Holiday houses in Cashton

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Top-rated holiday rentals in Cashton

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

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Top Guest favourite

A cozy cabin is situated among lush greenery, featuring a spacious deck that extends from the entrance. The gravel driveway leads up to the cabin, surrounded by trees and wild foliage, creating a serene, natural atmosphere.

Cabin in Westby

4.99 out of 5 average rating, 152 reviews

Nature’s Nest

Unwind and immerse yourself in nature at this cozy cabin overlooking Timber Coulee Creek. Large living room windows and a spacious deck provide you with a bird’s eye view of the rippling river and many types of wild life. Deer amble through the property; eagles soar and keep an eagle eye on everything. Turkeys, squirrels, coons, and myriad of birds go about their business in this serene environment. Trout fishing is an excellent pastime for those who care to cast a line. Rest, at Nature’s Nest.

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Top Guest favourite

A rustic log cabin is framed by green trees, featuring a steeply pitched roof and decorative wood accents. A welcoming front porch leads to a door with a unique design, while a large window showcases flowing red curtains, blending natural elements with cabin charm.

Cabin in Ontario

4.92 out of 5 average rating, 132 reviews

Country Living Cabin

Brush Creek Log Cabins is your perfect get away for couples or the whole family. If you are looking to relax, do some recreational activities like canoeing , bike riding, hiking, antiquing and Amish shopping or spend time with that special someone you can find it just a few hours from home. We are in between Ontario and Cashton, off of Hwy 33. Over looking the Amish farms below. There are fairs and festivals many with tractor pulls nearby. Warrens cranberry festival and the Dells are nearby.

LocationFamilyNearby

Top Guest favourite

A charming cabin exterior is framed by lush greenery and vibrant white hydrangea blooms. The entrance features a screened door topped by a striped awning. The cabin's black siding contrasts with the surrounding landscape and is enhanced by a picturesque sky filled with clouds.

Cabin in Cashton

4.97 out of 5 average rating, 97 reviews

Outsider's Rustic Retreat

Take it easy at this unique and tranquil getaway. Enjoy the privacy and quiet allure of the Driftless Region. The cabin is located 250 yards from a Class "A" trout stream and includes access to miles of biking roads as well as nearby kayaking opportunities! You also have access to the upper loft of the barn located just a stones throw away. The barn loft includes an honesty bar, pool and darts. I also accept campers/tents ($25/night). Pets are required to be kenneled if left unattended.

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Top Guest favourite

The kitchen features custom Amish shaker style cabinets with walnut butcher block countertops and a mobile accent island with four barstools. Stainless steel appliances, including a gas range, blend with the rustic decor, while natural light streams in through large windows.

Cabin in Cashton

4.95 out of 5 average rating, 101 reviews

Rocky Ridge Retreat - A modern rustic cabin.

Rocky Ridge Retreat is located in the heart of Wisconsin’s Driftless area in a beautiful valley between Cashton and Coon Valley. Our 665 square foot modern rustic cabin comfortably sleeps five and is truly a fly fisher’s paradise sitting on 10 hillside acres with a tributary of Rullands Coulee Creek across the road. Public access to Rullands Coulee and Timber Coulee Creeks are only a few miles away. We are licensed to operate a Short-term Rental by the State of Wisconsin DATCP.

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Top Guest favourite

A view is captured from the entrance toward a bright open dining area, featuring a wooden table surrounded by chairs. An updated kitchen area displays modern appliances, including a coffee maker, with wood cabinetry and a countertop visible beside a framed window that invites natural light.

Home in La Farge

4.97 out of 5 average rating, 160 reviews

The Nestled Inn -King bed, soaker tub, 2 bathrooms

All new kitchen appliances. 1700 sq ft living area. Open floor plan with sunroom. Large bathroom with walk-in tile shower, additional bathroom with soaker tub. Enjoy the outdoor open deck area perfect for family dining. Comes equipped with a gas grill and plenty of seating. Cozy screen-in deck area. Enjoy spacious backyard. Enter home through the large attached garage. This home is set in the country near working farms and a small Amish community. New central air system!

