Vacation rentals in Crawford County

4.97 out of 5 average rating, 129 reviews

Cabin in Eastman

TranquiliTree Cabin- Secluded and Relaxing

Are you looking for a cozy, and quiet get-away spot to rest & relax? Our little Tree house Cabin is the perfect spot! Located between Prairie Du Chien, WI and Ferryville, WI- this little A-frame cabin gets you within 5 min. from the river, but allows you to be tucked in a quiet wooded area. It is 900 sq. ft of pure relaxation & nature! Enjoy your morning coffee in the outdoor room or relax nightly by the fire pit. Disconnect 2 Reconnect. TranquiliTree Cabin is a great place to escape and unwind.

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.

4.96 out of 5 average rating, 113 reviews

A cozy cabin is nestled among green trees and vibrant wildflowers, showcasing warm wooden siding and a welcoming porch. The surrounding landscape features a mix of lush foliage, adding to the serene, natural setting of the Driftless area.

Cabin in Boscobel

Cozy creekside Driftless Log Cabin on beaver pond!

Peeping frogs, singing birds, rustling trees, hooting owls, gurgling creek, howling coyotes: these sounds will surround you during a week here! Cabin is cozy, with an aesthetic we're calling (coining?:) supper-club-chic. The perfect place to read, relax, reconnect. Nestled in the heart of Wisconsin's Driftless area, a remote, lovely, nearly-wild kingdom, easy driving distance from Chicago and Madison. 45 minutes to Taliesin, 10 minutes to the Wisconsin River, epic bike rides out the front door.

Apartment in Soldiers Grove

A shaded outdoor area is presented, featuring two picnic tables nestled beneath tall trees. The ground is covered with natural gravel, and dappled sunlight filters through the tree branches. A spacious lawn stretches out in the background, enhancing the outdoor setting.

4.83 out of 5 average rating, 183 reviews

Knotty Pine Rental - Rolling Ground

Knotty Pine Rental is in the heart of all that the Driftless Area has to offer with small town hospitality. Enjoy the days hiking, fishing, visiting local flea/farmers markets, apple orchards, strawberry picking, utv trails, and so much more. We offer free wifi, cable television in the great room, as well as the bed room, small variety of family games, and a deck to enjoy the sunsets. We have a large yard area, lots of parking, and the option to enjoy some taste food at the bar and grill below.

4.8 out of 5 average rating, 420 reviews

A rustic kitchen features wooden beams and a spacious bar counter with seating. The cabin's warm wooden interior includes various appliances and preparation spaces, with natural light filtering in from windows. A separate table area is visible, providing additional seating for dining or activities.

Cabin in Wauzeka

Larsen Rustic Secluded Log Cabin W/Outdoor Hot Tub

Secluded cabin hike the trails to the cave and ponds. Close to trout fishing stream or Mississippi for fishing. Bring you UTV and ride the private trails $25 per driver and 10 per passenger or rent an UTV 300.00 per day Approx 15 miles from Priarie Du Chein, close to canoe outposts for the Kickapoo, Wisconsin river. Has a gas ,charcoal grill,fire pit, pool table, fooseball, ping pong table. Smart TV Private UTV trails are closed Oct 15th thru mid Jan for hunting. Access to public UTV trails.

4.94 out of 5 average rating, 193 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.

4.98 out of 5 average rating, 144 reviews

Cottage in Eastman

Hypoint Loft-Rural SW Wisconsin Mississippi River

Newly Constructed, (2018) Family Owned Loft House in a quiet, relaxing, 2 acre country setting overlooking the Mississippi River! 2500 sq. ft. Just 4 miles from Gatherings on the Ridge, 20 minutes from Historic Downtown Prairie Du Chien and a short jaunt to the river. Sleeps 8-10, master bedroom with a queen, 2 queens & queen sofa sleeper in loft, queen in basement , 2 baths, master bath has jacuzzi tub, full kitchen (pots, pans, dishes, toaster, keurig, coffee pot, coffee, waffle iron, etc.)

4.95 out of 5 average rating, 103 reviews

A spacious deck offers a relaxing outdoor seating area with four chairs and a table, set against the backdrop of the Mississippi River and rolling hills. The sky is filled with clouds, reflecting various shades as the sun sets over the water.

Cabin in Lynxville

River Run Ridge 5 bed/4 bath w/ hot tub & pool!

Come enjoy the breathtaking views all around the living and dining area of this beautiful home located in Lynxville. This upgraded home with 5 bedrooms and 3 baths, can accommodate up to 14 people . Spacious dining/living area for family gatherings, bonus projector room in lower level and large deck to sit and enjoy the view of the Mississippi, be it day or night while grilling out in a summer night. Fully stocked for your getaway. Close proximity to many local attractions and boat ramp.

