Vacation rentals in Saint Olaf

5 out of 5 average rating, 106 reviews

A flock of chickens, including various breeds, roams freely in a grassy area bordered by a wire fence. Lush greenery and trees create a natural backdrop, enhancing the pastoral setting.

Farm stay in Decorah

Footbridge Farm Cabin

Footbridge Farm is a quiet country get-away located on 90 wooded acres, 15 miles NE of Decorah. We are close to the mouth of Canoe Creek, the Upper Iowa River and adjacent to state DNR land. The cozy owner-built cabin has an open ceiling with exposed beams and rafters giving a sense of spaciousness. Local stone was used in the exterior walls and the floor-to-ceiling fire back behind the wood-burning stove. The floors are oak and slate. Detailed craftsmanship can be found throughout the cabin.

4.96 out of 5 average rating, 289 reviews

A charming outdoor courtyard features a small table and two chairs positioned beside a brick fireplace, set against a natural rock wall. Decorative items are displayed on the mantel, while greenery adds a touch of nature to the space.

Apartment in McGregor

Cave Courtyard Guest Studio

The Cave Courtyard Guest Studio. A relaxing getaway located on the ground floor of an 1848 historic building just 1 block from the Mississippi River and unique shops and eateries. Sleeps 4 with a queen bed and daybed with pull out trundle, private entrance, private bath with shower, kitchenette with microwave and mini fridge, internet, cable tv and air-conditioning. There is also a private courtyard located below unique cliff side caves. Some food items are also supplied. Adults only-no pets.

4.94 out of 5 average rating, 194 reviews

The Victorian home features a charming architectural design with a turret and expansive wrap-around porch. Large windows are adorned with decorative trim and flower boxes, surrounded by neatly landscaped gardens and lush greenery.

Home in McGregor

McGregor Manor Victorian Getaway

Welcome to our beautiful Victorian home located in the quaint town of McGregor, Iowa. Our 2,800 sq. ft. home was built during McGregor's early years as a Mississippi River boom town. Attractions include antiquing, biking, fishing, hunting, hiking and boating! We're a short drive from Pike's Peak, Effigy Mounds and Prairie du Chien. All four bedrooms include a private bath, providing comfort and privacy for each member of your group. Fully furnished and decorated. See below for more details.

4.92 out of 5 average rating, 108 reviews

A fire pit is surrounded by a low stone wall and black metal chairs. Flames dance from the center of the pit, providing warmth. The historic brick courthouse is visible across the street, featuring multiple arched windows and a prominent entrance.

Guest suite in Elkader

The Bridge View Studio

Perfect getaway and a perfect location to get to know Elkader with it’s coffee shops, antique mall, shops, opera house and beautiful Turkey River. Property was homesteaded in 1841 and sits directly across from the courthouse and looks over the famous Keystone Bridge and downtown. Come stay awhile. ***NOTE: Because we are located across from the court house the clock tower bells can be heard from our location. Main part of the house is our residence, Airb&b has separate entrance on the side.

4.95 out of 5 average rating, 182 reviews

Tiny home in Monona

Creekside-water and nature lovers paradise

Is this Heaven? Maybe. Are you looking for a fun getaway for yourself, family, or friends? Well, look no further. Our place is ready for you to make lifelong memories. Create and tell stories while sitting under the stars next to the crackling campfire. Do your morning yoga by the babbling stream. Hike the trails. Soak up the sun on the sandy beach while listening to the waterfall. Laugh and splash your kiddos in our pond. Beach chairs, sand toys, floaties, kayaks, and more.

4.93 out of 5 average rating, 140 reviews

The image showcases a scenic view of a quaint riverside street. Beautiful fluffy clouds fill the blue sky above, while a mix of parked vehicles line the road. The Mighty Mississippi is visible in the background, bordered by lush green hills.

Apartment in Clayton

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

4.89 out of 5 average rating, 192 reviews

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

**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

4.8 out of 5 average rating, 122 reviews

A fire pit surrounded by green adirondack chairs is positioned on a gravel area, with a view of the Mississippi River in the background. Large trees provide shaded spots, and additional seating is visible near the water.

Tiny home in McGregor

The Cottage

A Quaint Cottage on the Mississippi River one mile north of Marquette, IA. One bedroom with additional sofa sleeper in the common area. Public boat landing, Casino and Winery all within one mile. Gas grill and fire pit on site. Effigy Mounds and Pikes Peak within 3 miles. Prairie du Chien just across the bridge. Great eating and shopping in nearby McGregor! Fun family getaway or great area for fishermen! Seasonal cottage books May thru Mid October.

4.99 out of 5 average rating, 278 reviews

A person stands in a gentle stream, casting a fishing line into the water. Sunlight filters through the surrounding trees, creating a shimmering effect on the water's surface. The lush greenery along the banks adds to the natural setting.

Apartment in Decorah

Berry Hill Flat

Berry Hill Flat sits perched on a bluff above Trout River Valley. Trout live in beautiful places and so do we! The Flat offers a king bed in the bedroom, full bathroom, full kitchen, living room, twin bed, and private ground floor entrance. It is the lower level of our beautiful log home nestled in the walnut trees. Minutes to Decorah, Waukon, or the trout stream in the Valley below.

