Holiday Rentals in Madison, WI

433 available vacation rental offers

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Madison, WI holiday rentals
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Best Holiday rentals and Airbnb offers in Madison, WI

Best family friendly Madison, WI holiday rentals

Among the 433 accommodations in Madison, WI, here are the 4 best family friendly rentals

Vintage Home Steps Away From Lake Mendota - Madison, WI
9.7 12 reviews
Madison, WI
01/08 – 14/09
SG$208/nighttotal: SG$9152 (44 )

Vintage Home Steps Away From Lake Mendota

1 1
apartment , Madison
This two-bedroom flat is situated in a peaceful neighbourhood, just a block from Lake Mendota and a short distance from the city centre. It has received excellent ratings for its cleanliness, location and overall experience.
The apartment can accommodate up to four guests and includes a dedicated workspace, a kitchen with a fridge and microwave, as well as air conditioning and parking. You can enjoy stunning lake views, explore the nearby Capitol Square and University of Wisconsin-Madison campus, and take advantage of easy access to public transport.
Look Out At The Treetops At The Cozy Paoli Nest. Near Epic Systems And Madison. - Madison, WI
9.6 37 reviews
Madison, WI
22/07 – 25/07
SG$361/nighttotal: SG$1083 (3 )

Look Out At The Treetops At The Cozy Paoli Nest. Near Epic Systems And Madison.

3 3
apartment , Verona
This two-bedroom apartment in Verona is situated on the top floor of a guesthouse, just a short walk from restaurants, shops, and pubs. The property has an excellent user rating and offers a peaceful retreat in a convenient location.
The apartment has one bathroom and comfortably accommodates up to six guests. It features a well-equipped kitchen, a private terrace or balcony, a garden, and a jacuzzi, ensuring a comfortable and enjoyable stay.
The Green Heron: Cozy Nature- Lover's Retreat - Madison, WI
10 174 reviews
Madison, WI
14/11 – 16/11
SG$253/nighttotal: SG$506 (2 )

The Green Heron: Cozy Nature- Lover's Retreat

2 2
apartment , Madison
This two-bedroom flat is located in a peaceful neighbourhood in Madison, just 4 kilometres from the Capitol and the University of Wisconsin-Madison, and a short walk from the Capitol City Bike Path. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The flat offers a private entrance and a mudroom for storing outdoor gear, and can accommodate up to four guests. The kitchen is equipped with a freezer and microwave oven, and the flat also benefits from air conditioning, Wi-Fi, a Roku TV, and a garden.
Capital City- 6 Miles From Madison With Fireplace - Madison, WI
9.8 43 reviews
Madison, WI
01/12 – 24/12
SG$542/nighttotal: SG$12466 (23 )

Capital City- 6 Miles From Madison With Fireplace

4 1
apartment , Sun Prairie
This apartment is located in Sun Prairie, a quiet suburb just 6km from the state capital, Madison, and within easy reach of major amenities. It has received excellent user ratings and is perfect for families and groups.
The apartment has four bedrooms and three bathrooms, comfortably accommodating up to 12 guests. It offers a range of amenities, including a fully equipped kitchen, a terrace, a garden, and parking, as well as Wi-Fi and air conditioning.

Best Madison, WI holiday rentals with parking

Pool With Slide. Great For Business Travelers! - Madison, WI
9.2 903 reviews
Madison, WI
23/07 – 31/07
SG$199/nighttotal: SG$1592 (8 )

Pool With Slide. Great For Business Travelers!

1 1
apartment , Fitchburg
The Staybridge Suites Madison - Fitchburg, An Ihg Hotel is located just half a mile from Ten Pin Alley and within a three-mile radius of Elver Park and Vitense Golfland, making it a convenient base for exploring the area. This three-star hotel has received excellent user ratings, suggesting a comfortable and enjoyable stay.
The apartment-style accommodation features a full kitchen, allowing guests to prepare their own meals. Amenities include an indoor pool, barbecue grills, a fitness centre, a restaurant and bar, and a terrace or balcony, providing opportunities for relaxation and recreation.
The Wilson I | Renovated Studio W/ Sleeping Nook - Madison, WI
9.9 75 reviews
Madison, WI
14/11 – 16/11
SG$268/nighttotal: SG$536 (2 )

The Wilson I | Renovated Studio W/ Sleeping Nook

1 2
apartment , Madison
The Wilson apartment, a two-bedroom flat in a prime Madison location, is situated within easy reach of numerous attractions, including lakes and bike trails.
This pet-friendly (dogs only) property, boasting original terrazzo floors and handcrafted furniture, offers guests a comfortable stay with a fridge, microwave, dishwasher, air conditioning, and parking; it sleeps two and is managed by a local design-focused company.
48 M² Apartment ∙ 1 Bedroom ∙ 2 Guests - Madison, WI
Madison, WI
13/09 – 31/10
SG$181/nighttotal: SG$8688 (48 )

