Holiday rentals in Madison
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Quick stats about holiday rentals in Madison
Total holiday rentals
Explore 730 holiday rentals in Madison
Nightly prices starting at
Madison holiday rentals start at $13 SGD per night before taxes and fees
Verified guest reviews
Over 44,990 verified reviews to help you choose
Family-friendly holiday rentals
320 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 270 rentals that welcome pets
Holiday rentals with a pool
60 properties feature pools
Rentals with dedicated workspaces
430 properties have a dedicated workspace
Wifi availability
710 of Madison holiday rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Lake access and Gym across Madison rentals
4.8 Average rating
Madison stays are highly rated by guests – averaging 4.8 out of 5!
Nearby attractions
Madison’s top spots include Henry Vilas Zoo, Wisconsin State Capitol and Olbrich Botanical Gardens
Top-rated holiday rentals in Madison
Guests agree: these stays are highly rated for location, cleanliness and more.
YurtSimple
YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery
LocationFamilyDecor
Cottage Suite + Jacuzzi Bathtub & Sauna
This Suite is perfect for 1-5 people seeking convenient proximity to most things Madison 10-15 minutes to downtown. *Freshly remodeled guest dedicated- full 1st floor private suite. You will enjoy a bright- enclosed front porch & welcoming pergola in back. *Please note: 2nd floor is a seperate apartment. Fast WIFI●Infrared Sauna●2 Smart TV 's●Full Kitchen●Washer/Dryer●Dishwasher ●Off-Street parking●Quiet neighborhood ●Reverse osmosis H²O●Smart lock's●Jacuzzi tub/shower●Shampoo/Cond/Bodywash
FamilyValueBack garden
ONE OF A KIND vacation rental with a view
Arbor Hill House - Unique A-frame vacation rental perched atop a hill with great views overlooking the Beltline, UW Arboretum and the city of Madison. Excellent central location with easy access to all of Madison and surrounding areas. I'll be happy to do whatever I can to make your stay a pleasant one. Please keep things clean and be respectful. The home should not be used for parties or events. If you have any questions please feel free to ask. I look forward to sharing my home with you.
FamilyValueAccess
Lakeview Loft - Downtown Madison
Stay in the heart of Madison, enjoying exclusive access to our 3rd floor suite with lake views. Located on a quiet street along the Lake Loop bike path/Lake Monona, and close to Willy Street (0.3 mi), the Sylvee (1.1 mi), the Capitol (1.7 mi), Monona Terrace (1.6 mi), and Camp Randall (3.3 mi). Self check-in with keypad and ample parking. Wifi is over 500 Mbps download/upload speeds. #ZTRHP1-2022-00022 Note: Loft is accessed by 3 flights of stairs! Space has coffee bar only (no kitchen).
FamilyValueGetting around
Peaceful, artistic home in the heart of downtown
This inviting, historic home is situated in the most walkable, friendly neighborhood in the city. Just around the corner is a local co-op, loads of quality restaurants, cafes, coffee shops, a park, and easily accessible public transportation. The Capitol and State Street are only about a mile away, making this an ideal location for people in town for business or pleasure. Bright, peaceful, cozy, and outfitted with every convenience in mind, this property will make any guest feel at home.
LocationFamilyDecor
Madison Lakefront Oasis in the Heart of Madison
Enjoy all that Madison has to offer from this beautiful lakefront property. BRING YOUR BOAT, our private dock on Yahara River has 3 slips with access to both Lake Monona & Lake Waubesa. Central location offers multiple restaurants, shops & public boat launch all within walking distance. Breath-taking sunsets over the lake. Quick 5-10 minute commute to downtown Madison, UW-Campus, Hospitals, Alliant Energy & Sylvee, State Street, hundreds of other Madison attractions east or west side!
ValueFamilyParking
Quiet sunlit studio near vibrant downtown
This architect-designed studio is bathed in natural light, with skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with a walk-in shower, this comfortable space has all the amenities perfect for a quick weekend getaway or a week-long business trip. The studio adjoins a house and is up a flight of stairs through a separate outdoor entrance. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.
