
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.

YurtSimple
YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

Dells Domes - Riverview Escape - Glamping Dome 4
Staying in a dome amidst nature is a unique experience. The circular structure offers an amazing view of the surroundings, with peaceful sounds of rustling leaves, chirping birds, and a flowing river below. The cozy dome has a queen size bed, night stands, a seating area, mini fridge, and a k-cup coffee maker & heater/ac. At night, the starry sky and nature's sounds lull you to sleep. Waking up, you feel refreshed, and the peaceful surroundings and breathtaking views leave a lasting impression.

Private guest suite on beautiful Lake Mendota
Cozy guest suite/basement apartment with separate entrance for nature lovers. Lake and capitol views from breakfast nook with microwave and mini fridge and coffeemaker. Full kitchen coming fall 2025. Quiet, woodsy, neighborhood adjacent to Governor Nelson State Park. Completely painted and updated 7/25/24. Tiki level, pier, and kayaks for guest use. People love the views, the hot tub and woods. It is a 1929 cabin so many stairs, some indoor insects and limited space. Well behaved pets welcome!

Cool, Roomy, 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.

Cool quiet country cabin on boulders and 120 acres
Funky, tidy 23 year old country cabin on 120 acres of farmland & woods in a private, quiet rural setting. It's cozy, 950 sq ft, built with stone and wood. Open concept with a two story fireplace, porch fireplace, firepit, and open loft for sleeping (1 bed), with spiral stairs, lots of windows, walnut floors and trim, oak beams and pine kitchen tops. Shower is big and open, with doors opening to a back deck for outdoor showering. Beautiful covered porch overlooking rolling meadows and woods.

Rustic Barn Loft at Oak Springs Farm
Unplug in our gorgeous barn loft above our working barn. Sleep to the sound of crickets and frogs in the pond, then wake up and pet the sheep, goats, rabbits, cats, ducks & chickens. Open floor plan, cathedral ceiling, farm decor, fire pole, sliding barn doors. Full kitchen, jetted tub, rain shower, laundry. Stone patio, fire pit. 2 bedrooms, sleeper sofa, air mattresses. Juice, coffee, and fresh eggs provided when the hens are laying. NO A/C. ABSOLUTELY NO PETS Facebook oakspringsfarmwi

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.

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!

Campo di Bella Winery & Family Farm LLC
Welcome to Campo di Bella Farmstay. We have created a private retreat above our winehouse on our farm. You will enjoy the sights and sounds of country living. Weekend Farm to Table dinners available on-site and we typically reserve seating for our farmstay guests. From December to end of March, we are only offering dinners on Friday nights. Max room rate $175.00. Please note that during winter months, we are on a private road and snowplowing may be completed by early afternoon.

Cozy, Sunny Artist's House (UW/Near West)
Our historic, art-filled home is close to the UW hospital and campus, but is located in a quiet and pretty neighborhood. Madison is known for its open-mindedness, amazing farm-to-table restaurant scene, walk- and bike-ability, and lots of performing arts for the small size of the city. We're Superhosts in our tenth year and we'd love to comfortably accommodate you. Please take the time to read our entire listing if you'll be staying with us to learn details about the house.

Real Christmas Tree Farm! Skiing nearby
Get lost in nature and stay where the magic grows on a real Christmas tree farm! Situated on rolling hills below the Baraboo bluffs, this 125 acre farm and nature preserve has several miles of hike/bike/ski trails, a private lake and two creeks. Modern home in a quiet rural neighborhood. Easy drive on beautiful country roads to the many attractions in the area--less than 10 minutes to Devil's Lake State Park, Lake Wisconsin as well as Devil's Head & Cascade ski areas.

Far Westside Home Away From Home
Your own 820 square foot space with full bathroom. Located 6.2 miles from the UW Madison. Inside, you will find a bedroom with a queen bed, living room w/a comfortable queen size sofa bed, a 54”HDTV, a kitchenette (not a full kitchen) w/a dining room table, a mini-fridge, and a library. To see a video of the space go to YouTube and search on “v=hDgEasBTxoA” (cut and paste recommended). ZTRHP1-2020-00044
Popular amenities for Middleton vacation rentals
Other great vacation rentals in Middleton

The Mill Hotel: 206 - King Suite

Modern 2 bed, 2 office house

Pet Friendly Fully Furnished 1 bedroom Oasis

Sauna | Hot Tub | EV+ | Luxury | Cozy | Private

Modern Cabin with pool, hot tub and outdoor sauna

Haney's Tavern

Lake Landing

Downtown Verona: Cozy Hideaway
When is the best time to visit Middleton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 94 | € 87 | € 109 | € 104 | € 201 | € 143 | € 110 | € 116 | € 122 | € 127 | € 118 | € 144 |
| Avg. temp | -7°C | -5°C | 1°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 3°C | -4°C |
Frequently Asked Questions
Are there family-friendly house rentals in Middleton?
Middleton has more than 10 family-friendly house rentals. 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 $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Middleton?
Four-legged friends are welcome in Middleton. Choose from more than 10 vacation rentals for guests traveling with pets.
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.
Where should I stay in Middleton?
Make yourself at home in Middleton by choosing from our most frequently booked neighborhoods. We have over 60 vacation rentals in Downtown Middleton, over 20 vacation rentals in North Lake, and over 20 vacation rentals in Parkside Heights.
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.
Do house rentals in Middleton have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Middleton. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Middleton have wifi?
Absolutely! We offer over 10 house rentals with wifi in Middleton. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Middleton have free parking?
Absolutely! We offer over 10 house rentals with free parking in Middleton. Enjoy a tailored experience with all the comforts you desire.
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 a kitchen, over 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Middleton

Total vacation rentals
Explore 30 vacation rentals in Middleton

Nightly prices starting at
Middleton vacation rentals start at € 26 per night before taxes and fees

Verified guest reviews
Over 1,020 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Middleton vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Middleton rentals

4.9 Average rating
Middleton stays are highly rated by guests—averaging 4.9 out of 5!
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- Devil's Lake State Park
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- Wollersheim Winery & Distillery
- Henry Vilas Zoo
- House on the Rock
- Kohl Center
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- Governor Dodge State Park
- Dane County Farmers' Market
- Monona Terrace Community And Convention Center
- Camp Randall Stadium
- Madison Childrens Museum
- American Players Theatre




