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Vacation rentals in Middleton

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Top-rated vacation rentals in Middleton

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Home in Madison

4.93 out of 5 average rating, 231 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 Madison

4.95 out of 5 average rating, 344 reviews

Cottage Suite + Whirlpool Tub.

This Suite is perfect for groups of 4 or less seeking convenient proximity to most things Madison without being 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 rental. -Awesome WIFI -2 Smart TV 's -Full Kitchen -Washer & Dryer -Dishwasher -Off-Street parking -Quiet neighborhood -Reverse osmosis -Smart lock's -Whirlpool tub/shower + soaps

Rental unit in Madison

4.98 out of 5 average rating, 110 reviews

The Green Heron: Cozy nature- lover's retreat

Enjoy everything Madison has to offer, then return to our quiet neighborhood and the peaceful pond behind your cozy, comfortable, two-bedroom, lower-level apartment with a private entrance, retro kitchenette, full bath, WI-FI, Roku TV, and CAC. There's a bike/walking path just across the pond, you'll be close to Lake Monona, and the Capitol and UW-Madison are just four miles away. No matter the season, we encourage guests to step outside, take a deep breath, and enjoy the natural surroundings.

Guest suite in Sun Prairie

4.89 out of 5 average rating, 303 reviews

Entire Countryside Garden Suite, Peaceful Retreat

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.

Guest suite in Madison

4.97 out of 5 average rating, 335 reviews

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.

Home in Madison

4.97 out of 5 average rating, 149 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).

Home in Madison

4.99 out of 5 average rating, 335 reviews

Weekday Specials Beautiful 3 Bedroom Apartment!

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

Guesthouse in Madison

4.93 out of 5 average rating, 258 reviews

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.

Guest suite in Middleton

5 out of 5 average rating, 164 reviews

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.

Tiny home in Darlington

4.98 out of 5 average rating, 676 reviews

Arbor Crest Cottage- Peaceful farm stay getaway.

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.

Guest suite in Madison

4.96 out of 5 average rating, 423 reviews

Lake City Loft - Private Floor w/Spiral Staircase

Lake City Loft, with a spiral staircase entrance, encompasses the full 2nd story bungalow of a charming, remodeled 1915 home. Located on the outskirts of the eclectic Atwood neighborhood, guests will enjoy easy walking, biking, or driving access to nearby local favorite coffee shops, restaurants, breweries, & Lake Monona. The kitchenette boasts complimentary local coffee & beer that can be enjoyed on your own private balcony! We ONLY use non-toxic cleaning and toiletry products.

Guesthouse in Sun Prairie

4.98 out of 5 average rating, 344 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!

Vacation rentals for every style

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Popular amenities for Middleton vacation rentals

Free parking on premises

Air conditioning

Stay near Middleton's top sights

Hilldale Shopping Center63 locals recommend

Walgreens30 locals recommend

Whole Foods Market29 locals recommend

Pick 'n Save27 locals recommend

Willy Street Co-op—West25 locals recommend

Metcalfe's Market19 locals recommend

Other great vacation rentals in Middleton

Guest suite in Madison

4.98 out of 5 average rating, 50 reviews

Serene, spotless studio sanctuary on west side

Guest suite in Verona

4.95 out of 5 average rating, 84 reviews

Peaceful Guest Suite at The Retreat

Rental unit in Windsor

5 out of 5 average rating, 30 reviews

Golf Course View Apartment

Home in Verona

4.93 out of 5 average rating, 90 reviews

Spacious Residence with Scenic Golf Course View

Guesthouse in Mineral Point

4.94 out of 5 average rating, 238 reviews

Lumber Yard Cottage, a cozy retreat

Rental unit in Middleton

4.98 out of 5 average rating, 45 reviews

Middleton springs

Rental unit in New Glarus

5 out of 5 average rating, 374 reviews

The Hideout In Downtown New Glarus

Guest suite in Madison

4.95 out of 5 average rating, 60 reviews

Woodland Studio

Quick stats about vacation rentals in Middleton

Total rentals
20 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
750 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Frequently Asked Questions

Do house rentals in Middleton have wireless internet?
Absolutely! We offer over 10 house rentals with wireless internet in Middleton. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Middleton?
Yes! Work meets play with ease at over 10 vacation rentals in Middleton featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Middleton?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Middleton have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Middleton. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Middleton?
Middleton has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Middleton?
Experience the best of Middleton with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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