Holiday Rentals in Madison, WI

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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

Countryside Home Minutes To Madison - Madison, WI
9.8 117 reviews
Madison, WI
28/08 – 31/08
SG$507/nighttotal: SG$1521 (3 )

Countryside Home Minutes To Madison

3 3
apartment , Middleton
This three-bedroom apartment is situated in Middleton, Wisconsin, just 32 kilometres from downtown Madison and within a 160 kilometre radius of Milwaukee, Wisconsin Dells and Chicago. The property enjoys excellent ratings for user experience, location and cleanliness.
The apartment is ideal for larger groups, accommodating up to 10 guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, a garden, parking and a sauna, as well as activities like exploring nearby bike trails and parks.
The Dylin Hotel | Studio - Madison, WI
9.8 42 reviews
Madison, WI
06/07 – 10/07
SG$419/nighttotal: SG$1676 (4 )

The Dylin Hotel | Studio

1 2
apartment , Madison
This Dylin aparthotel studio offers a prime location in Madison's Cap East district, placing guests within easy reach of the Capitol Square and Lake Monona, with the Capitol Building approximately 700 meters away.
This fully furnished apartment provides hotel-style consistency with amenities including a fully equipped kitchen, in-unit laundry, complimentary Wi-Fi, a smart TV, and access to an on-site fitness centre, accommodating up to two guests with optional underground parking.
Spacious Country Retreat W/pool 10 Minutes To Downtown Madison! Pet Friendly! - Madison, WI
9.0 17 reviews
Madison, WI
09/10 – 17/10
SG$999/nighttotal: SG$7992 (8 )

Spacious Country Retreat W/pool 10 Minutes To Downtown Madison! Pet Friendly!

4 2
apartment , Fitchburg
This Fitchburg house, located approximately 4 kilometres from Sunnyside Park and within 10 kilometres of Vilas Park, Henry Vilas Zoo, and Lake Waubesa, offers a convenient base for exploring Madison.
This spacious 446-square-metre property boasts four bedrooms, four bathrooms, and accommodates up to ten guests, featuring a private swimming pool, tennis court, and fully equipped kitchen; free Wi-Fi is also provided.
Crane Haven - Madison, WI
10 5 reviews
Madison, WI
21/08 – 24/09
SG$136/nighttotal: SG$4624 (34 )

Crane Haven

1 1
apartment , Madison
This Madison tri-plex townhouse, situated approximately 6.4 kilometres from the city centre, offers convenient access to local hospitals and bus routes.
Sleeping six guests across three bedrooms and two bathrooms, this self-catering property features a fridge, dishwasher, private parking (one carport and one off-street space), and internet access; long-term lets (30 days to six months) are available.

Best Madison, WI holiday rentals with parking

Look Out At The Treetops At The Cozy Paoli Nest. Near Epic Systems And Madison. - Madison, WI
9.6 36 reviews
Madison, WI
18/09 – 25/09
SG$267/nighttotal: SG$1869 (7 )

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

3 2
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.
Updated 3 Bed + Office Ranch Home Close To Downtown Madison - Madison, WI
10 21 reviews
Madison, WI
28/08 – 31/08
SG$1123/nighttotal: SG$3369 (3 )

Updated 3 Bed + Office Ranch Home Close To Downtown Madison

4 3
apartment , Monona
This apartment in Monona is conveniently located just a short distance from downtown Madison, offering easy access to the city's attractions and amenities. It is also close to Lake Monona, providing access to the lake's walking paths, parks, and water activities. The apartment has received excellent user ratings, making it a popular choice for travellers.
This spacious four-bedroom home, spanning 149 square metres, can comfortably accommodate up to eight guests. Enjoy a modern and spacious living experience with a fully remodeled kitchen and bathroom, as well as a spacious screened porch, a basement with a bedroom/office and recreation room, and amenities including a gas grill, off-street parking, laundry facilities, high-speed internet, and cable TV.
Remodeled 3 Bedroom Home In Monona. Close To Downtown! - Madison, WI
9.9 107 reviews
Madison, WI
30/07 – 02/08
SG$1003/nighttotal: SG$3009 (3 )

Remodeled 3 Bedroom Home In Monona. Close To Downtown!

1 4
apartment , Monona
This charming house in Monona is ideally located just a short walk from Winnequah Park and within easy reach of other local attractions like Aldo Leopold Nature Center and Esther Beach. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The three-bedroom house, spanning 121 square metres, offers ample space for families or groups of friends. Guests can enjoy a range of amenities, including a swimming pool, a garden, and a terrace, as well as access to a water park and free Wi-Fi.
Game Room - King Suite - Theatre Room - Fireplace - Madison, WI
10 12 reviews
Madison, WI
16/08 – 20/08
SG$982/nighttotal: SG$3928 (4 )

Game Room - King Suite - Theatre Room - Fireplace

3 4
apartment , Sun Prairie
This Sun Prairie flat is conveniently located within 200 metres of local parks and amenities, a 2-minute drive from shops and eateries, and a 35-kilometre drive from Madison's Alliant Energy Center.
This spacious 279 square metre dwelling accommodates up to 12 guests with three bedrooms and three bathrooms, featuring a games room with ping pong, air hockey, and foosball, a theatre room with an 86-inch smart TV, and a walk-out deck with a gas grill.

