Vacation rentals in Pleasant Springs

Guest suite in Sun Prairie

4.88 out of 5 average rating, 339 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.

4.98 out of 5 average rating, 50 reviews

Guest suite in Deerfield

Glacial Drumlin Guest Suite

Welcome friends to our quiet corner of the marsh! Guest suite includes a private perennial garden entrance and patio along with a cozy kitchen, living room, bedroom and full bath. Enjoy walking through the prairie, visiting the creek, and hiking/biking the state trail while still being close to Madison, WI. Conveniently located across the street from the Glacial Drumlin State Trail 18 miles to Alliant Energy Center 17 miles to WI State Capitol Easy access to Highway 12/18 and Interstate 94

4.97 out of 5 average rating, 37 reviews

Home in Stoughton

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.

4.95 out of 5 average rating, 64 reviews

Home in Stoughton

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.

4.98 out of 5 average rating, 192 reviews

Guest suite in Middleton

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with a walk-in shower, this comfortable space has all the amenities perfect for a quick weekend getaway or a week-long business trip. The studio adjoins a house and is up a flight of stairs through a separate outdoor entrance. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

5 out of 5 average rating, 134 reviews

Home in Janesville

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

4.93 out of 5 average rating, 30 reviews

Apartment in Oregon

Private Downtown 1 Bdrm | 14 MI from Madison

* Flexible travel dates? Staying for work? Ask us about our long stay discount! * Welcome to historic downtown Oregon! Nestled in a picturesque setting, this elegant retreat combines modern comfort with historic charm. You'll be steps away from locally owned coffee and gift shops, a wine reserve, and restaurants! With convenient access to Madison (14 mi), experience the best of both worlds – small-town tranquility and urban excitement. Whether for work or leisure, welcome home!

4.96 out of 5 average rating, 78 reviews

Cottage in McFarland

Cute & Cozy Cottage

Cute and cozy two bedroom, one bath in a rural residential area of McFarland near an inlet that connects to the Yahara River and Lake Kegonsa (house is not directly on lake or river). Situated next to a charming campground & 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. Dog must be approved prior.

4.94 out of 5 average rating, 305 reviews

Home in Edgerton

Vast Lake Koshkonong Views from Pier, Deck, & Home

Our 2 Bedroom, 1 Bathroom House is located directly on the shores of Lake Koshkongong. The back deck overlooks thousands of acres of lake with endless lake views. Just steps off the deck, one can enjoy the grassy landscape leading to the lakeside fire-pit. Then continue out onto the end of the 140 foot top notch pier. The pier (seasonally of course) includes a bench on the end and stairs into the water so that you can take a refreshing swim on our sandy bottom shoreline.

4.95 out of 5 average rating, 130 reviews

Guest suite in Deerfield

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.

5 out of 5 average rating, 135 reviews

Apartment in Stoughton

Bees on Main: a Honey of a Place

Located in the heart of Stoughton's Downtown Historic District, "Bees on Main" is a lovingly renovated upstairs apartment. You'll find the Opera House, Chorus, and Stoughton's wonderful shops, restaurants, pubs, and galleries only steps away. The Yahara River and Fairgrounds are within a few blocks, and there's space on the private deck to safely store your bikes or kayaks if you want to enjoy the great outdoor activities and nature surrounding Stoughton.

Superhost

Home in Stoughton

4.93 out of 5 average rating, 15 reviews

The Orchard House

In a complex world that makes so many demands your time and attention, the Orchard House is a simple, Nordic-inspired refuge where you can be restored, reconnected, and refreshed. The Orchard House is a private retreat set on 30 acres in the Wisconsin countryside, just 20 minutes from Madison. A wood -fired hot tub set in a secluded forest clearing is available year round for outdoor soaking unless overnight low drops below 10 degrees.

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Other great vacation rentals in Pleasant Springs

4.92 out of 5 average rating, 285 reviews

1 sunny Yellow BR and lounge in Artist’s home!

HilaryRating, 5 stars5 days ago

Jan was communicative leading up to my arrival, met me at the back door as planned, and showed me the spaces available for my use. I got a key for the back door to the house as well as a key for my bedroom door, which was nice. Jan told me there was possibly going to be a second guest staying overnight in the bedroom next door to mine - I'm not sure that they ever showed, so while we would've needed to share the bathroom I did not have any trouble with that. I was just in town for an overnight and it was a perfect option for a cheap, quick stay. I will definitely keep it in mind for the future!

4.91 out of 5 average rating, 252 reviews

Cozy 1-bedroom steps from Lake Monona

NikoRating, 5 stars2 weeks ago

This was a great place to stay - location is amazing, it was very easy to walk lots of places, parking was easy, getting in and out was easy, and the space was quiet and comfortable.

Private room in Whitewater

4.99 out of 5 average rating, 349 reviews

Whitewater Night Lodging

SarahRating, 5 stars2 weeks ago

A nice quiet neighborhood for a quick overnight to the University.

4.97 out of 5 average rating, 332 reviews

Mornings with Meg in Madison ZTRHP1-2020-00006

JasmineRating, 5 stars1 week ago

Meg was a very knowledgeable hostess - gave us detial information on places to go and things to do with young kids, shared great details of the history of the area. She was wonderful with kids. She let us use the kitchen to cook meals - which was very helpful to us. She was very kind to do some of our laundry. We would definitely stay here again!

4.97 out of 5 average rating, 816 reviews

Private Garden Level Guest Suite

NoëlRating, 5 starstoday

Wonderfull hosts! Plenty to read and they even shared a drink with me 😁

5 out of 5 average rating, 9 reviews

Furnished Private Bedroom in a Spacious House - 2

BahaRating, 5 stars1 month ago

Wonderful host. Very responsive and accommodating. Privacy and cleanliness were never disturbed. Would stay here again.

Private room in Fort Atkinson

4.96 out of 5 average rating, 110 reviews

The perfect getaway, quiet and safe! Single beds!

JohnRating, 5 stars5 days ago

Highly recommend this AirBnB! I'll continue to stay at Maura's home when in the area.