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 Oostburg

4.91 out of 5 average rating, 312 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.

Guest favourite

Guest house in Plymouth

4.97 out of 5 average rating, 116 reviews

Woodside Cottage Guest House-Close to Road America

Woodside Cottage in the Kettle Moraine forest of East Central Wisconsin offers a quiet private getaway for Road American race fans, golfers or those wanting just to have a break from the city and explore the area. This 2 bedroom guesthouse can host 8, with laundry, full kitchen, living room and outdoor fire pit. Due to family guest allergies, we are pet free. Located 4 miles from gate 4 at Road America and 20 miles from Whistling Straits golf course. WIFI available, but unreliable. 3 cars MAX

Guest favourite

Guest house in Wisconsin Dells

4.86 out of 5 average rating, 298 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 favourite

Guest house in Spring Green

4.95 out of 5 average rating, 110 reviews

Teacher’s Lounge

One bedroom suite within walking distance of downtown, beautiful Spring Green, WI. Enjoy small town living at it's best. Free Wi-fi and Chromecast TV. A/C, kitchen, & full bath. Easy parking, & access to parks, village pool, & many shops, restaurants & bars. A few miles from APT, Taliesin, House on The Rock & Gov Dodge. Pets <50 lbs welcome, they are not allowed on ANY furniture, if evidence is found of such, you’ll be charged for replacement of damaged property. $25/animal fee per visit.

Guest favourite

Guest house in Mineral Point

4.94 out of 5 average rating, 245 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 Madison

4.93 out of 5 average rating, 258 reviews

Historic guesthouse near downtown, hospital and UW

Featured on the National Register of Historic Places, this unique 1916 “granny cottage" stands behind our home in the gorgeous Village of Shorewood Hills. Centrally located, we are just a few walkable blocks from UW Hospital and Picnic Point, and walking/biking distance from UW, the Capitol, Hilldale Shopping Mall, Whole Foods and plenty of restaurants. Because we are in a quiet neighborhood, we have a 3 guest maximum. This is a place to retreat and relax and enjoy the best of Madison.

Guest favourite

Guest house in Hixton

4.96 out of 5 average rating, 115 reviews

Country Retreat. Beautiful sunsets and sunrises.

Fresh country air. Beautiful view. Cable TV. Wi-Fi. Hot Tub (chemical free). Spacious furnished kitchen. Sectional sofa with recliners. Recliner. Electric fireplace. Outdoor firepit (bring your own wood). Washer and dryer. 12 inch step into tub/shower. This beautiful getaway is attached to the family business shop. We do load trailers occasionally and will be working in shop at times. Minimal noise. 30 Minutes from Eau Claire. We are only 25 minutes from two lakes with beaches.

Guest favourite

Guest house in Milwaukee

5 out of 5 average rating, 114 reviews

Cozy Bayview Guest House - Walk to entertainment!

Our Guest House (900 sq ft) is perfect for families & groups seeking a modern space within walking distance to some of the best restaurants, bars, breweries & cafes in Milwaukee's popular Bayview neighborhood. Enjoy your stay in comfort with 2 bedrooms & 5 total beds (1 king, 4 twins). Our Guest House is located directly behind the Main House on the same lot (separate houses). Free street parking is available right outside our house with plenty of spots typically available.

Guest favourite

Guest house in Pepin

4.99 out of 5 average rating, 183 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 Clintonville

4.96 out of 5 average rating, 118 reviews

Shady Retreat

Do you want to get away and relax at the lake? Visit 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 Hudson

4.96 out of 5 average rating, 179 reviews

Cottage in historic Hudson, 5 blocks from DT

Enjoy the charm of Hudson WI while spending your nights in this lovely cottage. 5 blocks walking distance from the hub of activity, you can enjoy all that the community has to offer and come home to a cozy comfortable environment . This private setting has its own entry and parking and is a perfect for corporate rentals, friend or couple getaways. Advance notice required if bringing a pet- please review house manual for details .

Guest favourite

Guest house in Whitehall

4.95 out of 5 average rating, 131 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.