Vacation rentals in Lake Windsor

4.92 out of 5 average rating, 308 reviews

Home in Madison

Grooviest | Quiet | Close | Upscale MCM | Records!

• NEWLY RENOVATED SPACE. • Two floor upper unit in a private home • Private backyard with patio & fire pits • Flatscreen TV in living room with Chromcast and Antenna. • Luxury Mid Century Modern Stereo Console with records, bluetooth • Over 12 classic albums to listen to (jazz, rock, classical, eclectic) • Access to over 3000 classic albums at our downtown Music Studio • Electric fireplace w/ multi heat settings • Full Size Kitchen, Full Size Appliances, Fully stocked, Keurig • Vintage Bar Cart

Guest suite in Sun Prairie

4.88 out of 5 average rating, 338 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.

4.95 out of 5 average rating, 149 reviews

Townhouse in Sun Prairie

1,650 sq ft, 3 bd, 2ba Ranch - All the comforts!

Centrally located just 15 minutes to the airport, 17 mins to downtown Madison, 45 minutes to Devil’s Lake, an hour to Milwaukee. Only a mile from dozens of restaurants, Costco, Target, and a Marcus Palace theater. Feel recharged when you sleep in the luxury hybrid beds. Be at home on the patio with a drink in hand while watching the fire table and cooking on the Weber gas grill. It work calls, no worries - plug into the docking station complete with keyboard, mouse and ultra wide monitor.

Guesthouse in Mount Horeb

4.96 out of 5 average rating, 607 reviews

Cool, Scenic Country Art Studio

Creative souls love my marvelous studio retreat, a delightful one-room loft-style space featuring tall ceilings, an entire wall of sliding glass doors, kitchenette, piano, and an expansive view of a picturesque barn, pasture, and wooded hills. This amazing, heated, spacious country getaway has no plumbing— it's just a few steps across the yard to the main house guest bathroom. Come create, relax, and renew here! Well-behaved dogs, included in your reservation, must be leashed when outside.

4.89 out of 5 average rating, 426 reviews

Guest suite in Madison

Cape Cod Loft, High-Speed internet + King bed

Welcome! This property is on Madison’s funky-up & coming East side. Quiet, conveniently located residential neighborhood with great neighbors & free street parking. This 2nd floor unit is a private guest-dedicated suite with it's own kitchenette, full fridge & side entrance. Massage chair. GPS: Airport- 7 min. Wisconsin State Capitol- 12 min. Ulbrich Botanical Garden's- 5 min. Camp Randall Stadium- 16 min. Walkable to Starkweather Creek Trail. *Bike *Lyft *Uber *Nearby public bus stops

4.97 out of 5 average rating, 364 reviews

Guest suite in Madison

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.

4.97 out of 5 average rating, 187 reviews

Home in Madison

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).

4.99 out of 5 average rating, 360 reviews

Home in Madison

Beautiful 3 Bedroom, Kitchen and Patio!

Private lower level 1600sq ft apartment. Steps away from TPC Wisconsin! Follow the path to the back of the main house, here you'll find a beautiful space with large windows and plenty of natural light. Enjoy the warm gas fireplace, large flat screen TV. Make meals in the generous farmhouse kitchen. Sorry no full-size oven. Relax on the paved patio overlooking the wetlands and listen to many birds. Just a 5 min drive to the airport and close to downtown. TPC WISCONSIN OPENING 8/2023

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.

4.98 out of 5 average rating, 756 reviews

Tiny home in Darlington

Arbor Crest Cottage

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. The 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.

4.95 out of 5 average rating, 463 reviews

Guest suite in Madison

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.

Guesthouse in Sun Prairie

4.98 out of 5 average rating, 352 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!

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Other great vacation rentals in Lake Windsor

4.92 out of 5 average rating, 285 reviews

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

HilaryRating, 5 stars2 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!

4.97 out of 5 average rating, 491 reviews

Spacious private level with garden view and more.

JanRating, 5 stars3 days ago

We stayed many days and were comfortable and felt welcome the entire time. The space is very comfortable with several areas to keep things interesting. The gardens are magical. I saw squirrels, rabbits, birds. Watched a male cardinal eat from the feeder one morning. I was in heaven. Gregory was so helpful! Made sure we had everything we needed multiple times. The neighborhood is beautiful to walk thru and the neighbors were friendly. Easy driving to restaurants, entertainment etc. We recommend this accomodations and would return in a heartbeat.

4.94 out of 5 average rating, 286 reviews

Private Suite on Park & Bike Trail

NicholasRating, 5 stars3 weeks ago

Excellent hosts. Had a very nice cat. (It’s not aloud in the rooms I stayed at due to possibly allergic guests)

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.

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, 190 reviews

Private room in Columbus

HA Whitney Inn, Columbus, Wisconsin

JoyRating, 5 starstoday

We had a lovely time during our stay, our hosts were very accommodating especially with our funky train schedule! They even provided some breakfast for us which most Airbnbs don't do!