48 M² Apartment ∙ 1 Bedroom ∙ 2 Guests

1 1
apartment , Madison
Vacation rental listing for 2 people. Your accommodation will be located in Madison.
Services and facilities: a kitchen, an iron and air conditioning. Enjoy free parking with this accommodation in Madison!
The Wilson O | Bright 2br With Custom Detail - Madison, WI
10 53 reviews
Madison, WI
01/12 – 24/12
SG$210/nighttotal: SG$4830 (23 )

The Wilson O | Bright 2br With Custom Detail

2 1
apartment , Madison
This two-bedroom apartment in downtown Madison, Wisconsin, is a short walk from the Wilson Street public parking ramp and offers easy access to James Beard award-winning restaurants and breweries.
The recently restored 1929 Georgian Revival building features original terrazzo floors, a shared roof deck overlooking local eateries, a full kitchen, and accommodates up to four guests; monthly parking is available for £150 per month.

Frequently asked questions about holiday rentals in Madison, WI

  • What should a first-time visitor not miss in Madison, WI?

    You definitely want to visit the Wisconsin State Capitol building, it's a beautiful example of architecture. The University of Wisconsin-Madison campus is also worth a stroll around, especially the Memorial Union Terrace on the shores of Lake Mendota.
  • What are the best Airbnb and vacation rentals in Madison, WI?

  • Which neighborhood in Madison, WI should you consider for a vacation rental?

    The vibrant and historic downtown area is a great choice, close to shops, restaurants, and attractions. If you prefer a more relaxed atmosphere, the east side offers a more residential feel with plenty of parks and green spaces.
  • What are the most popular Airbnbs in Madison, WI?

  • What are the top family-friendly attractions in Madison, WI?

    The Madison Children's Museum is a big hit with kids of all ages. The Henry Vilas Zoo is another popular choice, with a variety of animals and a large playground. If you're looking for something outdoorsy, the Olbrich Botanical Gardens offers beautiful walking trails and a children's garden.
  • What are the best vacation rentals with a pool in Madison, WI?

  • When is the best time to book a vacation rental in Madison, WI?

    It depends on your preferences, but the shoulder seasons, spring and autumn, offer pleasant weather and fewer crowds. If you're looking for a lively atmosphere, the summer months are popular for festivals and events.
  • What are the best rentals for families and kids in Madison, WI?

  • What events or festivals should visitors check out in and around Madison, WI?

    Madison is known for its vibrant arts and music scene. The Madison Jazz Festival takes place in June, and the Wisconsin State Fair, a large agricultural fair, is held in August. The Dane County Farmers' Market is open every Saturday from April to November.
  • What are the best rentals or Airbnbs with a jacuzzi in Madison, WI?

    The best vacation rentals or Airbnb with a jacuzzi in Madison, WI are Cottage Suite Whirlpool Tub, Quiet Eastside Madison Home and Professionally Serviced Private 1br Apartment.

  • What are the best budget-friendly activities in Madison, WI?

    The Capital City Trail is a great way to explore the city on foot or by bike. The University of Wisconsin-Madison Arboretum offers beautiful walking trails and gardens, and it's free to enter. The Madison Public Library has a variety of free events and programs throughout the year.
  • What are the best restaurants with local dishes in Madison, WI?

    For a taste of Wisconsin, try the Brat Stop, a local institution known for its brats and cheese curds. The Sconni on State Street offers a modern take on traditional Wisconsin fare. For a more upscale dining experience, the L'Etoile is a fine dining restaurant serving contemporary American cuisine.
  • What are the best walking or cycling routes in Madison, WI?

    The Capital City Trail is a 20-mile paved loop that goes around the city. The Lake Loop is a scenic route that circles Lake Mendota. For a more challenging ride, the Military Ridge State Trail is a 40-mile paved trail that follows an old railroad line.
  • Are there pet-friendly attractions in Madison, WI?

    Yes, many of Madison's parks are pet-friendly, including Olbrich Botanical Gardens and Tenney Park. The Henry Vilas Zoo offers a dog-friendly walking path. Many restaurants also have outdoor seating where pets are welcome.
  • What are the benefits of choosing a vacation rental in Madison, WI?

    Vacation rentals often offer more space and privacy than hotels, and many come with kitchen facilities, allowing you to prepare your own meals. They can also be a more budget-friendly option, especially for larger groups.
  • What are the top sports attractions and facilities in Madison, WI?

    The University of Wisconsin-Madison is known for its strong sports programs, including football, basketball, and hockey. The Camp Randall Stadium is home to the Badgers football team, and the Kohl Center is home to the Badgers basketball and hockey teams. The city also has a number of other sports facilities, including the Alliant Energy Center, which hosts a variety of events.

