Guest house holiday rentals in Wisconsin

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Top-rated guest house rentals in Wisconsin

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

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Guest favourite

Guest house in Sayner

4.97 out of 5 average rating, 156 reviews

Zen out at the Loft at Lands End at the Edge!

QUIET private zenny retreat! Covered deck in treetops overlooks NHAL state forest wilderness. Ponder a skyline of pines & a plethora of stars! Howling wolves & birdwatching; a vist by Woody, our resident pileated woodpecker sure to stop by. BBQ on gas grill, sit by firetable, or suhwing! Rustic sauna WIFI elect FP kitch 2kayaks. 5min to LostCanoe Lake, WhiteSand Lake BoatLaunch&Beach, Lumberjack/Escanaba StateTrls, 15min to HeartofVilas paved 52+mi Trl. Semi-secluded yet 8mi to BJ restaurants!!

Guest favourite

Guest house in Mount Horeb

4.97 out of 5 average rating, 550 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 favourite

Guest house in Hayward

5.0 out of 5 average rating, 108 reviews

Silent Sports Retreat in Seeley

The dog-friendly Hollywood Hills Chalet is a charming guest cabin that provides opportunities to ski, snowshoe, fat bike, MTB and hike out the door on our neighborhood trail network that is groomed in the winter. In warmer weather, the Namekagon River is less than a mile away and nearby Silverthorn Lake Park in Seeley offers great opportunities to paddle, or just chill on a family-friendly beach. Parking for 2-3 vehicles and a smaller standard trailer. (Nonsmokers only, please and thank you.)

Guest favourite

Guest house in Ontario

4.97 out of 5 average rating, 286 reviews

Rustic Spring Cabin at Echo Valley Farm

Next to a spring and gardens. Simple glamping with electricity, wood burning stove and water. Grill and fire pit available. Parking for 1 car 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, getting "unhooked" and back to Nature. This cabin is located near another farm resident's cabin. Bakery's open on Sat.Sun, May - October or order in advance in off season. LGBTQ owned.

Guest favourite

Guest house in Mineral Point

4.94 out of 5 average rating, 190 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 favourite

Guest house in Ashland

4.99 out of 5 average rating, 316 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

Guest house in Clintonville

4.95 out of 5 average rating, 103 reviews

Shady Retreat

Do you want to get away and relax at the lake? Come and stay at Shady Retreat, an updated guest house on an 86 acre lake. It has one king bed, 1 bath with a sofa sleeper. The kitchen includes a fridge, stove, microwave and a dishwasher! There are three kayaks, a paddleboard, a pedal boat and a pier for your use. It is close to supper clubs, pubs with great food and 45 minutes from Lambeau Field. Enjoy star gazing while sitting around the fire roasting marshmallows.

Guest favourite

Guest house in Pepin

4.99 out of 5 average rating, 142 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 favourite

Guest house in Stoughton

4.94 out of 5 average rating, 333 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.

Guest favourite

Guest house in Whitehall

4.96 out of 5 average rating, 121 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.

Guest favourite

Guest house in Sheboygan

4.83 out of 5 average rating, 372 reviews

Carriage House Sheboygan, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!

Guest favourite

Guest house in Viroqua

4.98 out of 5 average rating, 128 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).