Holiday rentals in Middleton

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Top-rated holiday rentals in Middleton

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

Guest favourite
Guest house in Mount Horeb
Cool, Scenic Country Art Studio
Creative souls love my marvelous studio retreat, a delightful space that features tall ceilings and an open design--giving it a loft feel with 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 online reservation, must be leashed when outside, and kenneled in your absence.
1–8 SeptIndividual Host,
£101 per night
4.96 out of 5 average rating, 535 reviews
Guest favourite
Home in Madison
Cottage Suite + Whirlpool Tub.
Welcome! This Suite is perfect for traveling professionals looking for long term accommodations. *Freshly remodeled guest dedicated- full 1st floor private suite. You will enjoy a bright- enclosed front porch & a welcoming rear pergola + table & chairs -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 *Convenient location to most everything Madison.
18–25 SeptIndividual Host,
£143 per night
4.95 out of 5 average rating, 293 reviews
Guest favourite
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.
12–19 Apr
£80 per night
4.97 out of 5 average rating, 290 reviews

Popular amenities for Middleton holiday rentals

Stay near Middleton's top sights

Greenway Station3 locals recommend
Hubbard Avenue Diner14 locals recommend
Original Pancake House12 locals recommend
Willy Street Co-op—West25 locals recommend
National Mustard Museum12 locals recommend
Craftsman Table & Tap7 locals recommend

Other great holiday rentals in Middleton

Guest favourite
Guest house in Sun Prairie
Charming Milkhouse Cottage, minutes from Madison!
7–14 DecIndividual Host,
£134 per night
4.98 out of 5 average rating, 304 reviews
Guest favourite
Guest suite in Stoughton
Guest suite w/ Private Entrance & Outdoor Fire pit
21–28 Jan
£84 per night
4.92 out of 5 average rating, 167 reviews
Guest favourite
Home in Madison
Private apartment -2 Beds, Kitchen Office, Sunroom
4–11 JunIndividual Host,
£131 per night
4.88 out of 5 average rating, 206 reviews
Guest favourite
Tiny home in Darlington
The Bower- Peaceful farm stay getaway.
15–22 Sept
£84 per night
4.98 out of 5 average rating, 235 reviews
Guest favourite
Guest suite in Madison
Lakefront downtown private 3 BR. Hot tub. Sauna.
21–28 AugProfessional Host,
£717 per night
4.97 out of 5 average rating, 471 reviews
Guest favourite
Guest suite in Mount Horeb
Nestled Valley
12–19 Feb
£90 per night
4.89 out of 5 average rating, 141 reviews
Guest favourite
Guest house in Stoughton
Country cabin, birders paradise.
15–22 AugIndividual Host,
£82 per night
4.94 out of 5 average rating, 325 reviews
Guest favourite
Guest suite in Madison
DT+Bikes+Pvt Suite+Jacuzzi+Parking+Near Campus
28 Mar – 4 AprIndividual Host,
£135 per night
4.98 out of 5 average rating, 547 reviews
Guest favourite
Apartment in Mount Horeb
Klevenville Getaway -Cozy apartment near amenities
15–22 May
£98 per night
4.9 out of 5 average rating, 51 reviews
Guest favourite
Place to stay in Middleton
Vila Azul—A magnificent place to cook and gather
7–14 Nov
£355 per night
4.95 out of 5 average rating, 39 reviews
Guest favourite
Flat in Middleton
Middleton springs
26 May – 2 Jun
£223 per night
4.96 out of 5 average rating, 25 reviews
Guest favourite
Guest suite in Verona
Peaceful Guest Suite at The Retreat
5–12 Jun
£164 per night
4.94 out of 5 average rating, 66 reviews

Quick stats about holiday rentals in Middleton

Total rentals

20 properties

Wifi availability

20 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

860 reviews

Nightly prices starting at

£24 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Dane County
  5. Middleton