4.98 out of 5 average rating, 327 reviews

Cabin in Gays Mills

Remote Driftless Gem Stream and Sauna near Viroqua

Settle into this pristine farmhouse nestled in a valley in the rolling, forested hills of the Driftless Region, southwest Wisconsin. Start your day with a cup of local coffee on the front porch. Go on a long walk or bike ride, then return to the cottage to cook, play board games, listen to our record collection or visit Viroqua (25 minute drive) for a farm-to-table 5-star dinner. Build a warm fire outdoors/ warm up by the gas stove indoors, or go down to the stream for a cold plunge/sauna.

4.84 out of 5 average rating, 223 reviews

A refreshing beverage is held up against a scenic backdrop of the Mississippi River. Lush greenery frames the view, with calm waters reflecting the blue sky dotted with clouds. Islands and marshlands can be seen stretching across the horizon, creating a serene landscape.

Home in Lynxville

Highland Hideaway

A cozy, secluded two bedroom cabin located in the driftless region with incredible views of the Mighty Mississippi!!! If your looking for peace, quiet, and beautiful sunsets this is your place. Only 20 minutes from Wyalusing state park, The Effigy Mounds (sacred Indian Burial Grounds) Pikes Peak and Historic Villa Louis. This beautiful cabin centers you 30 miles from amazing hiking, fishing, hunting and nature for a weekend of disconnecting from busy life.

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.

4.82 out of 5 average rating, 187 reviews

The exterior of a log cabin is shown, featuring a warm wooden facade and a peaked roof. A large window allows natural light to enter, while a porch is visible, framed by a rustic wooden beam. Surrounding greenery complements the natural setting.

Cabin in Harpers Ferry

Andy Mountain Cabin #4

Whether you are….. Camping, Gathering with family or friends, Hunting the Yellow River State Forest, Fishing and Boating on the Mississippi River or Snowmobiling ……Andy Mountain Cabins is the perfect Home Base for intimate or large groups. Andy Mountain Cabins, LLC is the prime log cabin choice for lodging or motels in Northeast Iowa, Allamakee County, Harpers Ferry Ia, Prairie du Chien WI, or McGregor Iowa.

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Other great vacation rentals in Crawford County

Apartment in Prairie du Chien

An open layout kitchen and living area is visible, featuring a modern kitchen with white cabinetry and stainless steel appliances. A dining table with red chairs sits beside a cozy couch, accentuated by decorative pillows. Natural light enters through a window dressed with light curtains.

4.97 out of 5 average rating, 66 reviews

4 Seasons Air BnB..Minutes from Every Where!!!

AlanRating, 5 stars4 months ago

we will book again for a long weekend

5 out of 5 average rating, 54 reviews

The open living area features a wooden staircase leading to an upper loft. A spacious dining table sits next to the modern kitchen, complemented by warm wood tones and cozy furnishings. Soft light illuminates from overhead fixtures, creating a welcoming ambiance throughout the space.

Cabin in Ferryville

Aspenshire Cabin: A Nod to English Charm

MaryRating, 5 stars3 weeks ago

We absolutely loved our stay! The cabin is quaint, private, and incredibly peaceful. Everything was spotless—the place was extremely clean and clearly well cared for. The cozy, beautifully curated decor made it feel like a true retreat. Highly recommend for anyone looking to relax and unwind in comfort!

5 out of 5 average rating, 70 reviews

A fire pit made of rusted metal is surrounded by five green plastic chairs on a grassy area. The setting is framed by trees and foliage, creating a comfortable outdoor gathering space.

Home in Soldiers Grove

Rock's Rental House

NicoleRating, 5 stars1 month ago

Beautiful area to spend time with family.

4.95 out of 5 average rating, 41 reviews

The red A-frame cabin is nestled among dense green trees, featuring a welcoming covered front porch with railing. A picnic table is situated nearby, surrounded by lush foliage. Sunlight filters through the leaves, enhancing the peaceful woodland setting.

Cottage in Ferryville

Mississippi River Getaway – Spirit Mound Cottage

JoeyRating, 5 stars7 months ago

We just finished up a stay at Jans cabin, for 5 days of duck hunting. the place was as described, very comfortable, and the beds slept well after long days on the water. We will definitely be booking again for the next duck hunting trip.

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 stars1 week 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, 13 reviews

Home in Eastman

Lookout Lodge Mississippi River retreat

AdamRating, 5 stars2 weeks ago

The property was incredible. The layout is great with plenty of room for lots of people to enjoy the beautiful panoramic sunsets that seem to last for hours. The facility has great updated amenities, but manages to keep its rustic feel at the same time. We'll definitely be back.

5 out of 5 average rating, 14 reviews

The open-concept living, dining, and kitchen area is showcased with wooden accents and abundant natural light. A large sofa faces a rustic coffee table, while the kitchen features modern appliances and ample seating at the island. Windows provide views of the surrounding landscape.

Cabin in Soldiers Grove

Ridgetop Driftless Cabin 2

MelindaRating, 5 stars2 weeks ago

This was our second time staying at this adorable cabin. When we first arrived, the electricity flickered off and on; in the morning we had no water. I started texting Jodi the night before and in the morning. She was quick to secure an electrician who had everything running by late afternoon. All was handled quickly and efficiently. We also met Jodi’s, her husband and brother-in-law. We feel like good friends