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Top Guest favourite

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

5 out of 5 average rating, 135 reviews

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!

ValueLocationAccess

Top Guest favourite

An aerial view captures the expansive farmland with a cluster of cabins among lush greenery. The setting sun casts a warm glow over the landscape, which features a mix of fields, trees, and a winding road. Structures on the property are visible, blending with the natural surroundings.

Farm stay in Sparta

4.94 out of 5 average rating, 342 reviews

Grapevine Log Cabins

Grapevine Log Cabins, based in Sparta WI, offers pet friendly cabin rentals on a family dairy farm. Amenities and activities include: a walking trail, bike trail, cows in pasture, indoor and outdoor fireplaces, grills outside (there is no cooking in the cabins), Air Conditioning, Heat and firewood is supplied. Nearby activities include: canoeing, fishing, 4 wheeling, antiquing, and superb scenic sites. Pet Policy: Pets may stay with you for an extra $25 per pet/night.

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Top Guest favourite

An outdoor deck features a cedar hot tub and seating area, surrounded by natural landscapes. In the background, a fire pit is set up with chairs, while a picturesque sunset casts a warm glow over the serene surroundings.

Cabin in Viola

4.99 out of 5 average rating, 174 reviews

Secluded cabin,cedar sauna & hot tub,outdoorshower

360 views in the middle of 75 organic acres, no neighbors in site. Outdoor Cedar hot tub & infrared sauna, heated outdoor shower, two king loft bedrooms, full kitchen, back deck with custom hibachi grill to watch sunrise and front covered deck to watch sunset. Indoor/ outdoor fire places. Wildflower fields.We try to give our couples priority booking when they rent our wedding venue 2 miles down the hill (Chapters on the Horizon) that is why we do not instant book.

ValueFamilyComfort

Top Guest favourite

The cabin exterior exhibits a rustic wooden facade, complemented by multiple windows allowing natural light. A stone pathway leads to a covered seating area surrounded by colorful flower beds, providing a serene view of the lush landscape.

Cabin in Ontario

4.97 out of 5 average rating, 88 reviews

Brush Creek Hideaway

Take a break and unwind at this peaceful oasis. Located on the former Brushcreek campground the cabin overlooks pond Bring your fishing pole and enjoy catch and release fishing or just relax on the covered porch and enjoy the sights and sounds of nature. Explore the driftless region of Wisconsin wether it’s hiking, biking, kayaking shopping at the Amish shops or checkout our areas other unique shops and eateries our area offers something for everyone

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Top Guest favourite

The spacious living area features wooden beams across the ceiling, enhancing the vintage design. A cozy seating area includes a brown sofa facing a fireplace, with a flat-screen TV above it. Natural light floods in from the windows, creating a warm and welcoming ambiance.

Apartment in Westby

5 out of 5 average rating, 22 reviews

Newry General - Vintage Flat

This inviting flat, nestled in the northeastern part of Westby, WI, in the charming community of Newry. With 1,000 square feet of living space, it offers a comfortable retreat that honors its historical significance. Modern amenities seamlessly blend with the vintage ambiance, ensuring a restful stay rich in character. Whether you’re here for a brief visit or an extended stay, comfort and nostalgia await you.

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Top Guest favourite

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

4.98 out of 5 average rating, 220 reviews

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).

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Guest favourite

Barn in Westby

5 out of 5 average rating, 11 reviews

Reclaimed barndo retreat- peaceful country escape.

Unique barndominium retreat for couples seeking a peaceful get away. Sitting on a scenic and private 50 acre acre farm with stunning views of a small slice of the driftless area. Charming and stylish space featuring re-claimed barnwood furniture and kitchen cabinets. Sorry, no pets or kids, this space is designed for a relaxing and romantic environment.

LocationDecorGetting around