Vacation rentals in City of Middleton

4.97 out of 5 average rating, 203 reviews

A branch adorned with delicate white flowers is positioned in a vase on a table, creating a soft focal point. In the background, a spacious bed is partially visible, with natural light entering from a window, enhancing the bright interior.

Loft in McFarland

#301 Private Apartment in Historic McFarland House

*** Our 2nd Floor is being remodeled throughout 2025 adding 4 more units to the old McFarland House This newly remodeled unit is located in the attic of the Historic McFarland House, built in 1857 in the community that bears its name. Nestled in our small suburban downtown, this unit is perfect for travelers visiting the Madison area or nomads making a pit stop in the mid-west. Only 8mi to campus or a quick commute to the capitol, McFarland is an easy exit off multiple highways and interstates.

4.92 out of 5 average rating, 178 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, 369 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, 166 reviews

A spacious living area features a large brown leather sectional sofa, accented with decorative pillows. A glass-top coffee table sits on a plush rug. In the background, a dining area with a modern table and light fixture is visible.

Townhouse in Sun Prairie

1,650 sq ft, 3 bd, 2ba Ranch - All the comforts!

Centrally located just 15 minutes to the airport, 17 mins to downtown Madison, 45 minutes to Devil’s Lake, an hour to Milwaukee. Only a mile from dozens of restaurants, Costco, Target, and a Marcus Palace theater. Feel recharged when you sleep in the luxury hybrid beds. Be at home on the patio with a drink in hand while watching the fire table and cooking on the Weber gas grill. It work calls, no worries - plug into the docking station complete with keyboard, mouse and ultra wide monitor.

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, 625 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.

5 out of 5 average rating, 10 reviews

A serene outdoor seating area is highlighted by four wicker chairs arranged around a round table. Lush greenery surrounds the space, and views of the tranquil lake create a peaceful atmosphere. A subtle path leads toward the water's edge, with distant docks visible.

Home in Middleton

Luxury Lakeside Oasis- 3 Bed / 3 Bath Lake Home

Enjoy time with your loved ones at our luxury lake front oasis. Breathtaking views combined with the ideal Middleton location & extensive updating make our home the perfect vacation destination. Huge windows maximize gorgeous views of 60+ feet of lake frontage. A fully updated kitchen boasts custom everything. Our home features: 3 bedrooms, 3 bathrooms, lofted office, open kitchen with an island & dining table. A short drive (5-7 mi) to UW Campus, Camp Randall, Kohl Center & Wi State Capitol

4.94 out of 5 average rating, 176 reviews

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.

Home in Madison

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.

4.98 out of 5 average rating, 82 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

Located on the IRONMAN bike loop. EPIC is a 6 min, traffic free drive. Welcome to our private garden level studio with a private walk-out entrance—ideal for workspace or relaxation. Highlights include: Private bathroom & kitchenette—perfect for light cooking and self-contained convenience. Fully equipped workout gym featuring an Airdyne bike and free weights Two flat screen TV’s for streaming. Dedicated office just off the living area—ideal for remote work, study or focused projects.

4.98 out of 5 average rating, 205 reviews

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.

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).

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.

Home in Madison

4.87 out of 5 average rating, 278 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, 210 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.

4.96 out of 5 average rating, 102 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.

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Popular amenities for City of Middleton vacation rentals

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Other great vacation rentals in City of Middleton

4.97 out of 5 average rating, 511 reviews

Spacious private level with garden view and more.

4.94 out of 5 average rating, 119 reviews

On Water in Madison-middle room

4.94 out of 5 average rating, 17 reviews

A small deck area is illuminated by soft outdoor lighting, featuring a table with two chairs. The structure is surrounded by greenery and a fence, with large glass doors providing views of the serene landscape beyond. A calm evening atmosphere is present.

Tiny home in Oregon

Le Gallus Palace - A Tiny House

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, 837 reviews

Private Garden Level Guest Suite

Home in Middleton

4.75 out of 5 average rating, 4 reviews

SMalL & CoZy

Private room in Middleton

An outdoor seating area is surrounded by lush greenery and trees. Two chairs with backs and a glass-topped table sit atop a wooden deck. A fire pit is visible in a gravel area, with a charcoal grill nearby, creating a peaceful setting.

4.95 out of 5 average rating, 152 reviews

Retreat in woods on Lake Mendota

4.94 out of 5 average rating, 104 reviews

1 bed suite and remote office by lake & airport