Holiday rentals in Lake Wingra

4.92 out of 5 average rating, 306 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

4.98 out of 5 average rating, 419 reviews

Loft in Belleville

Mill House Retreat

The Mill House Retreat is a 2 story loft set in a park like setting next to the Sugar River. Built in 1864, this stone grist mill has soaring 15ft ceilings, original fittings and luxurious finishes. You will be greeted by chesterfield sofas, a large bar, a copper tub and comfortable beds. Just minutes to bike trails, live music, restaurants, and bars. Guests are welcome to have local friends over to enjoy the setting and reminisce. Madison, New Glarus and Epic are just minutes away.

Guest suite in Sun Prairie

4.88 out of 5 average rating, 336 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, 376 reviews

Guest suite in Madison

Cottage Suite + Whirlpool Tub.

This Suite is perfect for 1-4 people seeking convenient proximity to most things Madison 10-15 minutes to downtown. *Freshly remodeled guest dedicated- full 1st floor private suite. You will enjoy a bright- enclosed front porch & welcoming pergola in back. *Please note: 2nd floor is a seperate apartment. Fast WIFI●Infrared Sauna●2 Smart TV 's●Full Kitchen●Washer/Dryer●Dishwasher ●Off-Street parking●Quiet neighborhood ●Reverse osmosis H²O●Smart lock's●Jacuzzi tub/shower●Shampoo/Cond./Bodywash

4.98 out of 5 average rating, 610 reviews

Guest suite in Madison

DT+Bikes+Pvt Suite+Jacuzzi+Parking+Near Campus

Located in a unique pocket of DT, across from Brittingham Park, Monona Bay, Brittingham Boat Rental & a bike/walking path. You will love our welcoming neighborhood! We are a short walk from UW-Madison, Hospitals, State Street & the Capitol. We have a dog, Bella, who stay upstairs, but you could see her wandering outside. We have been inspected & are licensed with the city. ZTRHP1-2020-00027. Ask us prior to arrival about availability of our high-quality mid-drive ebikes to use when you stay!

Guest house in Mount Horeb

4.96 out of 5 average rating, 605 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.

4.97 out of 5 average rating, 186 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).

4.94 out of 5 average rating, 53 reviews

Flat in Madison

Camp Randall - FREE parking! Walk to everywhere!

Welcome! Steps from the UW, Camp Randall, Edgewood College, Vilas Zoo, the bike path system, EPIC, all 3 local hospitals, downtown, the Capitol, & the lakes. With a combined 80+ years living in Madison, we’re available to you & will do everything in our power to provide for anything you may need as our guest. We’ve raised our family in this home over the past 25 years & look forward to hosting you! We allow dogs, but I’m afraid no cats. PLEASE read the ENTIRE description before booking!

4.93 out of 5 average rating, 260 reviews

Guest house in Madison

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.

4.98 out of 5 average rating, 191 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, 754 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.

5 out of 5 average rating, 25 reviews

Flat in Madison

Cozy Garden Apartment Near it All!

Stay in comfort at this peaceful and centrally-located place. Unwind in our cozy garden oasis after a day of exploring or visiting! This stylish well-lit studio basement apartment offers the perfect blend of comfort and convenience. Centrally located in a prime Madison Monroe Street neighborhood spot near shopping, dining, and UW or Edgewood sports venues, you'll have everything you need right at your fingertips.

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Other great holiday rentals in Lake Wingra

4.97 out of 5 average rating, 490 reviews

Spacious private level with garden view and more.

BeverlyRating, 5 stars1 week ago

Outstanding Airbnb. The room was spacious, fridge was stocked with bottled water and soda. Nice little kitchenette area. Cozy wonderful sitting area near the fire place looking out at gorgeous serene gardens. We spent hours on the patio! Bed was super comfy and quality linens were appreciated. Clean bathroom with toiletries and thick large towels. Loved all the art work, stained glass and collection of books. Guest book with recommendations was very thorough. Looking forward to returning next summer! Greg and Fred were great hosts!!

4.94 out of 5 average rating, 286 reviews

Private Suite on Park & Bike Trail

NicholasRating, 5 stars2 weeks ago

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

5 out of 5 average rating, 19 reviews

Sweet, sunny room

DerekRating, 5 stars1 week ago

Greats host and a great place to stay. Will book again for future plans. Thank you for the wonderful hospitality.

4.91 out of 5 average rating, 249 reviews

Cozy 1-bedroom steps from Lake Monona

TosiRating, 5 stars2 weeks ago

This is a beautiful area to walk in and visit, a quiet neighborhood steps from the lake and parks, Michael’s place is minimalist and you will need to eat out for your meals but there are walkable eateries nearby. Very comfy bed too!

4.97 out of 5 average rating, 812 reviews

Private Garden Level Guest Suite

RebeccaRating, 5 stars1 day ago

Angie's place was clean and very comfortable with the best book assortment of any Airbnb I've ever stayed in! The neighborhood was quiet and there is a lovely park nearby that I walked around. So beautiful! Thank you for recommending Mercies for coffee and a quick breakfast nearby. It was great.

Superhost

4.77 out of 5 average rating, 207 reviews

Homeshare room near downtown - “Milwaukee room”

SergRating, 5 stars2 weeks ago

Had a lovely stay at Angela’s during a family trip. Her doggie Imogene is the greatest host in the world. Looking forward to staying again the next time I’m in Madison.

5 out of 5 average rating, 121 reviews

Adjacent University, Lovely Neighborhood, Quiet

KaoruRating, 5 stars1 week ago

Thank you very much for offering me a very quiet and private rooms to stay. I could work efficiently for the week, and the conference I organized at UW was a great success.