Holiday rentals in Richmond

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Top-rated holiday rentals in Richmond

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

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Guest favourite
A vibrant sunset casts shades of pink and purple over calm waters, with silhouettes of hills in the background. A group of people is gathered on a wooden dock, with a boat covered in a tarpaulin nearby. Trees frame the scene, adding to the natural beauty.
Cottage in La Crosse
4.87 out of 5 average rating, 378 reviews

Sunsets on the Edge

My place is 10 minutes from downtown La Crosse, close to the airport, but you'll feel a world away. You’ll love my place because of the peace and quiet, but mostly THE VIEWS. All the modern conveniences of dishwasher, microwave, shower and stove/fridge, washer & dryer. You'll never see the same sunset! My place is good for two people or solo adventurers.Full list of amenities available, but worth noting here that coffee is NOT provided. There is a drip coffee maker, as well as a spot for kpods.

Guest favourite
An open, airy great room features a high ceiling with recessed lighting and large windows, providing ample natural light. A stone fireplace serves as a focal point, while a spiral staircase leads to a loft area. Comfortable seating is arranged around a central coffee table.
Barn in Dakota
4.89 out of 5 average rating, 118 reviews

Renovated Barn Sure To Impress w/ Loft & Game Room

Live your best life with a stay you won't forget! Originally built in the 1920's, this recently updated barn sleeps 13 & features full kitchen, coffee bar, spiral staircase to access loft overlooking great room with floor to ceiling stone fireplace, game room with wet bar, two 70" TV's, 2 bathrooms, laundry with washer & dryer, office space, free wi-fi, & off street parking. Conveniently located a mere block from the mighty Mississippi, boat landing, & only 10 min to La Crosse & 15 min to Winona

Top guest favourite
The exterior view of the home features a large deck supported by white railings, with a front entrance visible below. Dark clouds intermingle with patches of blue sky, and tall green shrubs are positioned in the foreground, providing a natural frame for the house.
Home in Trempealeau
4.91 out of 5 average rating, 44 reviews

Charming home with views of the Mississippi River

Bring your whole family to this charming river town for boating, hiking, biking, vineyards, apple orchards and more. This open concept home is a great gathering place in spring, summer, fall and winter. Everyone can find their place with a full sized kitchen, dining room, living room, family room, game room, large deck over looking the Mississippi, bedroom, and bathrooms. The home is close to the Trempealeau Hotel, Perot State Park, boat launches, bike paths, golfing, Elmaro Vineyard and more!

Top guest favourite
A wooden tray is positioned on a neatly made bed, featuring a bottle of rose wine and two wine glasses. A small vase with a sprig of greenery adds a touch of freshness, complementing the subtle colors of the decorative pillows and bedspread.
Home in Galesville
4.95 out of 5 average rating, 119 reviews

Bright, spacious 3-bedroom farmhouse on 3 acres

Come stay in our recently updated 1800's farmhouse. Situated on 3 acres in a rural setting, this home is the perfect escape while still being centrally located among area attractions. Just 5 miles from the Mississippi, a state park and bike trail, a winery and an orchard, there is an abundance of nearby entertainment throughout the seasons. It is conveniently located between LaCrosse, WI and Winona, MN. WiFi and Roku available. There is ample off-street parking with space for trucks/trailers.

Guest favourite
Home in Dakota
4.81 out of 5 average rating, 27 reviews

River House

Perfect for those seeking tranquility & natural beauty. A peaceful haven offering an ideal setting to relax, recharge, & reconnect while enjoying modern comforts. Start your day with a cup of coffee on the spacious deck as the sun rises over the majestic Mississippi. Breathtaking views make every morning unforgettable. Located just outside Great River Bluffs State Park, miles of scenic hiking / cross country trails that wind through forests & dramatic bluffs view over the Mississippi valley.

Top guest favourite
Farm stay in Bangor
5 out of 5 average rating, 33 reviews

Farm Stay: Show Me the Whey

Cozy, clean, quiet, and comfortable. Located on a fifth-generation, family-owned and operated Wisconsin Dairy Farm. Newly remodeled and nestled in the beautiful driftless region, offering countless recreational opportunities year-round. Just 15 minutes from La Crosse, guests can relax with a warm cup of coffee on the sofa while watching cows wander outside in the pasture. During warmer months, the yard is a perfect place to sit by the fire and listen to the owls call across the valley.

