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Holiday houses in Glen Haven

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Top-rated holiday rentals in Glen Haven

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

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Guest favourite
A quaint blue house is shown from the side, surrounded by lush green grass. A wooden fence partially outlines the property, with a few flowering plants positioned along the edge. Clear skies and sunlight illuminate the exterior, highlighting its welcoming presence.
Home in Prairie du Chien
4.98 out of 5 average rating, 171 reviews

Ohio Street Retreat- hot tub, massage chair, pool

After a fun day in The Driftless Area, come relax and unwind in Prairie du Chien. Beautifully decorated 2 bedroom home with a spacious kitchen, large island, dishwasher, washer/dryer & 5' walk in shower. We supply all cooking/baking items/utensils. High-speed internet with smart TVs in both bedrooms and living room. Outdoor pool (seasonal), hot tub and massage chair. We love dogs too, so we provide a dog run (there is a pet fee). For our fishermen- there is off street parking for your boats.

Top Guest favourite
A single-story cabin is featured, showcasing a green metal roof and natural wood siding. Large windows allow for ample natural light, while a welcoming front door, framed by a stone chimney, leads to the quiet surroundings of the property.
Cabin in Woodman
5.0 out of 5 average rating, 61 reviews

River Trails Cottage

Have fun with the entire family or a group of friends in a quiet peaceful setting. The cabin sits on 2 acres and attaches to 8700 acres of public land that is open to hunting, hiking and abundant with wildlife which makes this property great for the outdoor enthusiast. The property is 6/10 mile from a public boat landing where you can fish, kayak or canoe the Wisconsin River. There are multiple parks relatively close that offer excellent hiking trails. Direct access to miles of ATV/UTV trails.

Top Guest favourite
Home in Garnavillo
5.0 out of 5 average rating, 36 reviews

River Bluff Retreat-Hot tub & game room

Relax with the whole family at this peaceful retreat just 5 miles from historic Guttenberg, Iowa. Situated on a bluff overlooking the majestic Mississippi River, you'll love the amazing view. This private property offers plenty of space with room for your boats and ATV's. Gather in the large game room, or spread out across multiple living areas. Enjoy the high-speed Starlink internet and complimentary access to YouTube TV and NFL Network. This is the perfect getaway for groups up to 13.

Top Guest favourite
A clear drink adorned with lemon slices and colorful ice cubes rests on a wooden deck railing. In the background, the tranquil waters of the Mississippi River reflect the sky, framed by lush trees and a peaceful shoreline.
Home in Cassville
4.85 out of 5 average rating, 126 reviews

Right on the Mississippi...relax and enjoy!

Our little spot is right on the mighty Mississippi river, a beautiful spot to relax, fish, bird watch including eagles! We feature a large deck facing the water to enjoy morning coffee or an evening cocktail to watch sunsets. When you’re ready to settle in for the evening, we have ready-to-cook kitchen, grill, WiFi, Amazon Prime and Netflix, fireplace and comfy seating. So just relax! Small Wisconsin town with BIG relaxation. See more in this video! https://youtu.be/rM2HnmNMu4U

Top Guest favourite
A lush green landscape rises just beyond a calm river, with a small collection of buildings visible along the shore. The architecture varies, featuring both traditional and modern designs, under a sky filled with fluffy clouds.
Apartment in Clayton
4.94 out of 5 average rating, 174 reviews

Cozy Apartment Steps from the Mighty Mississippi

Disconnect from the daily grind and enjoy a getaway in this welcoming one bedroom apartment, steps away from the Mighty Mississippi. Located in Clayton, Iowa, Located within walking distance of two delicious restaurants and a boat launch., and only 1/2 hour from the Casino Queen, local wineries, Pikes Peak State Park, as well as the historic communities of Elkader, IA and Prairie Du Chien, WI. Need more space? I also offer a two bedroom apartment: www. airbnb. com/rooms/43979345

Top Guest favourite
The log cabin exterior is surrounded by lush greenery and tall grasses. A welcoming porch is highlighted by a wooden rocking chair. Natural light accentuates the cabin's rustic wooden finish, and a roof overhang provides shade to the entryway.
Cabin in Potosi
4.98 out of 5 average rating, 241 reviews

Unplug and get back to nature

The log cabin was built as a place to unwind, relax, and truly unplug. Nestled among 15 acres of rolling hills, the cabin can serve as a place to hunker down and read three novels, or a home base for hiking, cycling and putting the nature back in your life. Be advised, there is NO television and that’s for good reason. Cook, drink, eat, play, relax and refresh yourself. Wake up to the songs of birds and listen to the owls at night while you’re warming yourself around a bonfire.

