Guesthouse holiday rentals in Wisconsin

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Top-rated Guesthouses in Wisconsin

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Guest favourite
A serene lakeshore scene is captured at sunset, with the sun dipping below the horizon, casting warm hues across the sky. Gentle waves are visible in the foreground, while smooth stones line the water's edge.
Guesthouse in Oostburg
4.91 out of 5 average rating, 374 reviews

Beach House

This guesthouse is detached from the main house, comes with garage parking and has all the amenities you need including a wood-burning fire place! Towels, bath tissue, soaps & travel items. AC Window Unit. Kitchen includes pots/pans, dishes, mugs/glasses, coffee pot, toaster & microwave. Paper goods. New appliances/new water heater in 2020. Stairs to the apartment are on the northeast corner of the garage. The beach is steps away with a fire pit, boat house lounge, kayaks, beach toys & bicycles.

Top Guest favourite
A rustic cabin with a wooden structure is surrounded by lush greenery. A small porch features a woven chair, inviting relaxation while enjoying nature. The roof slopes gently over the entrance, and a wooden railing provides a charming, natural setting.
Guesthouse in Ontario
4.96 out of 5 average rating, 322 reviews

Rustic Spring Cabin at Echo Valley Farm

Next to a spring and gardens. Glamping with electricity, wood burning stove and supplied water. Charcoal grill and fire pit available. Parking at the cabin. Non chemical port-o-let toilet is a short walk. 3 miles from Wildcat Mountain State Park and 7 miles from the Kickapoo Valley Reserve. Great for hiking and immersing in Nature. This cabin is located near another farm resident's cabin. Bakery's open on Saturdays May - October or order in advance in off season. LGBTQ owned. BIPOC welcomed.

Top Guest favourite
A serene sleeping area features a queen bed with a green quilt and decorative pillows. Flanking lamps provide soft lighting next to the bed. A forest-themed wall mural enhances the calming atmosphere, while a window offers a glimpse of the outdoors.
Guesthouse in Sayner
4.97 out of 5 average rating, 217 reviews

Hike & Hot Sauna at the Loft-Lands End at the Edge

November: Tamarack Time & QUIET time! PRIVATE zenny retreat, rustic SAUNA & upper screened-in deck above NHAL wilderness-A cozy escape! Even rainy days, you'll find peace on the covered deck, listening to raindrops on a tin roof. Howling wolves, a floodlight to gaze out into the forest. Gas grill, firetable, rustic SAUNA. WIFI, elect FP, kitch, full fridge. LostCanoe Lk, WhiteSand Lk, Escanaba & Lumberjack St Trls in 5min. Paved HeartofVilas Trl 10min. Semi-secluded yet 8mi to BJ restaurants!!

Guest favourite
A serene view of the Wisconsin River is framed by two trees adorned with planters. A birdhouse is visible, surrounded by colorful flowerbeds that enhance the natural beauty of the waterfront landscape.
Guesthouse in Wisconsin Dells
4.85 out of 5 average rating, 343 reviews

Waterfront Cottage with beautiful views

This waterfront cottage has beautiful views of the Wisconsin River. My husband and I have lived here for more than 20 years. We love this area - there is nothing like a cool, crisp Midwest morning overlooking the Wisconsin River. Or enjoying a great glass of wine (or Wisconsin beer) while watching a spectacular summer sunset from the deck. Expect peace and tranquility as we are far enough from Downtown Dells to avoid the crowds and noise. We look forward to hosting you and your loved ones.

Top Guest favourite
The exterior of a rustic studio retreat showcases wooden siding illuminated by warm lights at dusk. Large windows offer glimpses of the cozy interior, while kayaks are hung on the side. Surrounding greenery creates a natural ambiance, with a gravel path leading to the entrance.
Guesthouse in Mount Horeb
4.96 out of 5 average rating, 629 reviews

Cool, Roomy, Scenic Country Art Studio

Creative souls love my marvelous studio retreat, a delightful one-room loft-style space featuring tall ceilings, an entire wall of sliding glass doors, kitchenette, piano, and an expansive view of a picturesque barn, pasture, and wooded hills. This amazing, heated, spacious country getaway has no plumbing— it's just a few steps across the yard to the main house guest bathroom. Come create, relax, and renew here! Well-behaved dogs, included in your reservation, must be leashed when outside.

Top Guest favourite
A charming red cottage is nestled among tall trees, showcasing a welcoming front with two white Adirondack chairs placed on a natural surface. Decorative flower arrangements hang near the entrance, surrounded by lush greenery and plants.
Guesthouse in Ashland
4.99 out of 5 average rating, 392 reviews

Norrsken Scandinavian Cottage

The guest cottage is painted to resemble a Scandinavian retreat. Complete with separate bedroom, extra fold-out sofa queen bed, kitchenette, wood burning stove, WiFi (the best we can find but not great!!!) and large television (DirecTV), it is a great getaway for a couple or a family. Owners live on property if you need anything. If you are a bit adventurous, we can put up a tent right next to Lake Superior. The entire property is smoke free. For a quiet stay, no snowmobiles or ATVs.

