Vacation rentals in Westby

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Top-rated vacation rentals in Westby

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Top guest favorite

An arcade room features a foosball table at its center, surrounded by various arcade games and a dartboard. Natural light streams through a large window, illuminating the rustic wooden walls and ceiling, creating a welcoming space for entertainment.

Cabin in Coon Valley

Valley Lodge w/Hot Tub & Arcade

Get your game on at this fun & fashionable lodge in the valley. Come relax in the hot tub, sip coffee by the fire or challenge someone in the arcade. The Cattle Valley Lodge has something to offer every family member. 2 spacious bedrooms with a king bed & 2 queens. Sofa pull out bed, air mattress & cots for extra sleeping areas. Open kitchen/dining/living room provides an awesome space to entertain your family & friends. Large dining table & unique pub style barrel table w/tractor seat stools.

4.97 out of 5 average rating, 224 reviews

Top guest favorite

A modern shipping container home is situated on a grassy hillside, featuring a deck with outdoor seating and a grill. Large windows reflect the surrounding greenery. The building's sleek, black exterior contrasts with the blue sky and clouds overhead.

Shipping container in Westby

Hidden Hillside Getaway

Enjoy a secluded stay in a peaceful country setting. Our modern shipping container home is nestled on a hillside in the corner of our 160 acre farm where you can hike, or snowshoe. This unique space has 2 bedrooms on opposite sides of the house, making it perfect for two couples, The property is a 5 min drive from Viroqua and Westby, WI. The Driftless area has a variety of year-round outdoors activities including trout fishing, hiking, biking, canoeing, snowshoeing, and sledding,

5.0 out of 5 average rating, 112 reviews

Top guest favorite

A modern kitchen area features white cabinetry and stainless steel appliances, including a gas stove and microwave. A cozy living space includes a sofa with colorful throw pillows, while a loft area is visible above, providing additional sleeping space. Natural wood floors create a warm ambiance.

Guest suite in Viroqua

Maple Ridge Guest Apartment

This apartment was added to the back of our detached garage about 10 years ago. Low or no VOC products were used throughout construction. Brand new appliances installed with an oven big enough to cook the biggest turkey I’ve ever dreamed of. Spectacular ridge top views and beautiful starry nights. Hiking and cross country ski trails on the property of about 75 acres. Pick hazelnuts in the fall, collect and boil your own maple sap in the spring and pick blueberries in the summer.

4.98 out of 5 average rating, 165 reviews

Top guest favorite

The ranch-style home is showcased with a spacious driveway, featuring a two-car garage. Lush greenery surrounds the property, and the clear blue sky adds brightness to the scene. The exterior is comprised of colorful siding and well-maintained landscaping.

Home in Cashton

Cashton Eagle Retreat

UPDATE: Enjoy your stay with HIGH-SPEED internet! Located just outside of the small town of Cashton, WI, this newer built ranch style home is right in the heart of Amish country. The house has two bedrooms, two bathrooms, an open concept dining/living room, large yard for activities and a usable two-car garage. ATV friendly roads, snowmobiling trails, and public hunting & fishing are all nearby. Enjoy the simple life in the country as long as you wish. Everyone is welcome!

5.0 out of 5 average rating, 138 reviews

Top guest favorite

A modern living area features a dark sofa complemented by a vibrant orange chair. A decorative area rug with blue and orange patterns adds warmth. Natural light filters through three windows, illuminating the stylish decor and shelving on the wall.

Apartment in Viroqua

Bright two bedroom rental in the heart of downtown

Enjoy a comfortable experience at this centrally-located rental, just steps away from downtown Viroqua. Grab a coffee at Wonderstate Cafe before heading over to the farmers market right next door. Explore the thriving art scene and local shops, before finishing off the evening with a dinner at the Driftless Cafe. This will also make a great homebase for hiking, biking, fishing, and paddling out in the great Driftless area. We love our little town, and hope you do too!

4.94 out of 5 average rating, 203 reviews

Top guest favorite

A spacious sleeping area features a large bed covered with a soft gray quilt. A small dining table is set near a window, surrounded by light curtains that allow natural light. A bookshelf and decorative plants enhance the inviting ambiance.

Apartment in Viroqua

Viroqua Studio With a Backyard View

Formerly Del Sol Chocolate factory, the space is in a quiet, residential area close to Eckhart Park and within walking distance to all of the great spots. Apartment is an addition off of the back of my house, with views into the backyard, and with a private entrance. The apartment features a full bathroom with a shower, and also a kitchenette. (small frig., toaster oven, french press). Wifi is available, and also internet access with ethernet is. Fragrance free.

