
Holiday houses in Pleasant Springs
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Top-rated holiday rentals in Pleasant Springs
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YurtSimple
YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

Stay With Horses Escape Near Madison
Get ready for a quiet and peaceful stay. Take your pick: - 1King+1Queen Bed & 1 bath for 4 people - 1King+2Queen Beds & 2 baths for 6. (+$125 per night, contact host for payment) This home is attached to a barn with 6 Icelandic horses! Wake up to Icelandic horses just outside your window. A scenic escape with quiet mornings, fuzzy horses, and a one-of-a-kind IamGlytja experience - only 25 minutes from Madison - No horse riding allowed, owners to supervise all horse visits - No smoking / parties

Cozy Magnolia Style 2-Bedroom Home with Loft
Cozy 2BR 1900's bungalow with beautiful backyard. Step into the Magnolia style living and dining room with decorative crown molding and new floors. Large bedroom with plenty of storage and finished attic for the kids or additional guests. Mudroom with laundry and relaxing front porch add to this spacious home. Outside is the true GEM, with adorable patio area just waiting for fire pit gatherings. Located close to parks, canoe/kayak launch, eateries, and shopping. Quick drive to downtown Madison!

Cozy Lakefront Cottage With The Best View
Location, Location, Location! Incredible views! Retreat to this cozy Lake Koshkonong cottage with vaulted ceiling and southern exposure. Enjoy spectacular sunsets and views of the 10,000 acre lake from the north shore. Fish, hunt, boat, ski, swim, snowmobile, or simply soak up the sun and take in the view from this quiet retreat on a dead-end street. Fresh paint, bedding, and furniture make this little gem very comfortable. Great Walleye ice fishing right in front of this property!

Charming Waterfront Getaway | 2BR Near Madison
Unwind in this peaceful 2BR home in McFarland—perfect for a quiet getaway just 15 min from Madison 🌿 • A nature-filled, rural setting next to a small, charming campground & marina • Nestled near a scenic inlet connecting to Yahara River & Lake Kegonsa (house is not directly on lake/river) • Peaceful walking trails + beautiful scenery • Close to Lake Kegonsa State Park • Easy drive into Madison for dining & events Perfect for couples or small families looking to relax near Madison ✨

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!

Quiet country retreat
Peaceful solitude or exciting sightseeing? You’ll have the best of both worlds at this quiet country home located just outside Madison on 10 magnificent acres. After, enjoying your morning coffee, take a stroll on the grounds and enjoy the sweeping views of the pastoral landscape. Then head into Wisconsin’s state capital (23 minutes by car) for an exciting day of sightseeing. Or visit the quaint town of Cambridge (8 minutes by car) to explore its unique pottery and antique shops.

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 included. Lawn games, poker table, board games & more available!

Yahara River paradise!
Fantastic 2 bed waterfront home on a dead-end street with beautiful views of the Yahara River. Only 25 min from downtown Madison, and 5 min from Stoughton. Serene, quiet, and teeming with cranes, eagles, osprey, beaver, deer, turkey and turtles! Spend a day floating in our kayaks or fish off our pier, as the river has almost no boat traffic, averages 2'-5' deep, and has a very slow current Our brick patio was made for entertaining with 2 firepits, a grill, and a great jacuzzi!

Peaceful 2 BR/1 BA w/ patio, fireplace, pool table
• 1400 sq. ft. lower level suite • Private backyard with patio • Two TVs • Electric Fireplace • Pool table • Stocked kitchenette w/ bar seating area • Workspace • Blackout shades and curtains • On-site parking in the driveway for one vehicle • Ample street parking • 16-min drive to the 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

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.

The Dylin Hotel | Studio
● Size: 372 SQFT ● Guests: 2 Guests ● Bed: 1 Queen Bed Experience a thoughtfully designed fully furnished Studio Apartment featuring a fully equipped kitchen, in-unit laundry, Wi-Fi, smart TV and a cozy sleeping area. The Dylin is a modern aparthotel in Madison’s Cap East neighborhood, offering apartment-style comfort with hotel consistency. Perfect for travelers who want more room to relax and live like a local —ideal for short or extended stays.
Popular amenities for Pleasant Springs holiday rentals
Other great holiday rentals in Pleasant Springs

The Orchard House

Riverview Retreat

Bees on Main: sweeter than ever

Beautiful Creekside House

Spacious Home/Fenced Yard/10 Min to Madison

Glacial Drumlin Guest Suite

Quiet Country Oasis

Mid Century Modern Lake House!
Destinations to explore
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- Devil's Lake State Park
- Alpine Valley Resort
- House on the Rock
- Wisconsin State Capitol
- Lake Kegonsa State Park
- Wollersheim Winery & Distillery
- Cascade Mountain
- Governor Dodge State Park
- Lake Geneva Public Library
- Henry Vilas Zoo
- Holy Hill National Shrine of Mary
- Lake Geneva Cruise Line
- Camp Randall Stadium
- Lake Geneva Ziplines & Adventures
- American Players Theatre
- Tyrol Basin
- Chazen Museum of Art
- Overture Center For The Arts
- Dane County Farmers' Market
- Monona Terrace Community And Convention Center
- Madison Childrens Museum
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Rock Cut State Park
- Nicholas Conservatory And Gardens