Guest favourite
A charming cottage is framed by lush greenery, with a stone pathway leading to the welcoming front porch. The exterior features light yellow siding and white trim, complemented by a vibrant blue door. Surrounding foliage adds to the secluded atmosphere.
Guesthouse in Mineral Point
4.94 out of 5 average rating, 286 reviews

Lumber Yard Cottage, a cozy retreat

The Lumber Yard Cottage is a cozy hidden retreat tucked away from the road. Within walking distance of all Mineral Point has to offer. Great restaurants on all sides of this property and wonderful shops are just up the road. The Cheese Trail and railroad museum are across the street. Enjoy the back porch with the wraparound stone wall or the lovely front porch and watch the world slowly drift by. There is a queen size bed, jacuzzi tub, gas fireplace, ac unit, full kitchenette, and wi-fi.

Top Guest favourite
A quaint cottage stands surrounded by snow-covered trees, with a light grey door and window accents visible. The structure features a simple white exterior, complemented by a winter landscape of freshly fallen snow, creating a serene and peaceful atmosphere.
Guesthouse in Fish Creek
4.96 out of 5 average rating, 254 reviews

Vintage Mod Cottage with fireplace & soaking tub!

Grandview Farm Cottage is a circa 1920s newly renovated, 420 sq. ft. private guesthouse on the grounds of a 2.5 acre Door County property built in the late 1800s. Modern, industrial and repurposed style meets vintage farmhouse charm. Central location allows for quick drive or even a bike ride to either coast of the peninsula. Enjoy nature, wildlife, your own organically grown gardens, and dark starry night skies, while being only 3 miles to nightlife and shopping and beaches and parks.

Top Guest favourite
A cozy living area features a white-bricked fireplace with an arch-shaped mirror above it. A round table with two chairs stands adjacent to the fireplace, while a light blue chair is positioned nearby. Soft natural light enters through the window, enhancing the serene atmosphere.
Guesthouse in Sun Prairie
4.98 out of 5 average rating, 374 reviews

Charming Milkhouse Cottage, minutes from Madison!

Welcome to The Milkhouse Cottage! Serving as an original milkhouse from the late 1800s on our pre-civil war farmhouse property, you will feel the timeless elegance of the original character and the beautiful french cottage decor. Perfect for couples, travelers, or business persons -- come and unwind in the scenic heartland countryside and rustic elegance, all with the convenience of location -- we are a quick 15 minute drive from the airport and all that Madison has to offer!

Guest favourite
The spacious living area is characterized by high wooden ceilings and an open layout. Comfortable seating options include a sofa and armchairs, with a coffee table in the center. A large TV is positioned against one wall, while a dining area and kitchen are visible in the background.
Guesthouse in Spooner
4.95 out of 5 average rating, 103 reviews

Secluded Northwoods Cabin

Beautiful custom built guest cabin on 170 acres and private lake! This 2 bedroom, 2 bathroom home has a custom cedar sauna, jetted jacuzzi bathtub, gas grill, and a cooks kitchen. Enjoy the beauty and peacefulness of this one of a kind property! Experience nature by exploring the property's walking trails, or use the canoe, paddle boat and row boat to enjoy the lake. There is a dock and swimming raft on the pristine, spring fed lake. Please inquiry about bringing a dog.

Top Guest favourite
An open living area features a comfortable gray sectional sofa and a coffee table. A dining table for four is visible, accompanied by white chairs. Natural light fills the space through a window, while green plants and modern decor add a touch of freshness.
Guesthouse in New Glarus
4.98 out of 5 average rating, 265 reviews

Fresh & Bright Apartment Getaway in New Glarus

We would like to welcome you to our bright newly built 2nd floor above garage apartment. Located in a family friendly neighborhood, just a 10 minute walk to downtown where you will find delicious dining, unique shops and historical sites everywhere you turn. Jarod and I with our kids live in the main house. We love giving our guest privacy but may run into you as we are enjoying the weather as often as we can with our kids running around enjoying their childhood.

Top Guest favourite
A rustic red barn-style structure is surrounded by snow-covered trees, creating a serene winter scene. The building features white accents and a porch area, with snow blanketing the ground and clinging to the branches of nearby trees.
Guesthouse in Whitehall
4.96 out of 5 average rating, 143 reviews

The Granary Guesthouse @ Harvest Home Farm

Harvest Home Farm is located at the end of a dead end road nestled in a valley, just 4 miles northeast of Whitehall, Wisconsin, in beautiful Trempealeau County. The 160 acre farm has a long term focus on raising grass fed sheep and poultry. We also have a produce garden, a berry patch, and an apple orchard. The farm has 80 acres of mixed hardwoods and softwoods and an abundance of wildlife as well as a network of walking trails.

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