4.98 out of 5 average rating, 294 reviews

A spacious outdoor deck is shown, featuring a wooden picnic table and a set of metal chairs around a circular table. Natural greenery surrounds the area, providing a peaceful setting. The deck's wooden flooring complements the rustic charm of the surroundings.

Cabin in Harpers Ferry

Yellow River Getaway

2 Bedroom cabin with Queen Beds and Queen Sofa sleeper with comfortable mattress if you want to pitch a tent in the yard feel free. Large open living area. with firepit. 170 acres of private property with cell phone service. Nestled in the country on a dead end road. One mile from trout fishing, hunting, hiking, horseback riding and 8500 acres of Yellow River State Forest.

4.97 out of 5 average rating, 113 reviews

Home in Monona

Driftless Manor Getaway

The Driftless Manor Getaway is a perfect location for you and your friends or family to stay! The Driftless area has many activites such as antiquing, biking, boating, fishing, gambling, hiking, hunting, shopping, and winery/brewery hopping! Come explore the area to see what adventures you can find while staying in a roomy, relaxing space!

Bungalow in Prairie du Chien

A welcoming entrance reveals a cozy living area with hardwood floors and natural light. The door opens to a spacious seating area featuring a sofa and a coffee table, while a blue chair adds a pop of color. A rug defines the entryway space.

4.94 out of 5 average rating, 109 reviews

Prairie Street Bungalow steps from Blackhawk Ave

Experience the century old charm of our refinished bungalow and soak in all the outdoor opportunities of the Driftless Region. The Prairie Street Bungalow is located steps from the mighty Mississippi and just two blocks from the historic Blackhawk Avenue.

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Other great vacation rentals in Saint Olaf

5 out of 5 average rating, 22 reviews

A fire pit is seen surrounded by rocks, with flames dancing above logs. In the background, the calm Wisconsin River reflects the colors of the sunset, framed by lush greenery and trees. A peaceful setting invites relaxation and gathering outdoors.

Cabin in Woodman

River Trails Cottage

TeresaRating, 5 stars1 month ago

Amazing cabin stay! Beautiful and serene setting. Kirk was very accommodating and very fast at answering any questions.

Cabin in Prairie du Chien

A serene outdoor setting features two black adirondack chairs positioned on a pebbled area by the water's edge. A fire pit is visible, and a private pier extends into the tranquil river, surrounded by lush greenery and distant hills under a clear blue sky.

5 out of 5 average rating, 18 reviews

Prairiedise Riverside Retreat!

AlexandraRating, 5 stars2 weeks ago

We loved our stay! The deck with an amazing view was spectacular and the house has everything we needed.

5 out of 5 average rating, 16 reviews

A view from the spacious deck captures the Mississippi River with a tugboat navigating the waters. Green trees line the opposite shore under a clear blue sky, offering a scenic backdrop for relaxation.

Apartment in Guttenberg

August & Alma’s

GertRating, 5 stars2 weeks ago

Just like during my first visit, Cindy’s house was perfect with a location on the river that is stunning and easy walks to shops and restaurants. This time ‘round my wife was with me and she loved the house, too. It was very comfortable, quiet and well equipped with everything we needed. We highly recommend Cindy’s place.

5 out of 5 average rating, 6 reviews

Cabin in De Soto

Hygge Cabin, Sauna-Firepit-BBQ

JohnRating, 5 stars2 weeks ago

Clean, newly updated, everything we needed available, easy to find, great communication and quick response from owner, everything worked perfectly, peaceful private location , and well priced, what more can you asked for. I’m already planning my next fishing trip and plan on staying here again.

5 out of 5 average rating, 59 reviews

A charming tiny house with a wooden façade and a metal roof is surrounded by well-maintained gardens. A green lawn is visible, with a small dog standing near the flower beds. Several windows provide natural light against a clear blue sky.

Tiny home in Fayette

Chicken Coop Tiny House

SharleenRating, 5 stars1 month ago

I stayed for a week and it was great. I will definitely stay here again.

4.8 out of 5 average rating, 71 reviews

A spacious living area features a large sectional sofa with an attached ottoman, positioned beside a stone wall. Large glass doors open to a balcony, allowing natural light to brighten the room. A round clock and speakers are mounted on the wall, adding functional elements.

Apartment in Guttenberg

Mr. Rogers River View

MaryRating, 5 stars1 month ago

Nicely-redone unit. Clean 1 bed up 1 down. Great view from the deck.Easy access to food and drinks. Fishing across the street. I liked it a lot, good value

4.83 out of 5 average rating, 23 reviews

The image shows a wooden staircase leading down from a covered porch, framed by railings. A pathway is visible at the bottom, covered with grass, and a grassy area extends beyond. A small shelter with a blue roof stands in the distance.

Home in Elkader

Small-town Charmer (please read all details)

CraigRating, 5 stars3 weeks ago

an amazing place to sleep, we really didn't eat there but had a nice kitchen, bedrooms, and living area. will be back soon, I would recommend it to family and friends if they want to stay somewhere close to elkader.