Vacation rentals in Middleton

4.92 out of 5 average rating, 296 reviews

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

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, 330 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, 372 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

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, 600 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, 357 reviews

The exterior of Tip Top Tavern is showcased, featuring a brick façade with large windows framed by black awnings. A bright yellow sign is prominently displayed above the entrance, providing a welcoming atmosphere. The entryway includes a tile pathway that leads to the door.

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.

The A-frame structure is showcased at dusk, with large windows reflecting warm light. The architectural design highlights slanted rooflines and wooden elements, surrounded by trees, creating a serene and inviting atmosphere.

4.95 out of 5 average rating, 169 reviews

ONE OF A KIND vacation rental with a view

Arbor Hill House - Unique A-frame vacation rental perched atop a hill with great views overlooking the Beltline, UW Arboretum and the city of Madison. Excellent central location with easy access to all of Madison and surrounding areas. I'll be happy to do whatever I can to make your stay a pleasant one. Please keep things clean and be respectful. The home should not be used for parties or events. If you have any questions please feel free to ask. I look forward to sharing my home with you.

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.

4.97 out of 5 average rating, 182 reviews

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).

The image captures a vibrant downtown scene at dusk, featuring the prominent dome of the State Capitol building, illuminated against a twilight sky. Surrounding buildings and streets are softly lit, revealing their architectural details and creating a lively urban atmosphere.

4.99 out of 5 average rating, 354 reviews

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

4.93 out of 5 average rating, 260 reviews

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, 188 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.

Guesthouse in Sun Prairie

An expansive garden area is seen, featuring several rectangular planting beds arranged in a grid pattern. A wooden table sits centrally, surrounded by vibrant greens and blooming flowers, with a backdrop of lush farmland extending into the horizon under a clear sky.

4.98 out of 5 average rating, 351 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, 361 reviews

Tiny home in Darlington

The Bower- NEW baby goats! Farm Stay

Thank you for checking out The Bower at Arbor Crest Acres! We would be happy to host you! We are headed into our 6th year hosting and have enjoyed it so much! The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The Bower is just inside the property on the edge of the woods. We invite you to explore the property and enjoy the animals. The west end of the land over looks town and is a great place to watch the sunset and the goats graze.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Middleton vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Middleton

4.92 out of 5 average rating, 189 reviews

A hot tub is shown in the foreground, its water illuminated in soft light. Behind, a cottage is visible with large windows revealing a warm, inviting glow. The exterior is adorned with twinkling lights that enhance the cozy atmosphere of the setting.

Home in Poynette

Island View Hideaway-Peaceful, On Water, Sandbars!

4.88 out of 5 average rating, 147 reviews

A spacious bedroom features a large bed draped in a bright yellow blanket, complemented by a set of pillows. Windows allow natural light, while a plant adds a touch of greenery. A TV is positioned on a wooden stand, enhancing the room’s functional layout.

Home in McFarland

Lovely Waterfront Two Bedroom House

4.88 out of 5 average rating, 215 reviews

Home in Wisconsin Dells

Spacious Pine Cabin at Island Pointe

4.99 out of 5 average rating, 107 reviews

A spacious shower is enclosed in a clear glass stall, featuring built-in shelves for toiletries. Soft, neutral tones dominate the room's decor, complemented by neatly arranged towels stacked on a wooden bench. A small window allows natural light to enter, enhancing the overall brightness.

Home in Union Center

Charming country home - great vacation area.

Cottage in Richland Center

A charming cottage, originally a feed mill, is nestled in the rolling hills of the Driftless area. Lush greenery surrounds the property, while a tranquil pond reflects the natural landscape, complementing the blue sky and gentle clouds above.

5 out of 5 average rating, 191 reviews

Beautiful 1 Bedroom Cottage Tucked Away in the Hills of the Driftless Area

4.9 out of 5 average rating, 143 reviews

A fire pit is surrounded by several adirondack chairs on a stone patio. The log cabin is positioned in the background, illuminated by warm light as dusk settles. Green hills and trees provide a natural backdrop, enhancing the outdoor setting.

Cabin in Richland Center

The Driftless Escape! Modern, large cabin/57 acres

4.99 out of 5 average rating, 135 reviews

Open kitchen space is highlighted by wooden shelves displaying plates and glassware. A coffee maker sits on the granite countertop alongside a holder for sugar packets. Natural light enters through a nearby window, enhancing the inviting ambiance.

Home in Poynette

Spring has sprung at Beach Garden Bungalow!