FamilyValueBack garden
Downtown Lake Monona Haven | SUPs, Hot Tub & Sauna
Stay in your private 3BR, 2BA section of our lakefront home. Paddle from the dock, relax in the hot tub or sauna and enjoy mornings on the balcony with coffee. You’re moments from Willy Street restaurants and right on the bike path. Inside, find a full kitchen, comfy living spaces. Two parking spots included. Spend days on the water or exploring the city and evenings grilling or roasting marshmallows by the fire. Paddleboards included. Pontoon rental available in warmer months.
LocationFamilyKitchen
Comfortable Madison Area Retreat In The Trees
Tri-level duplex centrally located in Fitchburg. Nestled in a quiet residential neighborhood backing up to a small patch of woods for privacy. Feel away from it all with the sights and sounds of nature yet close to all the modern conveniences. Enjoy separated living spaces, a fully equipped kitchen (per WI health code, edible cooking supplies are not allowed–we do provide untamperable salt and pepper), 3 bedrooms, 2 full bathrooms, fully stocked laundry room and attached garage!
ValueFamilyParks
The Wilson Unit F | Handcrafted Downtown Retreat
Located within The Wilson, this tucked-away third-floor corner studio offers a charming downtown stay. Historic charm meets handcrafted warmth, with woodworking details and cozy design touches. The unit faces the empty lot and may occasionally experience trucks moving gravel. Guests enjoy the shared rooftop deck overlooking nearby restaurants and nightlife. Hosted by a local husband-and-wife team passionate about thoughtful spaces. Third-floor walk-up and paid parking nearby.
ValueLocationParking
The Orchard House at Pied Beauty Farm
In a complex world that makes so many demands your time and attention, the Orchard House is a simple, Nordic-inspired refuge where you can be restored, reconnected, and refreshed. Midweek special: $1000 for 5 nights, Sunday evening through Friday morning. The Orchard House is a private retreat set on 30 acres in the Wisconsin countryside, just 20 minutes from Madison. A wood -fired hot tub set in a secluded forest clearing is available year round for outdoor soaking.
FamilyValueView
It's called the Annex-right next door to us!
The house is located in a quiet and friendly neighborhood. Community parks and city pool within 2 blocks of of the home. Close to all schools, library, parks and bike paths. Very safe and enjoyable neighborhood. Many good restaurants in the area and lots of things to do in the area Two bedrooms are upstairs with its' own bathroom. House is air conditioned and has a full and complete kitchen. The washer/dryer are located in the basement and guest have full access to it
ValueLocationBack garden
Popular amenities for Madison holiday rentals
Other great holiday rentals in Madison
Private yet close to everything! NEW
LocationFamilyNearby
Brittingham Cottage - Steps to the Beach -1.5 Bath
LocationFamilyQuiet
The Pines at Oak & Ember Luxury Micro Resort
FamilyLocationHot tub
Downtown Apt - Steps from sushi and pizza!
LocationFamilyParking
Guesthouse in Rural Mount Horeb
BathroomComfortHospitality
Quiet, Peaceful A-Frame Chalet
LocationFamilySleep quality
Waterfront Bungalow in Atwood-Willy Downtown
ValueFamilyComfort
Edgewater Escape
LocationFamilyOutdoor spaces
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $139 SGD | $146 SGD | $160 SGD | $164 SGD | $185 SGD | $183 SGD | $183 SGD | $182 SGD | $179 SGD | $173 SGD | $174 SGD | $152 SGD |
| Avg. temp | -7°C | -5°C | 1°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 3°C | -4°C |
Frequently Asked Questions
What are the best places to stay in Madison?
Staying around downtown Madison, the Capitol Square, or the University of Wisconsin–Madison area helps visitors explore local dining, arts, and lakeside walks. Near East and Monroe Street neighborhoods are also frequently suggested for a blend of residential charm and vibrant amenities.
What are the best things to do in Madison with kids?
Families often explore the Henry Vilas Zoo, interactive learning at the Madison Children's Museum, and frolic in parks by Lake Monona. Picnic areas, playgrounds, and bike paths help keep young travelers engaged.
What are some of the best things to do in Madison?
Explore the State Capitol, walk or bike around Monona Terrace, and discover art at the Chazen Museum of Art. Lakeside parks, farmers markets, and the lively State Street area create a distinct local experience.
How is the weather in Madison?
