Vacation 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

An inviting open space features a large custom breakfast bar with barstools, complemented by rustic stone walls and wooden beams. Chesterfield sofas provide comfortable seating, while natural light filters through the windows, creating a warm atmosphere. Decorative elements include vintage clocks and unique wall art.

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

A scenic view of a sunset reflecting vibrant colors in the sky over a tranquil waterway. Silhouetted trees create a natural frame along the shoreline, while gentle ripples on the water's surface capture the fading light of the day.

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.

4.98 out of 5 average rating, 610 reviews

A hiking guidebook titled '60 Hikes Within 60 Miles: Madison' is displayed. The book's cover features a person standing near a rocky outcrop in a forest, surrounded by tall trees. The title and author's name are prominently displayed, highlighting the book's focus on hiking opportunities in the Madison area.

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!

4.89 out of 5 average rating, 425 reviews

The Wisconsin State Capitol is partially shrouded in fog, with its dome softly illuminated. In the foreground, a barren tree with intricate branches adds depth to the scene, contrasting against the architecture and enhancing the atmosphere of the moment.

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

Guesthouse in Mount Horeb

The cozy studio retreat is nestled at the edge of a snowy yard, framed by tall trees. Sunlight filters through the branches, casting a soft glow on the rustic wooden exterior and a small set of stairs leading to the entrance.

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

A spacious loft area features vaulted ceilings with exposed beams, allowing natural light from multiple skylights. The layout includes a designated sleeping area with a queen bed, a comfortable seating arrangement surrounding a smart TV, and a cozy nook with a pop of color from a yellow accessory.

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

Apartment 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

A vibrant yard is filled with lush greenery and blooming pink trees, creating a serene outdoor space. In the center, a small grill is positioned for cooking. A wooden fence is visible in the background, partially obscured by the embracing foliage.

Guesthouse 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

A compact kitchen area is featured, showcasing a sleek silver refrigerator and a microwave. A coffee maker is positioned nearby on a wooden counter. A whiteboard with a welcoming message is mounted on the wall, alongside a holder with various brochures and a framed decorative sign.

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

A small cottage is illuminated by warm outdoor lighting, creating a welcoming ambiance. A gravel path leads up to the door, surrounded by trees. Two white chairs are positioned nearby, inviting relaxation amid the tranquil woodland setting.

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

The interior space features a cozy studio layout with a queen-sized bed dressed in a red coverlet. Bright windows allow natural light to fill the room. A small dining area and living space are visible, with a wall clock and access to the bathroom in the background.

Apartment 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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Popular amenities for Lake Wingra vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Lake Wingra

A cozy outdoor seating area features a firepit surrounded by decorative stones. A foot in black sandals rests comfortably on the edge, while a nearby chair stands ready for use. Lush greenery, including a large tree and landscaped shrubs, creates a serene backdrop.

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!!

A brown upholstered chair is positioned alongside a vintage wooden desk, adorned with books, a plant, and a framed picture. Natural light enters through large windows, highlighting the warm tones of the room. A small stool and potted plants add character to the inviting space.

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.

A snow-covered park scene is depicted, featuring a wooden sign that identifies Orton Park. A gazebo is visible in the background, framed by large trees while the snowy landscape creates a serene winter setting.

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!

Superhost

A wooden swing bed is situated on a covered porch, featuring plush cushions and two decorative pillows. A friendly dog is relaxed on the swing, framed by green grass and trees in the background, creating a welcoming outdoor space.

4.75 out of 5 average rating, 225 reviews

Private room near downtown- The Madison room

KevinRating, 5 stars1 month ago

Angela's place was great and a great value for a weekend where I was just looking for a place to sleep. Sheets, towels and toiletries were clean and plentiful. She was very proactive in communicating what to expect, as well as being upfront about her very friendly, but not intrusive dog. Everything went very smoothly.

The sitting room features hardwood floors and a large window allowing natural light. A vintage Pepsi vending machine is positioned against the wall, alongside a small TV on a desk. Comfortable seating includes a chaise lounge and a love seat, complemented by a decorative area rug.

4.97 out of 5 average rating, 810 reviews

Private Garden Level Guest Suite

BarbaraRating, 5 stars1 week ago

I enjoyed staying at Angie’s place! Cute, confortable with everything you could ever think you needed. Enjoyed chatting to Angie who was welcoming and friendly. A shame I was only there overnight. Thanks for a comfortable stay.

Two sandhill cranes are seen walking along a paved path, surrounded by green grass and trees. Their distinctive long legs and necks are highlighted, with their feathers displaying shades of gray and brown. A vehicle is parked in the background, partially obscured by trees.

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.

A modern wet bar area is equipped with essential appliances, including a coffee maker, toaster oven, and a sleek sink. Shelving displays various dishware. A bowl of fresh apples is placed on the granite countertop, which complements the white cabinetry and red refrigerator.

4.93 out of 5 average rating, 92 reviews

1 bed suite and remote office by lake & airport

NickiRating, 5 stars1 week ago

Sabrina and her family were excellent hosts! They made sure we were able to use the lock when we checked-in, let us use their ironing board (we were in town for a wedding), and were very responsive to messages. Great stay and location!