Holiday rentals in Cashton

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Top-rated holiday rentals in Cashton

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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, 148 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.

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
4.94 out of 5 average rating, 130 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.

Top guest favourite
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
4.97 out of 5 average rating, 216 reviews

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.

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, 100 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.

Top guest favourite
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
5 out of 5 average rating, 102 reviews

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,

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, 158 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!

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, 134 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!

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, 340 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.

Guest favourite
Home in Westby
4.94 out of 5 average rating, 82 reviews

Secluded 3BDR house great for group gatherings

Beautiful home in the Driftless. 10 minutes outside Viroqua and right above the west fork of the Bad Axe River for the fishermen. This modern former Amish home has a Wolf gas range stove with griddle-top for the chef. Relax on the deck and watch the cattle and sheep graze on the pasture surrounding the house. Well appointed getaway but only 10 minutes to local amenities! A great place to call home base while you're away, we hope you enjoy your stay.

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.
Flat in Westby
5 out of 5 average rating, 20 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.

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.
Guest house in Viroqua
4.98 out of 5 average rating, 216 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).

Top guest favourite
Two wooden Adirondack chairs are positioned on the covered porch, inviting relaxation. A rustic 'WELCOME' sign and a decorative wheel add charm to the warm wooden facade. Natural light filters through the window, enhancing the cozy outdoor space.
Cabin in Ontario
4.99 out of 5 average rating, 113 reviews

Hill Top Hideaway

Opening April 13 2023! Relax and enjoy nature at this peaceful, beautiful hilltop cabin in the driftless region. Close to Billings Creek, KVR and Wildcat Mountain state park. Once a family getaway, this cabin this property has been. updated with modern amenities and including bathroom, updated appliances, sleeping loft and a seperate mini-cabin for the third bedroom space.

Popular amenities for Cashton holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Monroe County
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