House holiday rentals in Madison

4.92 out of 5 average rating, 118 reviews

Lake Geneva cottage with private beach access

This cute cottage for 6 is located just down the street from beautiful Lake Como that offers fishing, boating, and water sports. It is also just a short drive to Lake Geneva and all that it has to offer with its beautiful lake, shopping, historic buildings, and delicious restaurants. Along with the house you get access to the HOA covered private beaches and playgrounds nearby. There is also a bar and grill down the street with live music. Bring your family or your friends and welcome to my home.

4.99 out of 5 average rating, 192 reviews

Home in Galena

The Downtown House - 1820s home steps from Main St

Just steps from Main Street in downtown Galena, this beautifully rehabbed 1820s vacation rental home sleeps up to 7 people. There is 1 reserved parking spot. The kitchen is fully stocked with pots & pans, dishes, toaster, standard coffee maker (coffee/cream provided) and more! There is a washer/dryer with detergent for own your personal use. Don't worry about washing the sheets and towels. That's my job :) Enjoy high speed WiFi, board games, stereo system and streaming-ready/smart 55" TV.

Superhost

Home in Merrimac

4.9 out of 5 average rating, 105 reviews

Lakefront A-Frame | Stunning Views | Private Dock

Escape to our A-frame lake house on a private double lot on Lake WI! What You’ll Love: ✅ Wall of windows – floods the home with natural light ✅ Private dock – great for fishing, swimming & boating ✅ 2 wood-burning fireplaces – cozy up after outdoor fun ✅ Game area w/ pool table – family-friendly entertainment ✅ Secluded & peaceful – enjoy nature in total privacy Prime Location: 🚗 15 min → Devil’s Head Ski Resort 🎿 🚗 20 min → Devil’s Lake State Park 🏞️ 🚗 45 min → Madison & WI Dells 🌆

4.98 out of 5 average rating, 178 reviews

Home in Freeport

Willow Lake Getaway Cozy for 2 - or large families

Beautiful 4 bedroom private lakefront home, cozy enough for 2, large enough for family gatherings for holiday/wk end escape/vacations. Hot tub for cool eves October-April. Extensive private decks with BBQ, outdoor dining & circular daybed with umbrella. 2 docks, 2 SUP boards, paddle boat, 2 kayaks, pingpong table, books and board games. 2 Master Suites with smart tv with private balcony & seating area. fire pit located next to 1st dock. Couples get a 10% discount, message me for details.

4.98 out of 5 average rating, 145 reviews

Updated luxury country getaway short walk to lake!

Luxury getaway close to private beaches, downtown Lake Geneva, and many area amenities. Relax in comfort in this newly renovated 3-bedroom. Enjoy all that the Lake Geneva area has to offer while unwinding in a modern, comfortable retreat. Conveniently located a 3-min walk to Lake Como and a 10-min drive to downtown Lake Geneva. Charming golf cart community with so much to do. Perfect for couples, families, and business travelers. Ideal space for up to 4 adults and great for families of 5.

4.98 out of 5 average rating, 146 reviews

Home in Elkhorn

Red Lodge - Game Room, Hot Tub, Near Lake

Looking for a memorable Wisconsin vacation experience? The Red Lodge is the ideal blend of comfort and style. Super clean, fully stocked, with gorgeous outdoor green spaces and unique amenities, you'll love it here! Jeff - "The devil is in the details, and no detail is overlooked here." Kelsey - "We are obsessed! This is THE nicest Airbnb we've stayed in across the country.. There was something truly unique about each room." Alia - "Hands down the best Airbnb we have ever stayed in."

4.92 out of 5 average rating, 159 reviews

Home in Galena

DunPuttin Place

Nestled on a secluded hillside that overlooks miles of Galena Territory's wildlife preserve, DunPuttin Place offers its guests total privacy, yet the convenience of being only minutes from the area's many popular amenities. DunPuttin Place is not just another carbon copy resort rental. It is a unique private home that has many features seldom found in vacation rentals. It has been tastefully designed and decorated to comfortably accommodate up to 12 guests of all ages.

4.98 out of 5 average rating, 327 reviews

NEW RENO Blue Bungalow DT Lake Geneva Walk to Lake

New listing! Newly renovated 2 bedroom house located in beautiful downtown Lake Geneva. A great choice for a couple or a small family. Perfect location for everything you need in Lake Geneva, but in a very quiet neighborhood setting only 5 blocks away from restaurants, shopping, the beach and the lake. Quick Trip right around the corner for gas, beverages and quick food pick up. FREE on site parking. Coffee bar. On site FREE laundry. Full stocked kitchen.

4.99 out of 5 average rating, 107 reviews

Home in Union Center

Charming country home - great vacation area.

This attractive, peaceful country home is nearby to many family tourist attractions: including Wisconsin Dells, Lake Redstone Park, Elroy-Sparta Bike Trail, fishing, hiking, and canoeing. Provisions for a simple country breakfast are included in your stay. This newly remodeled home with a 2 story layout provides plenty of room for up to 7 guests. Large backyard includes a firepit, as well as a view of the adjacent golf course. Large driveway to park in.

4.88 out of 5 average rating, 147 reviews

Home in McFarland

Lovely Waterfront Two Bedroom House

Lovely two bedroom, one bath in a rural residential area of McFarland on inlet that connects to Yahara River and Lake Kegonsa (house is not directly on lake or river). The home is situated next to a charming campground and marina in nature. Walkable fishing areas. Lake Kegonsa State Park Trail is nearby for walking or snowshoeing. Just a 20 minute drive to downtown Madison! NO PARTIES. You will be asked to leave if there is any party activity seen.

4.97 out of 5 average rating, 155 reviews

NEW! Cozy Downtown Farmhouse, 5BR 3 BA Sleeps 15!!

Our gorgeous home is set in the heart of downtown Lake Geneva. 5 bedroom, 3 bathroom home that is two blocks from the lake and a few blocks from downtown shopping and restaurants. We just completed an extensive renovation of the home and it is now ready for you to stay for your dream vacation. Our homes are fully licensed and legal for short term rentals. We also rent the home two doors down and another in nearby Williams Bay!