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

Holiday Inn Madison At The American Center By Ihg - Madison, WI
8.3 1523 reviews
Madison, WI
27/06 – 04/07
SG$152/nighttotal: SG$1064 (7 )

Holiday Inn Madison At The American Center By Ihg

1 2
hotel , Madison
The Holiday Inn Madison At The American Center, An Ihg Hotel, is located near the East Towne Mall and a short drive from Dane County Regional Airport, making it a convenient base for exploring the city. This 3-star hotel receives very good user ratings for its location, cleanliness, and overall experience.
The hotel offers a range of facilities, including a swimming pool, jacuzzi, fitness centre, and restaurant, providing guests with plenty of options for relaxation and entertainment. Guests can also enjoy a terrace or balcony, a garden, and a bar, adding to the hotel's appeal.
Lakemonona Waterfront + Privatedock + Fencedyard + Hottub + Gameroom + Evcharger - Madison, WI
9.6 35 reviews
Madison, WI
16/08 – 20/08
SG$2649/nighttotal: SG$10596 (4 )

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

4 4
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.
Family-friendly Lake Waubesa Home: Boat + Swim! - Madison, WI
Madison, WI
18/09 – 25/09
SG$621/nighttotal: SG$4347 (7 )

Family-friendly Lake Waubesa Home: Boat + Swim!

3 2
house , McFarland
This family-friendly holiday home is situated in McFarland, just 14 kilometres from the University of Wisconsin-Madison and 13 kilometres from the Wisconsin State Capitol Building. The property is located in a peaceful area, perfect for a relaxing getaway.
The house has three bedrooms and three bathrooms, spanning 167 square metres and accommodating up to eight guests. It offers a range of amenities including free Wi-Fi, a fully equipped kitchen, a private bar, a sauna, a spa, and a garden.
Lakefront 4br Up North Outdoor Getaway - Best Sunset View On The Lake - Madison, WI
9.9 107 reviews
Madison, WI
06/10 – 12/10
SG$517/nighttotal: SG$3102 (6 )

Lakefront 4br Up North Outdoor Getaway - Best Sunset View On The Lake

4 2
apartment , McFarland
This lakefront property is situated in McFarland, Wisconsin, just a short stroll from Babcock Park and a pleasant bike ride from the town's extensive network of cycle paths. The apartment has received excellent ratings for cleanliness, location and user experience, making it a popular choice for travellers.
This spacious four-bedroom dwelling spans 167 square metres and comfortably accommodates up to eight guests. The apartment offers a range of amenities, including a fully equipped kitchen, a private terrace, a garden, parking, high-speed internet, and access to a pier during the summer months.

Best Madison, WI holiday rentals with air conditioning

Studio Flat ∙ 1 Bedroom ∙ 2 Guests - Madison, WI
Madison, WI
26/06 – 28/06
SG$286/nighttotal: SG$572 (2 )

Studio Flat ∙ 1 Bedroom ∙ 2 Guests

1 2
studio , Madison
This studio apartment is located just 1.5 kilometres from the University of Wisconsin-Madison campus, close to the Henry Vilas Zoo and a short drive from the American Family Insurance World Headquarters. The surrounding area is lively and offers easy access to a variety of restaurants and shops.
The studio features a queen-sized bed and can accommodate up to two guests. It includes a fully equipped kitchen, a fitness centre, a swimming pool, a hot tub, and free Wi-Fi, parking, and breakfast.
Downtown Madison Lake Mendota Historic Mansion - Madison, WI
10 4 reviews
Madison, WI
06/07 – 10/07
SG$4383/nighttotal: SG$17532 (4 )

Downtown Madison Lake Mendota Historic Mansion

1 2
apartment , Madison
This manor house is located on a private street on the shores of Lake Mendota, just under 1.5 kilometres from the Capitol Square in Madison's city centre. The property has consistently received excellent ratings for its location, cleanliness and overall experience.
The five-bedroom home can accommodate up to 10 guests, offering a range of sleeping arrangements. Guests can enjoy a private dock and beach, a sauna, a recreational room, a garden, and a fully equipped kitchen, as well as kayaks, paddleboards and a canoe for exploring the lake.
Cottage Gem: Spotless, Secluded & Bring The Dog! - Madison, WI
9.9 98 reviews
Madison, WI
28/08 – 31/08
SG$667/nighttotal: SG$2001 (3 )

Cottage Gem: Spotless, Secluded & Bring The Dog!

1 3
cottage , Madison
This Madison garden apartment is situated on the city's west side, 0.64km from Lake Mendota and 0.16km from public transport, offering easy access to the University of Wisconsin campus, the State Capitol building, and State Street.
The self-contained unit sleeps two, features a queen-size bed, fireplace, private garden with bistro set, and free parking, alongside excellent guest reviews and no cleaning fee.
Holiday Inn Hotel & Suites Madison West - Middleton By Ihg - Madison, WI
8.4 844 reviews
Madison, WI
26/06 – 28/06
SG$257/nighttotal: SG$514 (2 )

Holiday Inn Hotel & Suites Madison West - Middleton By Ihg

1 2
hotel , Madison
The Holiday Inn Hotel & Suites Madison West, An Ihg Hotel, is situated in the western suburbs of Madison, around 15 minutes from the city centre and a 10-minute drive from Middleton Municipal Airport. This 3-star hotel is rated very good by previous guests for its cleanliness, location and overall experience.
The hotel offers a range of facilities for guests, including an indoor swimming pool, a fitness centre, a spa and a restaurant. The rooms are equipped with modern amenities, such as free Wi-Fi, a microwave, a refrigerator and a coffee maker.
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