Vacation rentals in Pleasant Springs

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Top-rated vacation rentals in Pleasant Springs

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Guest favorite

Apartment in McFarland

4.96 out of 5 average rating, 132 reviews

#302 Private Apartment in Historic McFarland House

*** Our 2nd Floor is being remodeled throughout 2025 adding 4 more units to the old McFarland House This newly remodeled unit is located in the attic of the Historic McFarland House, built in 1856 in the community that bears its name. Nestled in our small suburban downtown, this unit is perfect for travelers visiting the Madison area or nomads making a pit stop in the mid-west. Only 8mi to campus or a quick commute to the capitol, McFarland is an easy exit off multiple highways and interstates.

Guest favorite

Guest suite in Sun Prairie

4.88 out of 5 average rating, 345 reviews

Entire Lower Level, Countryside Garden Suite

Welcome to our home! We have upgraded our Garden (lower) Level to host travelers much like ourselves and long-term guests. The view of our backyard is incredible! You will find yourself lost in the country, yet less than ten minutes from all the excitement that Madison has to offer. Along with a private drive and entrance, you will have 1,000 square feet of comfort all to yourselves. This property is perfect for a quiet getaway we all need from time to time. All designed with you in mind.

Guest favorite

Home in Stoughton

4.97 out of 5 average rating, 39 reviews

10 miles from Madison, WI!

Peaceful quiet neighborhood. Sit back and relax on the large private backyard with a huge deck and patio area. Enjoy the small town charm of Stoughton just mins. from Madison. Two separate family rooms. Both are equipped with comfortable seating and 4K LED smart TV's. Both TV's also have built in Chromecast, so you can cast any movie or show you want directly from your phone. Norse Park is only a block away, which includes tennis courts, a basketball court, baseball field, play ground, etc.

Top guest favorite

Home in Madison

4.97 out of 5 average rating, 194 reviews

Lakeview Loft - Downtown Madison

Stay in the heart of Madison, enjoying exclusive access to our 3rd floor suite with lake views. Located on a quiet street along the Lake Loop bike path/Lake Monona, and close to Willy Street (0.3 mi), the Sylvee (1.1 mi), the Capitol (1.7 mi), Monona Terrace (1.6 mi), and Camp Randall (3.3 mi). Self check-in with keypad and ample parking. Wifi is over 500 Mbps download/upload speeds. #ZTRHP1-2022-00022 Note: Loft is accessed by 3 flights of stairs! Space has coffee bar only (no kitchen).

Guest favorite

Home in McFarland

4.84 out of 5 average rating, 138 reviews

The little Green Birdhouse-McFarland/Monona

Adorable tiny house located just 1/2 block to Lake Waubesa with public lake access. It's a 1/2 mile walk to the Yahara bike path, access to the Capital City bike path and into downtown Madison. Spacious, open living room. Open concept kitchen with butcher block countertops. One bedroom with an attached full bath. Laminate hardwood floors throughout. 2 car parking pad. Large backyard with a firepit, brand new fence, and a nice view of the lake. The neighborhood is quiet and welcoming.

Top guest favorite

Place to stay in Brodhead

4.98 out of 5 average rating, 168 reviews

Historic Randall Schoolhouse

You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

Top guest favorite

Home in Stoughton

4.95 out of 5 average rating, 64 reviews

Yahara River paradise!

Fantastic 2 bedroom waterfront home on a dead end street, with beautiful views of the Yahara River, yet only 25 minutes from downtown Madison. Serene, quiet, and teeming with cranes, eagles, osprey, beaver, deer, turkey and turtles! Spend a day floating in a kayak or fish off our pier, as the river has almost no motorized boat traffic, averages 2-5 feet deep, and has a very slow current. You will love to sit out on our brick patio with firepit and watch the water as the sun goes down.

Top guest favorite

Home in Janesville

5 out of 5 average rating, 135 reviews

Fully Renovated 2BR 1BA Gorgeous Exec Home #8ma-R

Enjoy your stay in Janesville, WI in this fully renovated two-bedroom cozy executive home Professionally Managed by Kevin Bush! The location is central to dining, shopping, and popular Janesville spots like the Rotary Botanical Gardens. This home will truly feel like your home away from home. Located just minutes from I39 giving you easy access for day trips to Madison, Milwaukee, Chicago, and surrounding. Please check out our listing on St. George Lane for more dates. Kevin, Host

Superhost

Cottage in Edgerton

4.85 out of 5 average rating, 138 reviews

Rock River Rest | peaceful waterfront cottage

Escape the city to your private waterfront retreat. Nestled among centuries old Oaks, our expansive backyard with 125' shoreline allows for direct river access to water activities + Lake Koshkonong. Or sit back and relax while watching wildlife out the large picture windows and listening to vintage vinyl. Carefully curated amenities make the cottage perfect for a romantic getaway, remote work or artist retreat. Ideally located 30 min from Madison or a short drive from MKE + Chicago.

Guest favorite

Guesthouse in Sun Prairie

4.98 out of 5 average rating, 357 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!

Top guest favorite

Guest suite in Deerfield

4.96 out of 5 average rating, 135 reviews

Studio on the Prairie Fen

Kick back and relax at the Studio! The Studio is a 400 sq ft unique suite in the lower level of our home. A private locked entrance opens up to a sunny space with great views of a wetland beyond the backyard. Private patio to enjoy morning coffee and the sunrise. A great place to unwind and enjoy nature's beauty! We have binoculars if you love bird watching, and bikes to ride or hike the Glacial Drumlin Trail just 0.1 mile from the front door. Lic LICHMD-2021-00621.

Top guest favorite

Home in McFarland

4.88 out of 5 average rating, 149 reviews

Lovely Waterfront Two Bedroom House

Lovely two bedroom, one bath in a rural residential area of McFarland on inlet that connects to Yahara River and Lake Kegonsa (house is not directly on lake or river). The home is situated next to a charming campground and marina in nature. Walkable fishing areas. Lake Kegonsa State Park Trail is nearby for walking or snowshoeing. Just a 20 minute drive to downtown Madison! NO PARTIES. You will be asked to leave if there is any party activity seen.