26 Hayward Holiday Rentals

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Compare Hayward holiday rentals from 5 rental sites including HomeAway, Booking.com, TripAdvisor and more, ranging from $50 to $795 a night.
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Information about Hayward

About Hayward

A former lumbering town, the Sawyer County city keeps its unique past alive by hosting the Lumberjack World Championships each summer as well as playing host to fishing enthusiasts who have deemed it the home of the Freshwater Fishing Hall of Fame. The region is also known as the “Golf Capital of Wisconsin,” offering almost twenty courses within an hour’s drive.

There is plenty to do in and around the Hayward Lakes area, which has been a Northwoods vacation destination for generations upon end. Year after year, vacationers head over to enjoy fishing, swimming, and quaint small town shops that have everything from freshly made fudge to colorful pairs of handmade moccasins. What’s more is that the Hayward/Cable area plays host to two of the world’s top racing events each year – the American Birkebeiner cross country ski races in February and the Chequamegon Fat Tire bicycle races in September. Get ready to have some fun.

Things to Do in Hayward

There’s no better time to explore one of Wisconsin’s most popular vacation and relocation destinations. With miles of trails for riding snowmobiles, ATVs, cross country skiing, hiking, and biking, to numerous crystal clear lakes for water sports and fishing, Hayward is oozing with activities to take part in all year-round. There are also quite an array of golf courses that’ll provide heaven on earth for any golf enthusiasts, as well as popular local events such as the famous “Friday Night Fish Fry,” which is served weekly at area restaurants. Make sure to check out the Fresh Water Fishing Hall of Fame and Museum to witness the town’s jaw-dropping 143-foot-long, 41-foot-tall musky along with other fishing memorabilia.

Shoppers will adore the adventures to be had within the Hayward Area’s thriving and unique retail community, which has everything from one-of-a-kind specialty and boutique shops such as Backroads Coffee & Tea, Art Beat of Hayward, Tremblay’s Sweet Shop, Hi Ho Silver, Hookstone Winery, and Lynne Marie’s Candies, to multiplex stores such as the Northern Lakes Cooperative and retail chains like Glik’s, Maurices, and L&M Fleet Supply.

Hayward Day Trips

Let’s just say that more than anything else, people travel to Hayward to hang out on the lakes and in the forests. The entire region boasts a tons of luxurious inns, an impressive collection of shops, as well as numerous spots to do wine tastings and to sample locally made microbrews at. Over the years, the Hayward area has grown from a blue-collar resort town into a truly sophisticated place, especially as nearby towns such as Anderson, Bass Lake, Frog Creek, Hunter, Lenroot, Round Lake, Sand Lake, Springbrook, and Stone Lake offer fun day trips for travelers to take as well.

Try out the Apostle Islands Cruise Service or Madeline Island Ferry Line on Lake Superior, or head on down to the Musky Capital of the World for their annual Musky Jamboree Arts & Crafts Fair and Antique Auto Show in August. Other ideas might be to take the gorgeous views from Cathedral Point on Trout Lake, or to see the Snowmobile Capital of the World. You can even attend Cranberry Fest in nearby Eagle River! Back in town, the city itself even hosts the Hayward Library Fall Bike Tour each autumn and the Hayward Fall Festival, where you’ll find arts, crafts, food, brews, wine gardens, live music, sidewalk sales, farmers markets, children's games, trail runs, and a Harvest Baking and Scarecrow Contest. Fun times.

Hayward Accommodations

Whether you’re ready for a summer celebration in the Hayward area or are coming for winter sports, there are a ton of lodging choices to be found. Try out Forest Moon B&B or Grand Pines Resort & Motel, which offers cabin rentals with beautiful rustic interiors, as well as motel and suite options.

Lenroot Lodge, Sawmill Saloon, and Mooselips Java Joint provide first rate accommodations to those hoping to enjoy all Wisconsin has to offer while Pine Villas of Hayward allows you to experience the pure comforts of home along with the adventures of lakes, golf, and quaint downtown Hayward nearby! Be sure also to check out The McCormick House, a block from downtown, the Hollyberry Inn B&B, or the handsomely restored 1923 Spider Lake Lodge, half an hour east of town.

Hayward Transportation

Just about two and a half hours northeast of the Twin Cities and a little under five hours north of Madison, Hayward is easy to get to and around. Try out the NWT Express Shuttle, which offers scheduled and charter service between the surrounding Hayward Area and the Minneapolis/St.Paul International Airport, Mall of America, and everywhere in between. There’s also the option of arriving on a ferry, or rolling along on one of the various local highways or back roads.

Find more information about all things transportation related by using the Department of Transportation's 511 Traveler Information System to keep up-to-date on the latest road construction projects and winter road conditions.

Vacation Rentals in Hayward

Find the best Hayward vacation rentals with Tripping.com. Choose from 93 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $50 a night to $795 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 52 of homes in Hayward offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 1 rentals with pool or jacuzzi, or relax with the family in one of the 82 homes with cable TV.

For all those dog lovers and cat lovers, Hayward offers 31 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 5 rental sites in Hayward where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 60 HomeAway rentals, 14 Booking.com short term rentals and 14 TripAdvisor vacation rentals.
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