4.94 out of 5 average rating, 240 reviews

Top guest favorite

A serene view of a two-story cottage situated next to a reflective creek, surrounded by lush greenery. The building features large windows that offer a glimpse into the inviting interior. The clear blue sky and sun-dappled trees enhance the peaceful atmosphere.

Cottage in Westby

Timber Creek Retreat

Timber Coulee Creek, a Class 1 trout stream, ripples right through the backyard. King size bed, roomy heated garage for your car. You will enjoy watching deer and turkey as they amble through the property. Bald eagles soar overhead and fish jump in the stream. Listen to the gurgle of the water flowing over the rocks and the music of the birds. Try your hand at fly fishing. Sit around the fire pit, roast marshmallows, watch the flames dance and the stars come out.

4.99 out of 5 average rating, 166 reviews

Top guest favorite

The kitchen features wooden cabinetry with a natural finish, offering ample storage. A large countertop accommodates seating options. Modern appliances are included, such as a black gas stove and microwave. The layout presents an inviting space for meal preparation and dining.

Apartment in Viroqua

Polyshades of Gray

Park once and enjoy Viroqua on foot. This first-floor, one-bedroom stay is across from City Hall and within an easy walk of local restaurants, coffee shops, galleries, parks and the Saturday farmers market. It sleeps up to four with a queen bedroom and sofa bed, plus a full kitchen, fast Wi-Fi, dedicated workspace, smart-lock entry and free parking. It is a comfortable home base for couples, solo travelers, remote workers and people visiting family.

4.92 out of 5 average rating, 132 reviews

Guest favorite

A bright and modern kitchen features white cabinetry and marble countertops. A wooden island with two white chairs is centrally positioned, providing additional workspace. Natural light fills the room through a nearby window, highlighting the stainless-steel appliances and organized kitchenware.

Apartment in Viroqua

Bright airy 2 bedroom apartment - Yellow Door

Second floor apartment remodeled in 2019, wood floors, ceiling fans in every room. Great light with country feel right in Viroqua. Private outdoor entrance with deck. Keyless entry. Fully stocked kitchen. This is a wonderful place to get away and is available for longer stays. Pets are allowed but we do like to know about them. Wood floors do squeak but noise does not transfer downstairs as we have double insulated between apartments.

4.94 out of 5 average rating, 236 reviews

Top guest favorite

A traditional farmhouse is featured, set against a backdrop of green fields. The white exterior is complemented by a green metal roof. A spacious deck with seating is visible, surrounded by lush grass and landscaped gardens, with a decorative white picket fence in the foreground.

Farm stay in Viroqua

The Home Place

Welcome to the Home Place, a fourth generation farm. The Home Place was a working dairy farm up until the winter of 2018, and the Oldenburg's still plant over 270 acres of corn, soybeans, oats and alfalfa. All four generations of the Oldenburg's refer to the farmhouse as "The Home Place". This homey farmhouse is located in rural Wisconsin, and embodies the essence of a traditional farmhouse with modern updates.

4.98 out of 5 average rating, 105 reviews

Top guest favorite

An overhead view displays a spacious living area with a light wood dining table surrounded by four chairs. A comfortable gray sofa, accented with cushions, faces a wood stove. Natural light floods the room, highlighting the warm wood beams and various indoor plants.

Guesthouse in Viroqua

stylish guesthouse minutes from viroqua

Experience for yourself everything the Driftless has to offer during your stay in this stylish, timber-framed, eco-friendly guesthouse on our 8-acre rural retreat. Completed in 2021, you'll love this bright, clean, private, and peaceful space. Fish nearby trout streams, go for a bike ride, explore great state and county parks, or shop and dine in Viroqua (7 miles away) and Westby (3 miles).

4.98 out of 5 average rating, 224 reviews

Top guest favorite

The exterior of a modern wooden home is set against a backdrop of lush greenery. A stone pathway leads to a series of large glass doors, framed by a covered porch. A fire pit is positioned on a grassy lawn, with wooden loungers nearby, inviting relaxation.

Home in La Farge

Amazing Views at this Cozy Retreat

This is your place to relax with the whole family in the Driftless. With south facing views of the Kickapoo River valley, this sunlit and energy efficient home is a perfect retreat. You may hear sandhill cranes, Canadian geese, white swans, spring peepers, and maybe even coyotes howling in the distance at dusk.

4.98 out of 5 average rating, 188 reviews