Holiday houses in Monona

4.92 out of 5 average rating, 307 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

Guesthouse in Mount Horeb

4.96 out of 5 average rating, 606 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 Marquette

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).

4.88 out of 5 average rating, 262 reviews

Home in Madison

Private apartment -2 Beds, Kitchen Office, Sunroom

COVID CLEANED Private Garden Apartment. Feel at home in your private lower level living space. Our home is surrounded by beautiful landscaped gardens and patios. We are located near the lake, on the lake bike loop, in the heart of Madison. Relax outside, enjoy dinner on the patio or have a bonfire. Venture out on a bike ride to the farmer's market on the Capital Square, or visit Monona Terrace, State Street, Olbrich Gardens or the Alliant Energy Center; just a short distance away.

4.84 out of 5 average rating, 130 reviews

Home in McFarland

The little Green Birdhouse-McFarland/Monona

Adorable tiny house located just 1/2 block to Lake Waubesa with public lake access. It's a 1/2 mile walk to the Yahara bike path, access to the Capital City bike path and into downtown Madison. Spacious, open living room. A brand new kitchen with butcher block countertops. One bedroom with an attached full bath. Laminate hardwood floors throughout. 2 car parking pad. Large backyard with a firepit, brand new fence, and a nice view of the lake. The neighborhood is quiet and welcoming.

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.

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!

4.99 out of 5 average rating, 101 reviews

Bungalow in Monona

Retro Charm Near DT Madison & Lake Monona

Experience the best of Wisconsin’s Capital City in this newly remodeled 1930's bungalow in one of Madison’s most desirable neighborhoods. Take the provided bikes for a spin on the famous 13-mile Lake Loop, just steps from our front door. Grab fun pool floaties and relax on Lake Monona at nearby Schluter Beach. Treat yourself to an ice cream cone at the retro ice cream parlor. When you're ready to shop or hit the farmer's market, downtown Madison is an easy 15-minute drive.

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Other great holiday rentals in Monona

4.89 out of 5 average rating, 90 reviews

Comfy 3 bedroom Cottage

LyndleyRating, 5 stars3 weeks ago

Katherine’s place was perfect for our family with kids. The neighborhood was full of families and parks, making us feel right at home. Easy to get to everything too. The place was very clean and had what we needed to make it feel like home for our stay. Bedrooms were more spacious than the photos make them look. Main living room was spacious and the couch was comfy and clean! We would definitely stay again!

5 out of 5 average rating, 18 reviews

Warm, modern family home on lake and bike path

JenniRating, 5 stars4 days ago

Very nice place for family stay in Monona. Especially nice kitchen space and amenities. Our family really enjoyed the screened patio and backyard space, as well as adorable friendly cat.

4.93 out of 5 average rating, 89 reviews

Madison Lakefront Oasis in the Heart of Madison

JacquelineRating, 5 stars2 weeks ago

This is a gem if you like to walk to local restaurant have access to all the stores you need and a need to feel surrounded by nature. The master bedroom was so wonderful with a screen door to leave open at night for fresh air, also a small balcony to view the water from bedroom. We left the outdoor summer lights on the deck that somehow reflected on the ceiling of the master bedroom at night it left a beautiful light pattern, magical place, to see turtles, birds and we saw a heron as we left the house, resting on the dock. Great location and amazing hosts! We had dinner on the grill with music it was simply perfect.- Thanks, again to our hosts! Worth it!

5 out of 5 average rating, 15 reviews

Cabin in Baraboo

SamanthaRating, 5 stars1 week ago

My two best friends and I stayed at the fabulous Refugio Graziella for a relaxing girls’ weekend and it. was. perfect. Most of the weekend was spent lounging and chatting in all the many wonderful spaces the home offers: sipping coffee on the peaceful screened-in porch, relaxing in the hot tub, roasting marshmallows at the serene fire pit under the string lights with ample firewood and supplies, doing crafts and playing games at the inviting dining room table, cooking meals in the fully equipped kitchen, and listening to music in the cozy living room. We did not end up using the sauna (just didn’t have time), but are already planning a winter getaway to RG. We absolutely loved our stay and highly recommend it if you are looking for a quiet getaway, surrounded by nature but still a short drive away from anything you need or want. Clearly, so much thought was put into anticipating the needs of their guests, and that makes Refugio Graziella a place you immediately feel comfortable. 🥰

4.66 out of 5 average rating, 197 reviews

Townhouse in Monona

Comfortable and clean 1/2 duplex near Waterfront

BrookeRating, 5 stars2 weeks ago

Great place, lots of space! Doug was very friendly & easy to contact if needed. Thanks for the nice stay.

4.93 out of 5 average rating, 74 reviews

Centrally located 4 Bedroom beautiful home

BobRating, 5 stars4 days ago

We enjoyed our stay at Henry’s place for a family wedding weekend. Great location and a beautiful, well decorated and maintained interior. Big beautiful yard as well. Lots of space to spread out, relax, and enjoy each other’s company both inside and out. Didn’t have any issues, but Henry responded very promptly to a couple inquiries before we arrived. Definitely recommend!

4.97 out of 5 average rating, 68 reviews

Wonderful 3 bed home close to downtown & the lake

LindseyRating, 5 stars3 weeks ago

Luke’s place was great! Came into town to hang out with family and this place was exactly what we needed. Easy to get to a lot of things and the surrounding area was very peaceful! We truly enjoyed our time here!