Madison has cold winters, with January temperatures around 12–27°F (-11–-3°C), and warm, humid summers, reaching 62–82°F (17–28°C) in July. Spring and autumn bring milder conditions and changing foliage, so consider layering clothing for unpredictable shifts.
What are the best places to visit in Madison?
The State Capitol, Olbrich Botanical Gardens, and the University of Wisconsin–Madison Arboretum are frequently suggested for their scenery and activities. Many visitors also walk State Street for local shops, cafes, and markets.
What are some hiking trails in Madison?
Explore the trails at the UW–Madison Arboretum, picnic along paths at Picnic Point, or stroll through Turville Point Conservation Park. These areas have forested, lakeside, and prairie landscapes for all levels.
What are some family activities we can do in Madison?
Discover wildlife at Henry Vilas Zoo, take hands-on workshops at the Madison Children's Museum, or rent paddleboats at one of the local lakes. Many parks and gardens offer space for play and relaxation.
What are some of the best day trip ideas from Madison?
Explore state parks near the region, visit local farms and orchards, or discover historic small towns known for artisan shops. Outdoor enthusiasts often hike, bike, or kayak in natural reserves around the area.
Are there any pet friendly accommodations available in Madison?
Many accommodations in Madison welcome pets, especially within downtown and near-campus neighborhoods. You can find walks in lakeside parks, off-leash dog areas, and pet-friendly patios throughout the city.
What are some local tips for visiting Madison?
Local farmers markets, especially around the Capitol, highlight regional produce and cheeses. Consider bringing a bike, as Madison has extensive cycling paths, and keep a lightweight jacket handy due to shifting lakeside weather.
What is Madison known for?
Madison is known for its lakes, vibrant campus culture, and progressive local food scene. The city is a hub for environmental research and hosts a range of festivals throughout the year.
What are the best hidden gems to explore in Madison?
Allen Centennial Garden, the Lakeshore Nature Preserve, and the quirky National Mustard Museum are distinct sites many visitors discover off the usual path. Local bookstores, bakeries, and galleries can be found in residential neighborhoods.
What are the best foods to try in Madison?
Locally sourced cheese curds, bratwurst, and Friday fish fries are frequently suggested, reflecting Wisconsin food traditions. Try fresh farmers market produce, craft brews, and inventive dishes from neighborhood bistros.
What should I bring for a trip to Madison?
Pack layers for changing Midwestern weather, as temperatures can shift from cool mornings to warm afternoons. Comfortable walking shoes and a light rain jacket are useful for exploring parks, markets, and downtown neighborhoods.
What is the nightlife in Madison like?
Madison has a lively nightlife centered around State Street, the campus area, and Willy Street, with music venues, craft breweries, and late-night cafes. Local performances, open-mic nights, and gastropubs welcome a range of tastes.
What are the most popular events or festivals in Madison?
The Dane County Farmers’ Market around Capitol Square is a seasonal favorite, while events like Art Fair on the Square and summer concerts draw lively crowds. The city also celebrates local music and food festivals, especially in warmer months.
Are there family friendly vacation rentals in Madison?
Many vacation rentals in Madison are suitable for families, especially around the Capitol, university neighborhoods, and lakeshore areas. Parks, playgrounds, and casual dining nearby help make family visits comfortable.
When is the best time to visit Madison?
Late spring through early autumn is often recommended for Madison, with comfortable temperatures, outdoor festivals, and active lake life. Autumn showcases bright foliage and a lively college-town atmosphere.
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- Devil's Lake State Park
- House on the Rock
- Noah's Ark Waterpark
- Wisconsin State Capitol
- Lake Kegonsa State Park
- Mirror Lake State Park
- Glacier Canyon Lodge
- Wollersheim Winery & Distillery
- Cascade Mountain
- Governor Dodge State Park
- Henry Vilas Zoo
- Camp Randall Stadium
- American Players Theatre
- Chazen Museum of Art
- Tyrol Basin
- Overture Center For The Arts
- Dane County Farmers' Market
- Monona Terrace Community And Convention Center
- Madison Childrens Museum
- Ho-Chunk Gaming Wisconsin Dells
- Cave Of The Mounds Lowest Point
- Parfrey's Glen State Natural Area
- Blue Mound State Park
- Tommy Bartlett Exploratory