Top guest favourite
A wooden interior is highlighted by a welcoming entrance. A person stands near an open door, removing a jacket, while a dog sits attentively on a textured mat, looking up. Natural light filters in, illuminating the space.
Cabin in Mindoro
4.97 out of 5 average rating, 121 reviews

Stunning Views! - Pettinger @HighPointRetreats

Perched in the solitude of nature, our ridge top cabin offers a picturesque view at one of the top elevations in all La Crosse County. Cozy up to your loved ones, relax with friends, or find inspiration in this luxury cabin in the woods. Pettinger cabin is named after Petting Summit located just east of the cabin. Pettinger sleeps four and is non-smoking. Get your front row sunset seats on the private patio and relax by the fire. Immerse yourself in the tranquility and come stay with us.

Top guest favourite
The expansive home is nestled among a vibrant forest of fall foliage, showcasing a rich palette of oranges, yellows, and greens. Large windows reflect the natural beauty surrounding the property, offering a serene view of the landscape.
Home in Winona
4.97 out of 5 average rating, 201 reviews

Beautiful Views of the Mississippi river

Escape to a private Mississippi River retreat on 18 wooded acres. This spacious 6,300 sq ft home sits up high with stunning views of the river. It sleeps up to 14 with 5 bedrooms, 10 beds, and multiple living areas perfect for groups and gatherings. Enjoy a fully stocked kitchen with two fridges, complimentary coffee, laundry, a game room, games, and an outdoor fire pit. Peaceful, secluded, and designed for comfort—your ideal riverside getaway. No pets. Nearly 200 5-star reviews!!!

Top guest favourite
Cottage in Onalaska
4.9 out of 5 average rating, 405 reviews

Northshore Cottage (2 bedrooms) on Lake Onalaska

Come stay at our cozy and comfortable two bedroom cottage located in a quiet neighborhood with views and access to Lake Onalaska. Walk across the street to hiking/biking trails. Near the Great River State Bike Trail. The Lake Onalaska canoe/kayak trail goes past our shoreline. Two sit on top kayaks and two easy ride bicycles are included. There are fishing boat rentals nearby or you can fish from the shore while enjoying Lake Onalaska's famous sunsets. No cleaning fee!

Top guest favourite
The interior of the silo guesthouse features a circular design with wooden beams overhead. A cozy seating area includes a large sectional sofa and a stylish ottoman. Natural light enters through multiple windows, enhancing the space, while a staircase leads to a loft area.
Farm stay in Caledonia
4.99 out of 5 average rating, 116 reviews

Silo Loft Guesthouse

Our silo guesthouse provides a beautiful country retreat surrounded by hundreds of acres of woods and farm land. This working dairy farm is the perfect stay for a tranquil get away or the full dairy farm experience. If you’re looking for a CLEAN, peaceful & unique stay, this is the place for you! Recent guests say it’s the “hidden gem” of MN! Just 10-30 minutes from local coffee shops, restaurants, and many outdoor activities, this getaway has something for everyone!

Top guest favourite
The lakefront view captures a serene sunset over Lake Onalaska, with reflections of orange and purple hues on the calm water. Grassy reeds along the shoreline frame the scene, offering a peaceful atmosphere amidst the natural beauty of the surroundings.
Flat in Onalaska
4.95 out of 5 average rating, 129 reviews

Waterfront Studio

Waterfront studio The studio is on the edge of the Upper Mississippi Wildlife Refuge. Surrounded on one side by beautiful Lake Onalaska with prairie walking trails on the other. You will not find a closer view of Lake Onalaska. There are two public boat landings less than a mile away. The property is family-owned and operated and has been offered for vacation rentals since the 1960s. Stay and experience all that "God's Country" has to offer. *No cleaning fees*

Top 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, 146 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.

Popular amenities for Richmond holiday rentals

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  4. Winona County
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