Superhost
A vibrant orange cabin is set against a backdrop of trees and gentle hills. Large windows and a front door reveal a welcoming appearance. A winding gravel path leads to the entrance, surrounded by lush green landscaping and natural foliage.
Cabin in Bagley
4.89 out of 5 average rating, 233 reviews

**Cozy & Dog Friendly** Rustic Cabin Retreat

Relax and recharge at this country getaway which is tucked amongst trees and the rolling hills. Surround yourself with nature while also having easy in and out access! This makes it a breeze to come and go as you please and explore all southwest Wisconsin has to offer! Ready for the whole family to enjoy, along with their furry friends. *9 minute drive to Wyalusing State Park *10 minute drive to Bagley / Wyalusing Public Beach *16 minute drive to Prairie du Chien

Guest favourite
Tiny home in Guttenberg
4.95 out of 5 average rating, 22 reviews

Suite 1 – Lydia's Loft

This unit is brand new construction for the summer of 2025 featuring a living area with a large projection screen and a fully equipped kitchen with bar and smart TV. The bathroom includes a corner shower and washer/dryer. All sleeping is above in the large open loft with one queen bed, full/twin bunk and twin bed to comfortably sleep up to six. This unit also has an outside dining area/patio. To see the other attached unit, click here: airbnb.com/h/310lincolnslodge

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, 151 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.

Top Guest favourite
An elevated view of the house illustrates a modern structure with a spacious rooftop patio featuring outdoor seating and fire pit. The driveway leads to a garage, surrounded by natural landscaping. Soft lighting emanates from the windows, highlighting the inviting entryway.
Home in Guttenberg
5.0 out of 5 average rating, 29 reviews

Roofscape Retreat

Now renting the entire house! Previously offered as a partial rental, this listing has been updated to include exclusive access to the full home, including all bedrooms, bathrooms, kitchen and outdoor areas. Enjoy 4 bedrooms, 2 living rooms, full kitchen, rooftop patio, garage, and laundry. Steps from parks, pool, fishing, and the Mississippi River. Perfect for families or groups seeking comfort, space, and a central Guttenberg location!

Top Guest favourite
The exterior of a stone cottage is presented, featuring a front porch with a wooden overhang supported by triangular beams. Lush greenery surrounds the entrance, complemented by colorful flower boxes and well-maintained landscaping. The warm tones of the stone create a rustic and inviting appearance.
Cottage in Woodman
5.0 out of 5 average rating, 129 reviews

The Cottage at Streamwalk

Located off the beaten path in a beautiful pristine valley, this 1 bed, 1 ½ bath cottage offers high end furnishings with a vintage flair modeled after a true english stone cottage. The cottage offers miles of private walking trails on 100 private acres along the renowned Big Green trout stream. Our small highland cow herd roams the pastures, making it feel like you truly are in the Scottish Highlands.

Superhost
A brick cottage is set among lush green grass, with a metal roof and partially covered by climbing vines. Decorative plants line the base of the house, and trees surround the property, adding to the natural landscape.
Cottage in Garnavillo
4.69 out of 5 average rating, 154 reviews

Valley Mills Miller's Cottage

Welcome to Valley Mills Miller's Cottage, where the beauty of "Mother Nature" surrounds you. Built six years after Iowa became a state in 1847, it is located in a remote picturesque valley containing Buck Creek Trout Stream. It is completely surrounded by wooded Bluffs, known as "Cold Slopes". With its two acre park like area, it is an ideal place for families to let their Kids/pets freedom to roam.

Popular amenities for Glen Haven holiday rentals