Guesthouse vacation rentals in Wisconsin

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Top-rated guesthouse rentals in Wisconsin

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

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Guest favorite

Guesthouse in Sayner

4.98 out of 5 average rating, 177 reviews

Sauna & Peace, Pinely-Lands End at the Edge Loft!

QUIET PRIVATE zenny retreat with large screened-in deck overlooks NHAL wilderness. Ponder a pine skyline & a plethora of stars! Howling wolves, a floodlight so you can watch it snow at night. Gas grill, firetable. Rustic SAUNA. WIFI, elect FP, kitch, 2 PAIR SNOWSHOES & a trail out the door. LostCanoe Lake, WhiteSand Lake BoatLaunch&Beach, Escanaba & Lumberjack St Trails in 5min. HeartofVilas paved Trl, Fallison Lake St Trl 15min. RusticRd #60 on the way. Semi-secluded yet 8mi to BJ restaurants!

Guest favorite

Guesthouse in Ontario

4.94 out of 5 average rating, 248 reviews

Rustic cabin in an orchard at Echo Valley Farm

Rustic cabin near Wildcat Mountain State Park and the Kickapoo Valley Reserve. A quiet place to disconnect, hike, and enjoy the Driftless. The cabin has electricity, water and a non chemical port-o-let. We are a working farm specializing in herbs, teas and apples. Our Bakery is open Saturday-Sunday 9-4, May -October or order in advance off season. Enjoy the animals and the flora. Short walk from parking to the cabin; we will transport your gear if needed. We are LGBTQ owned. BIPOC welcome.

Guest favorite

Guesthouse in Wisconsin Dells

4.85 out of 5 average rating, 285 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.

Guest favorite

Guesthouse in Mount Horeb

4.96 out of 5 average rating, 583 reviews

Cool, 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.

Guest favorite

Guesthouse in Ashland

4.99 out of 5 average rating, 347 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 favorite

Guesthouse in Mineral Point

4.94 out of 5 average rating, 236 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.

Guest favorite

Guesthouse in Fish Creek

4.97 out of 5 average rating, 192 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.

Guest favorite

Guesthouse in Poynette

4.91 out of 5 average rating, 238 reviews

Simple Cabin*Lake View rustic cabin in rural WI

The Simple Cabin on Lake Wisconsin is a simple and clean space. It would be ideal for an individual or couple who are enjoying the beautiful outdoors by day, and would like a bed by night. It is 350 sq ft for the entire cabin consisting of bedroom, small full bathroom, and living area. You will enjoy 180 degrees of across-the-water views. It's a great hub for hiking with the following all within 15 - 35 minutes: Devil's Lake, Parfrey's Glen, Gibralter Rock (ice age tr) & Mirror Lake.

Guest favorite

Guesthouse in Sun Prairie

4.98 out of 5 average rating, 342 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 favorite

Guesthouse in Oostburg

4.91 out of 5 average rating, 303 reviews

Beach House

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

Guest favorite

Guesthouse in Pepin

4.99 out of 5 average rating, 177 reviews

Rustic Modern Loft - Across from Winery/Lake View

Welcome to Pepin Guest Haus! Our cozy yet modern and fresh loft has beautiful views of Lake Pepin and is walking distance to everything in town - Villa Bellezza Winery, Pepin Marina, Harbor View Cafe, The Pickle Factory, Pepin Bistro, Laura Ingalls Wilder Museum, gift shops, etc. Pepin, Wisconsin is the hidden gem of the Midwest. As your hosts, we aim to share this treasure with you. Pepin Guest Haus is nicely appointed with everything you need for a relaxing trip!

Guest favorite

Guesthouse in Stoughton

4.94 out of 5 average rating, 348 reviews

Country cabin, birders paradise.

Country cabin with small kitchen, SMALL BATHROOM, large porch, gardens and birds galore. Located in the country just south of Madison WI. Enjoy the country life, quiet yet close enough to the city to enjoy Madison's activities or Stoughton's Opera House. Sauna, Fire pit, hiking, ask about pets. WiFi is available but not reliable, this is a country setting with slow connections. Please communicate with me regarding pets before booking.