around a coffee table on a patterned rug. A television is positioned on a dark cabinet, while large windows provide ample natural light, framed by original molding.
Loft in Lanesboro
4.92 out of 5 average rating, 324 reviews

High Court Loft-the Judge's Chamber

High Court Loft is on the 3rd floor above High Court Pub on Lanesboro's historic Main Street. The large open space features a wall bed, kitchen w/1 pot induction stovetop, convection toasteroven, coffeemaker, fridge & microwave. The Loft is great for lounging or entertaining small groups. Large original windows open to a wonderful view of the lively downtown. In addition to the bed there is a queen deluxe airbed. Pets not allowed.

Top Guest favourite
The exterior features a two-story structure with a wooden facade and large garage doors. A set of stairs leads up to the entrance, surrounded by natural stone landscaping and colorful flowers. Trees and greenery provide a serene atmosphere.
Condo in Rochester
4.98 out of 5 average rating, 192 reviews

Cedar Loft is a tranquil retreat

If you are looking for a quiet retreat w/private entrance outside the city, you are home. Trees are outside every window with palpable serenity yet is still an easy ten-minute drive to downtown Rochester. This is a family-friendly place with crib and changing table. This is not a party house. It has a kitchenette so we will provide information to restaurants and grocery stores within 5 minutes.

Popular amenities for Stockton holiday rentals

  1. Airbnb
  2. United States
  3. Minnesota
  4. Winona County
  5. Stockton