Vacation rentals in Pleasant Springs

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Pleasant Springs

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Cabin in Edgerton

4.89 out of 5 average rating, 197 reviews

The Overlook on Lake Koshkonong - Custom Log Cabin

Custom Log cabin on Lake Koshkonong. Great yard for campfires & lawn games; over-sized deck to enjoy sunsets and breathtaking lake views. Lake access at public boat launch just down the road for swimming, fishing, or kayaking. Full bath with large suite featuring a king size bed & two single beds can accommodate up to 5 guests. Full bath with stand up shower in lower level and washer/dryer on site also. Kayak rentals available at the cabin. Lawn games, poker table, board games & more available!

Dec. 28 – Jan. 4

$166 CAD per night

Guest favourite

Guest suite in Madison

4.97 out of 5 average rating, 297 reviews

Private & Clean Apartment Near Downtown & Airport

Private, sunny basement unit with separate entry accessible by keycode. 1 bedroom (queen), full bath, sitting area (2 twins/king bed), desk, WI-FI, TV, mini fridge, microwave, & coffee/tea. On street parking. Kid friendly! Note: We live with kids above the apartment - you will hear us walking around & some water pipes. 2-4 mi from Airport, Capitol, & UW Campus. Walk to brunch, pub, jazz lounge, bubble tea, grocery store, park, & bike path. Licensed by City & State. Paying all taxes & fees.

Aug. 22 – 29

$176 CAD per night

Guest favourite

Yurt in Cambridge

4.97 out of 5 average rating, 544 reviews

YurtCation

YurtCation is a relaxing getaway with lake frontage and nature trails. There is another yurt about 300ft up the same driveway. There are a total of two yurts and two homes that have access to the same 17 acre lake. Each yurt is off the grid and has their own queen-sized comfy bed, wood stove, Weber grill w/charcoal, fire pit, firewood, fresh water, canoe, and clean Porto Potty. Pet Policy: Max two - Must be in your sight and supervised at all times or $500 fine and check out immediately.

Nov. 2 – 9

$196 CAD per night

Guest favourite

Guest suite in Madison

4.99 out of 5 average rating, 149 reviews

Peaceful 2 BR/1 BA w/ patio, firepit & pool table

• 1400 sq.ft. lower level suite • Private backyard with patio & gas fire pit • Two TVs • Electric fireplace • Pool and Air hockey table • Stocked kitchenette w/ bar seating area • Workspace • Blackout shades and curtains • Onsite parking in driveway for one vehicle • Ample street parking • 16-min drive to UW campus and downtown • 9-min drive to the airport • 6-min drive to shopping and restaurants • Extremely safe neighborhood • License No. LICHMD-2022-00079 • Zone Permit ZTRHP1-2022-00005

Nov. 14 – 21

$294 CAD per night

Guest favourite

Guest suite in Middleton

5.0 out of 5 average rating, 116 reviews

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with two skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with 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 but has its own outdoor entrance and is soundproofed for privacy. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

Jul. 4 – 11

$209 CAD per night

Guest favourite

Guest suite in Sun Prairie

4.89 out of 5 average rating, 247 reviews

Entire Countryside Garden Suite, Peaceful Retreat

Welcome to our home! We have upgraded our Garden 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.

Apr. 8 – 15

$133 CAD per night

Guest favourite

Guesthouse in Madison

4.92 out of 5 average rating, 245 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.

Sep. 21 – 28

$207 CAD per night

Guest favourite

Tiny homes in Darlington

4.98 out of 5 average rating, 595 reviews

Arbor Crest Cottage- Peaceful farm stay getaway.

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. Our farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

Nov. 10 – 17

$152 CAD per night

Guest favourite

Guest suite in Madison

4.96 out of 5 average rating, 358 reviews

Lake City Loft - Private Floor w/Spiral Staircase

Lake City Loft, with a spiral staircase entrance, encompasses the full 2nd story bungalow of a charming, remodeled 1915 home. Located on the outskirts of the eclectic Atwood neighborhood, guests will enjoy easy walking, biking, or driving access to nearby local favorite coffee shops, restaurants, breweries, & Lake Monona. The kitchenette boasts complimentary local coffee & beer that can be enjoyed on your own private balcony! We ONLY use non-toxic cleaning and toiletry products.

May 12 – 19

$217 CAD per night

Guest favourite

Guesthouse in Sun Prairie

4.98 out of 5 average rating, 307 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!

Feb. 2 – 9

$232 CAD per night

Guest favourite

Guesthouse in Stoughton

4.94 out of 5 average rating, 331 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.

Apr. 4 – 11

$142 CAD per night

Guest favourite

Loft in McFarland

4.97 out of 5 average rating, 114 reviews

Private Loft in Historic McFarland House

This newly remodeled unit is located in the attic of the Historic McFarland House, built in 1857 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.

Mar. 10 – 17

$194 CAD per night