Vacation rentals in City of Middleton

4.92 out of 5 average rating, 177 reviews

A spacious sleeping area is showcased with a king bed dressed in soft linens and an earthy-toned coverlet. Decorative bedside lamps are positioned on each side, complementing the overall decor. Warm lighting from recessed fixtures gently illuminates the area.

Guest suite in Madison

Hospitality+Kitchen+Laundry+Gardens

Tastefully updated private suite on lower level of ranch. - KING bed plus twin bed, large bathroom, full kitchen, laundry W/D, work desk, dining table w/stools, comfortable furniture. Pristine clean. Close to grocery, many restaurants, parks, UW... Great for business needs (week and month long discounts!), moving to Madison, athletic events, visiting family... Tree lined street. Free parking. Owner lives on the property, but suite is private and not shared, as per Permit #ZTRHP1-2020-00004.

Guest suite in Sun Prairie

A two-story home with a mix of stone and wood siding sits on a grassy lot. Large windows allow natural light inside. A paved driveway leads to the garage, with trees and a view of open land in the background.

4.89 out of 5 average rating, 361 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, 386 reviews

A modern kitchen is highlighted by stainless steel appliances, including a large refrigerator and a gas range. Natural light filters in through the window above the sink, illuminating the light wood floors and spacious countertops. Cabinets in a subtle hue provide ample storage.

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 exterior of a rustic studio retreat showcases wooden siding illuminated by warm lights at dusk. Large windows offer glimpses of the cozy interior, while kayaks are hung on the side. Surrounding greenery creates a natural ambiance, with a gravel path leading to the entrance.

4.96 out of 5 average rating, 621 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.

An A-frame interior showcases a spiral staircase leading to the loft, surrounded by natural wood and brick accents. A large television is mounted above a fireplace, complemented by decorative plants and a wall clock. Colorful patterns can be seen in the ceiling lights.

4.94 out of 5 average rating, 176 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 is characterized by vaulted ceilings and exposed wooden beams. Natural light floods in through multiple skylights, highlighting a comfortable seating area with a gray sofa, a neutral accent chair, and a vibrant yellow pouf. A small desk and chair are positioned against one wall, while a smart TV sits across from the seating area.

4.98 out of 5 average rating, 203 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).

Superhost

A serene outdoor patio area is shown, featuring a cobblestone surface surrounded by well-maintained gardens and tall, manicured hedges. A central fountain adds visual interest, while a dining table and chairs invite relaxation. Potted plants and seasonal flowers enhance the garden's charm.

4.87 out of 5 average rating, 274 reviews

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.

4.99 out of 5 average rating, 208 reviews

A spacious studio featuring two green upholstered benches arranged on a decorative area rug. Natural light floods the room through skylights, illuminating the cozy sleeping area with a large bed and a dining nook equipped with a small table and chairs.

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

A cozy living area features a white-bricked fireplace with an arch-shaped mirror above it. A round table with two chairs stands adjacent to the fireplace, while a light blue chair is positioned nearby. Soft natural light enters through the window, enhancing the serene atmosphere.

4.98 out of 5 average rating, 367 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!

Guest suite in New Glarus

An open living area features a comfortable gray sectional sofa and a coffee table. A dining table for four is visible, accompanied by white chairs. Natural light fills the space through a window, while green plants and modern decor add a touch of freshness.

4.98 out of 5 average rating, 255 reviews

Fresh & Bright Apartment Getaway in New Glarus

We would like to welcome you to our bright newly built 2nd floor above garage apartment. Located in a family friendly neighborhood, just a 10 minute walk to downtown where you will find delicious dining, unique shops and historical sites everywhere you turn. Jarod and I with our kids live in the main house. We love giving our guest privacy but may run into you as we are enjoying the weather as often as we can with our kids running around enjoying their childhood.

4.96 out of 5 average rating, 100 reviews

A spacious guest suite showcases a queen-sized bed with soft linens and a decorative throw. A small sitting area features a dark leather chair and a round dining table. Natural light fills the room through large windows framed by light curtains.

Guest suite in Verona

Peaceful Guest Suite at The Retreat

Looking for a stunning, private retreat in the woods just 10 minutes drive from Epic campus & less than 2 miles from lovely Donald Park? This one-bedroom guest suite over a detached garage is all you need! Airy, modern farmhouse feel with full bath and tiled shower, comfortable queen-sized bed, and tiny kitchenette (mini-fridge, microwave, and hot-plate). Your worries will float away in this ultra-tranquil setting on 10 wooded acres.

5 out of 5 average rating, 135 reviews

An open-concept living space features warm wood paneling and large glass sliding doors offering views of the river. A seating area is arranged with plush cushions, and a wooden table with bar stools is positioned nearby, inviting relaxation while enjoying the serene waterfront scenery.

Cabin in Edgerton

Waterfront modern cabin w/ kayaks

NO CLEANING OR ADD ON FEES! Enjoy your own private dock including 2 kayaks. Beautiful modern riverfront cabin near Lake Koshkonong's eateries and entertainment. Soak in the gorgeous Wisconsin summer with water activities at your fingertips. The rest of the year take in the pristine wonderland views in our enclosed balcony. Only 30 minutes from Madison's world class culinary experiences, performance arts, sports & festivals.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations with great services and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for City of Middleton vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in City of Middleton

Place to stay in Middleton

A functional kitchen features light-colored cabinetry and a spacious island with a bowl of fruit at its center. Stainless steel appliances are incorporated, including a gas range and oven. Natural light fills the room through a window above the sink, creating a bright and inviting cooking space.

4.95 out of 5 average rating, 62 reviews

Elegant Stay–Premium Kitchen–Perfect for Groups

5 out of 5 average rating, 19 reviews

A spacious bedroom features a large bed with white linens and decorative pillows. A comfortable chair sits beside a small side table. Soft lighting is provided by lamps on either side of the bed, and a window allows natural light to fill the room.

Apartment in Middleton

Private yet close to everything!

A welcoming living area features a mix of seating options, including a white leather couch and two armchairs in contrasting colors. A wooden coffee table sits in the center, complemented by a decorative plant. Natural light illuminates the room, enhancing its cozy atmosphere.

4.97 out of 5 average rating, 72 reviews

Cottage gem: Spotless, secluded & bring the dog!

5 out of 5 average rating, 60 reviews

A comfortable living area is presented with a beige sofa and patterned armchairs, inviting relaxation. A wooden dining table with chairs is visible next to a large window, allowing natural light to illuminate the space. Neutral walls are complemented by a piece of artwork.

Apartment in Windsor

Golf Course View Apartment

4.77 out of 5 average rating, 70 reviews

An open living space features a dark blue sofa facing a patterned area rug. A light-colored kitchen is visible with modern appliances and bar seating at a counter. Bright overhead lights illuminate the room, while beige walls enhance the airy feel.

Apartment in Sun Prairie

Cannery Square Short Term Rentals -102 by Patriot

4.98 out of 5 average rating, 60 reviews

The kitchen features wooden cabinetry and a light-colored countertop. Essential appliances, including a microwave and refrigerator, are present. A gas stove and coffee maker are visible on the counter. Bright lighting is provided by overhead fixtures, and a waste bin is located to the side.

Apartment in Middleton

Middleton springs

4.98 out of 5 average rating, 81 reviews

A lush green yard features vibrant yellow and orange flowers blooming in clusters. Mature trees provide shade, while the background shows gentle hills and a rustic building in the distance. The scene captures a serene, rural landscape with expansive greenery.

Apartment in Verona

Private garden level studio near EPIC