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

4.96 out of 5 average rating, 538 reviews

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.

16–23 Jul

$157 SGD per night
Guest favourite

Home in Madison

4.95 out of 5 average rating, 294 reviews

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.

4–11 Mar

$216 SGD per night
Guest favourite

Guest suite in Madison

4.97 out of 5 average rating, 291 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.

12–19 Apr

$113 SGD per night

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

Home in Madison

4.95 out of 5 average rating, 145 reviews

Grooviest | Quiet | Close | NEW Upscale | Records!

11–18 Dec

$188 SGD per night
Guest favourite

Guest suite in Mount Horeb

4.89 out of 5 average rating, 141 reviews

Nestled Valley

8–15 Oct

$151 SGD per night
Guest favourite

Guest suite in Madison

4.97 out of 5 average rating, 348 reviews

Lake City Loft - Private Floor w/Spiral Staircase

$176 SGD per night
Guest favourite

Guest house in Sun Prairie

4.98 out of 5 average rating, 303 reviews

Charming Milkhouse Cottage, minutes from Madison!

4–11 Mar

$207 SGD per night
Guest favourite

Guest house in Stoughton

4.94 out of 5 average rating, 327 reviews

Country cabin, birders paradise.

24–31 Jan

$124 SGD per night
Guest favourite

Tiny home in Darlington

4.98 out of 5 average rating, 238 reviews

The Bower- Peaceful farm stay getaway.

25 Sep – 2 Oct

$130 SGD per night
Guest favourite

Guest house in Belleville

4.98 out of 5 average rating, 211 reviews

Still Point Tiny House - (Zero Added Cleaning Fee)

12–19 Jun

$155 SGD per night
Guest favourite

Home in Madison

4.98 out of 5 average rating, 105 reviews

Close to UW! 4 Bdrms, Walk to restaurants

24–31 Aug

$597 SGD per night
Guest favourite

Flat in Madison

4.96 out of 5 average rating, 102 reviews

Private entry flat near Atwood neighborhood

$173 SGD per night
Guest favourite

Cottage in Arena

4.91 out of 5 average rating, 261 reviews

Sugarland Cottage

25 Apr – 2 May

$185 SGD per night
Guest favourite

Guest suite in Madison

4.95 out of 5 average rating, 205 reviews

Downtown Condo, 5 blocks from Capital, Btn 2 Lakes

23–30 Jun

$183 SGD per night
Guest favourite

Flat in Stoughton

4.96 out of 5 average rating, 113 reviews

Spacious Suite with Lake View

13–20 Feb

$175 SGD per night

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

$40 SGD before taxes and fees

Destinations to explore

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