Family-friendly vacation rentals in Madison

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Top-rated family-friendly rentals in Madison

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favourite

Guesthouse in Mount Horeb

4.97 out of 5 average rating, 546 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.

Jun. 7 – 14

$173 CAD per night

Guest favourite

Loft in Belleville

4.98 out of 5 average rating, 379 reviews

Mill House Retreat

The Mill House Retreat is a 2 story loft set in a park like setting next to the Sugar River. Built in 1864, this stone grist mill has soaring 15ft ceilings, original fittings and luxurious finishes. You will be greeted by chesterfield sofas, a large bar, a copper tub and comfortable beds. Just minutes to bike trails, live music, restaurants, and bars. Guests are welcome to have local friends over to enjoy the setting and reminisce. Madison, New Glarus and Epic are just minutes away.

Feb. 8 – 15

$453 CAD per night

Guest favourite

Farm stay in Plain

4.94 out of 5 average rating, 183 reviews

Grateful Farms Cabin: Hills, Creek, Gorgeous Views

Fully-renovated 1890s cabin located on a 60+ acre farm just north of Spring Green. The cabin has radiant floor heat, is air conditioned, has a small kitchenette, bathroom with shower, and wireless internet. The farm has a barn from 1895, a main home built in 1923, apple trees, hiking trails, creek with a swimming hole, and a large hill with marvelous views. Make this your private weekend cabin or a longer-term retreat. Farm powered primarily by a large solar array atop one of the barns.

Nov. 11 – 18

$218 CAD per night

Guest favourite

Cottage in Arena

4.91 out of 5 average rating, 263 reviews

Sugarland Cottage

The Sugarland cottage is designed to accommodate up to 8 guests. It has a full kitchen, bathroom with shower, two bedrooms, one with a queen bed and the other with a double and 2 twin beds. Downstairs is a pull out queen sized Murphy bed. Situated in a major southern Wisconsin tourism area, Sugarland cottage is close to the Wisconsin River and only 30 minutes from Madison and 10 minutes from Spring Green home of Frank Lloyd Wright’s Taliesin, American Player’s Theater, and House on the Rock.

Mar. 2 – 9

$209 CAD per night

Guest favourite

Yurt in Cambridge

4.97 out of 5 average rating, 545 reviews

YurtCation

YurtCation is a relaxing getaway with lake frontage and nature trails. There is another yurt about 300ft up the same driveway. There are a total of two yurts and two homes that have access to the same 17 acre lake. Each yurt is off the grid and has their own queen-sized comfy bed, wood stove, Weber grill w/charcoal, fire pit, firewood, fresh water, canoe, and clean Porto Potty. Pet Policy: Max two - Must be in your sight and supervised at all times or $500 fine and check out immediately.

Jul. 21 – 28

$198 CAD per night

Guest favourite

Apartment in Madison

4.98 out of 5 average rating, 153 reviews

Mendota Lake View Flat

Mendota Lake View Flat is located in the heart of James Madison Park neighborhood of Downtown Madison - just a few blocks to State Street and the Wisconsin State Capitol square. Enjoy panoramic park views of the park with plenty of space to live and work. You will love the original 1920's charm with a mix of mid century and modern flavor throughout the flat. City of Madison Permit # ZTRHP2-2021-00010 7-night minimum for June 1 - Nov 28 30-night minimum for Dec - May

Oct. 3 – 10

$741 CAD per night

Guest favourite

Guest suite in Madison

4.97 out of 5 average rating, 482 reviews

Lakefront downtown private 3 BR. Kayaks. Hot tub.

Stay in your own private 3 BR, 2 bathroom section of our lakefront downtown home. Not only will you have lake access, but you'll be steps away from amazing restaurants. In addition to being in the Willy Street neighborhood, we are on the bike path and a short walk to anywhere downtown. Don't feel like going out? Take a hot tub, sauna, kayak/paddleboard, have a cup of coffee on the dock, or roast marshmallows by the campfire. Or rent our pontoon for an additional fee.

Oct. 28 – Nov. 4

$887 CAD per night

Guest favourite

Home in Madison

4.98 out of 5 average rating, 105 reviews

Close to UW! 4 Bdrms, Walk to restaurants

- Clean, uncluttered home - Chef's kitchen, 2 separate living areas, 4 bedrooms, 2 bathrooms and a dining room - Walkable, historic neighborhood. Restaurants, coffee shops, and a neighborhood bar all within 2 blocks. - Covered front porch and open back deck - Off-street parking for up to 3 cars - 1 mile (20 min. walk) from University of Wisconsin-Madison campus and Camp Randall - 2 miles from downtown Madison - Family friendly amenities (toys, outdoor playground)

Aug. 23 – 28

$719 CAD per night

Guest favourite

Guest suite in Madison

4.98 out of 5 average rating, 554 reviews

DT+Bikes+Pvt Suite+Jacuzzi+Parking+Near Campus

We are located in a unique pocket of downtown Madison, directly across from Brittingham Park, Monona Bay, Brittingham Boat Rental & a bike/walking/running path. We are a short walk from UW-Madison, Hospitals, State Street & the Capitol. You will love our welcoming neighborhood! We have a friendly dog, Bella, who stay upstairs with us, but you could see her wandering outside. We have been inspected and are licensed with the City of Madison. ZTRHP1-2020-00027.

Jul. 19 – 26

$288 CAD per night

Guest favourite

Guesthouse in Stoughton

4.94 out of 5 average rating, 331 reviews

Country cabin, birders paradise.

Country cabin with small kitchen, SMALL BATHROOM, large porch, gardens and birds galore. Located in the country just south of Madison WI. Enjoy the country life, quiet yet close enough to the city to enjoy Madison's activities or Stoughton's Opera House. Sauna, Fire pit, hiking, ask about pets. WiFi is available but not reliable, this is a country setting with slow connections. Please communicate with me regarding pets before booking.

Apr. 19 – 26

$144 CAD per night

Guest favourite

Apartment in Albany

4.93 out of 5 average rating, 159 reviews

Sugar River Hideaway

Newly renovated, 3-bedroom vacation home located on the Sugar River in downtown Albany. Albany is a quaint little town with a lot to offer. Enjoy tubing/canoeing down the river, a diner, pizza place, Italian restaurant, 3 taverns, and a bowling alley all within the downtown block. With being only 30 miles away from Madison and 17 miles from New Glarus, Albany is a prime location for your stay!

Feb. 3 – 10

$169 CAD per night

Guest favourite

Guest suite in Madison

4.96 out of 5 average rating, 181 reviews

Private garden level flat in brand new house

Relax in your Madison home base with a cozy and cute living/dining/kitchenette space, two good-size bedrooms, a full bath and free laundry. Dogs are welcome! Within a 4-block radius you will find a full-service grocery store, several parks, two beaches, and many bars, restaurants, coffee shops and stores. It's a 15-minute walk to Capitol Square and Madison's amazing Saturday farmer's market.

Jul. 22 – 29

$613 CAD per night