Destinations nearby

Best Madison, WI holiday rentals with a balcony

Entire 3 Bedroom With Fireplace - Sleeps 12 - Madison, WI
9.9 160 reviews
Madison, WI
26/07 – 30/07
SG$618/nighttotal: SG$2472 (4 )

Entire 3 Bedroom With Fireplace - Sleeps 12

3 7
apartment , Sun Prairie
This Sun Prairie home is situated just a short distance from both the American Center and Token Creek Park, offering a convenient location for exploring the area. It has received excellent ratings for location, cleanliness, and overall experience.
The property offers ample space with three bedrooms and a floor area of 204 square metres. Guests can enjoy a range of amenities including a terrace, garden, barbecue grills, a fully equipped kitchen, and free WiFi.
Lakemonona Waterfront + Privatedock + Fencedyard + Hottub + Gameroom + Evcharger - Madison, WI
9.8 37 reviews
Madison, WI
06/09 – 13/09
SG$2350/nighttotal: SG$16450 (7 )

Lakemonona Waterfront + Privatedock + Fencedyard + Hottub + Gameroom + Evcharger

4 2
apartment , Monona
This four-bedroom, three-bathroom Madison waterfront property is situated near Winnequah Park, Esther Beach, and the Aldo Leopold Nature Centre, all within 3km.
Sleeping up to 16 guests, this holiday home boasts a jacuzzi, terrace, garden, family-friendly arcade, barbecue grills, and a fully equipped kitchen; enjoy nearby lake activities and explore the local parks.
70 M² Apartment ∙ 1 Bedroom ∙ 2 Guests - Madison, WI
Madison, WI
25/06 – 25/07
SG$249/nighttotal: SG$7470 (30 )

70 M² Apartment ∙ 1 Bedroom ∙ 2 Guests

1 1
apartment , Madison
Accommodation for up to 2 people. You will stay in Madison.
Facilities and services include an elevator, a kitchen and a fridge. This apartment in Madison also has a terrace!
56 M² Apartment ∙ 1 Bedroom ∙ 2 Guests - Madison, WI
Madison, WI
25/06 – 25/07
SG$245/nighttotal: SG$7350 (30 )

56 M² Apartment ∙ 1 Bedroom ∙ 2 Guests

1 1
apartment , Madison
Accommodation for 2 guests. This accommodation is based in Madison.
Facilities and services include a terrace, a kitchen and an iron. Enjoy free parking with this accommodation in Madison!

Best Madison, WI holiday rentals with air conditioning

Doty ★ Walk To Everything -Hotel Quality- Downtown - Madison, WI
9.9 199 reviews
Madison, WI
26/06 – 28/06
SG$1733/nighttotal: SG$3466 (2 )

Doty ★ Walk To Everything -Hotel Quality- Downtown

3 5
apartment , Madison
This modern apartment is situated in the heart of downtown Madison, just a short walk from the Capitol Square, State Street, and the Kohl Center. The accommodation has received excellent ratings for location, cleanliness, and overall user experience.
The apartment features three bedrooms and a modern kitchen, comfortably accommodating up to nine guests. Guests can enjoy a fully equipped kitchen, free Wi-Fi, air conditioning, a garden, and a welcome beer in the fridge.
1br Atwood Neighborhood Flat (Upper, Shared Entry) - Madison, WI
9.8 103 reviews
Madison, WI
09/10 – 17/10
SG$295/nighttotal: SG$2360 (8 )

1br Atwood Neighborhood Flat (Upper, Shared Entry)

1 2
apartment , Madison
This Madison apartment, situated in the Atwood/Willy Street neighbourhood, is approximately 5-6 kilometres from the Capitol building, the University of Wisconsin–Madison campus, and the Alliant Energy Center.
The self-contained flat, sleeping up to four guests, comprises a bedroom, bathroom with walk-in shower, lounge/kitchen area, and private balcony; amenities include a gas stove, microwave, and complimentary snacks, plus access to a shared backyard grill.
Entire Duplex Next To Waterfront - Madison, WI
9.3 563 reviews
Madison, WI
28/08 – 31/08
SG$250/nighttotal: SG$750 (3 )

Entire Duplex Next To Waterfront

1 3
apartment , Monona
This apartment is located in Monona, within 3km of Winnequah Park, Aldo Leopold Nature Center, and Esther Beach, making it a great base for exploring the area. It has excellent user, location, and cleanliness ratings, so you can be sure of a comfortable stay. This home sleeps up to eight people with four bedrooms and a sofa bed, making it suitable for families or groups of friends. The apartment comes with amenities such as a fully equipped kitchen, a terrace, a garden, a jacuzzi, a fitness centre, and a spa, plus parking and internet access.
Sunny, Spacious Home, Conveniently Located. - Madison, WI
9.9 80 reviews
Madison, WI
14/11 – 16/11
SG$462/nighttotal: SG$924 (2 )

Sunny, Spacious Home, Conveniently Located.

1 2
bungalow , Madison
This Madison bungalow, situated in a residential neighbourhood 8–16km from the University of Wisconsin campus and the city centre, is also 24km from Epic and a short drive from the Hilldale Shopping Centre.
The 2-bedroom, 1-bathroom property sleeps six, offering a fully equipped kitchen with breakfast provisions, free Wi-Fi, and family-friendly amenities including a highchair, travel cot, and toys; secure keypad entry ensures peace of mind.
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