Holiday rentals in Madison

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Top-rated holiday rentals in Madison

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

Guest favourite
Home in Madison
Grooviest | Quiet | Close | NEW Upscale | Records!
• ALL NEW RENOVATION, BRAND NEW LINENS, TOWELS, ETC • Two floor private home • Private backyard with patio & fire pits • Two TVs, one in living room, one in dining room • Luxury Mid Century Modern Stereo Console with records, bluetooth • Over 70 classic albums to listen to (jazz, rock, classical, eclectic) • Access to over 1000 classic albums at our downtown Music Studio • Electric fireplace with multi heat settings • Full Size Kitchen, Full Size Appliances, Fully stocked • Vintage Bar Cart ;)
3–10 NovIndividual Host,
£125 per night
4.94 out of 5 average rating, 140 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
Guest favourite
Guest suite in Madison
2 Kings, 0-Hassle Checkout, Laundry, Walkable
Enjoy a hassle-free checkout! Welcome to our charming 110-year-old house, nestled in the lively east side. The entire second floor, reachable via a private entrance, is exclusively yours for your stay. Ideal for remote work with laptop-ready desks and fast internet, our home is a short walk from the animated Atwood and Willy Street districts, an easy stroll to both Lake Monona and Lake Mendota, and a quick drive to downtown. It's the perfect sanctuary following a day of traversing the city.
2–9 Dec
£116 per night
4.97 out of 5 average rating, 107 reviews

Popular amenities for Madison holiday rentals

Stay near Madison's top sights

Alliant Energy Center6 locals recommend
Henry Vilas Zoo101 locals recommend
Wisconsin State Capitol141 locals recommend
West Towne Mall48 locals recommend
East Towne Mall21 locals recommend
Kohl Center19 locals recommend

Other great holiday rentals in Madison

Guest favourite
Cottage in Dane
The Napping Farm
14–19 AprProfessional Host,
£84 per night
4.88 out of 5 average rating, 680 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 house in Stoughton
Country cabin, birders paradise.
25 Sept – 2 OctIndividual Host,
£82 per night
4.94 out of 5 average rating, 325 reviews
Guest favourite
Home in Madison
Tranquil Bay Creek Home: Ideal location
27 Aug – 3 Sept
£153 per night
4.91 out of 5 average rating, 129 reviews
Guest favourite
Guest suite in Sun Prairie
Entire Countryside Garden Suite, Peaceful Retreat
19–26 OctIndividual Host,
£110 per night
4.88 out of 5 average rating, 240 reviews
Guest favourite
Loft in Madison
Cape Cod Loft, High-Speed internet + King bed
17–24 SeptIndividual Host,
£146 per night
4.88 out of 5 average rating, 361 reviews
Guest favourite
Townhouse in Madison
Quiet Eastside Madison Home
30 Jan – 6 FebIndividual Host,
£127 per night
4.93 out of 5 average rating, 254 reviews
Guest favourite
Guest house in Mount Horeb
Cool, Scenic Country Art Studio
14–21 JulIndividual Host,
£101 per night
4.96 out of 5 average rating, 535 reviews
Guest favourite
Apartment in Madison
Sunny Downtown Condo
24 Jun – 1 Jul
£219 per night
4.98 out of 5 average rating, 105 reviews
Guest favourite
Flat in Verona
Spacious Basement Apartment near Epic and Madison
13–20 AprIndividual Host,
£139 per night
4.97 out of 5 average rating, 215 reviews
Guest favourite
Guest house in Mineral Point
Lumber Yard Cottage, a cozy retreat
1–8 Dec
£87 per night
4.94 out of 5 average rating, 173 reviews
Guest favourite
Flat in New Glarus
The Hideout In Downtown New Glarus
15–22 NovIndividual Host,
£133 per night
5.0 out of 5 average rating, 332 reviews

Quick stats about holiday rentals in Madison

Total rentals

670 properties

Rentals with dedicated workspaces

350 properties have a dedicated workspace

Rentals with a pool

40 properties have a pool

Pet-friendly rentals

230 properties allow pets

Family-friendly rentals

330 properties are a good fit for families

Total number of reviews

35K reviews

Destinations to explore

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  2. United States
  3. Wisconsin
  4. Dane County
  5. Madison