Holiday houses in Little Round Lake

Diamonds On The Water on Lac Courte Oreilles

If you’re looking for your next getaway this is it! You will be quite hard-pressed to find a place closer to the water! This gorgeous Northwoods property sits on almost a 1⁄2 acre lot on the beautiful Lac Courte Oreilles lake with 260 feet of frontage. Wake up to incredible lake views from your main living area and bedrooms. The four season home features hardwood floors, hickory cabinets, beautiful custom tiled shower and an amazing peninsula location! AND, it is right on ATV/Snowmobile trail!

Lakeside Cabin Retreat on Quiet Peninsula

Avoid crowded resorts and immerse yourself in nature at this private, secluded and peaceful lake cabin. Osprey Lake is quiet and clear and known for great fishing all year. This location offers the option to simply relax and watch for loons, otters, hummingbirds, and the occasional black bear, or to be adventurous and paddle through a beautiful channel to Little Round Lake and Round Lake. Nearby amenities include a variety of trails, restaurants, a casino, and all the charm Hayward has to offer.

Evergreen Escape - cozy cabin near Grindstone Lake

Welcome to Evergreen Escape! Located between Grindstone Lake and Lac Courte Oreilles, our cabin is the perfect base for your Hayward getaway. Enjoy fishing, boating, and swimming on nearby lakes, or hit the CAMBA trails, ATV/snowmobile routes, and golf courses like Big Fish and Hayward Golf Club. Try your luck at Sevenwinds Casino or explore the town’s shops, breweries, and the famous Fishing Hall of Fame. Whether you’re after outdoor adventure or cozy cabin vibes, Hayward has something for you.

The Seeley Hills Chalet near iconic "OO" Trailhead

A Nordic-meets-Northwoods trail sports chalet on 3 wooded acres, just off the main path between Hayward + Cable in Seeley, WI. Only 2 miles from the iconic “OO” Trailhead with quick access to the Birkie ski trails, mountain and fat bike trails, gravel roads, UTV trails, & more. This charming chalet - with a wood-fired sauna, large game room, firepit & more - puts you among the pristine woods, water, and all the iconic events, restaurants, shopping, & nightlife of two key Northwoods communities.

The Mill Pond Apartment - .5mi to Downtown Hayward

Views of The Big Musky from the deck! Newly remodeled & spacious studio apartment located .5 mile from Main Street. Enjoy walking to downtown restaurants and shops of downtown, while being a short distance to ski & bike trails. Conveniently located - walk to the Musky Festival, American Birkebeiner, Lumberjack World Championships, & the Cheq 40. Includes a full kitchen with new appliances, king bed, full bathroom, private work area with desk, WiFi, smart TV and private entrance. No kids or pets

Hayward House | Trailers Ok, King Bed, 1mi to Town

The Hayward House is your comfortable home retreat close to downtown Hayward on 2+acres with a spacious living room. ATV right from the house! Plenty of parking for anything - boats, snowmobile & atv trailers. 1 mile to Downtown Hayward. 5 miles from Hatchery Creek for the CAMBA singletrack and Birkie Trail. Less than 1 mile from the start of the Chequamegon 40 and the Birkie Finish Line! Wifi, Smart TV (YouTubeTV, Netflix, Disney+, Amazon), washer & dryer. New heating and central a/c system.

Cabin on Pine Cone Pond

Welcome to our Cabin, your year-round Northwoods retreat! Relax with the whole family in this newly built cabin that is nestled within a peaceful & private wooded community; a tranquil pond surrounded by 28 acres of woodlands. Minutes from Hayward, with convenient access to fishing, ski trails, & biking, hiking, ATV, & snowmobiling trails. Designed with guest comfort in mind, the cabin features a perfect blend of boho-chic furnishings creating a tranquil, cozy & natural yet stylish retreat.

Haakon House

Relax with family and friends at a Northwoods retreat. The cabin is a newer build at the end of a quiet road near the start line for the Prince Haakon cross country ski race. It can accommodate large groups with as many as 12 in the cabin on beds and pull out furniture (plus a bunkhouse). Connect to CAMBA mountain bike and American Birkebeiner Nordic ski trails from the front door, through private trails and the Mosquito Brook trailhead. Enjoy the screen porch and comfortable accommodations!

Sylvan Chalet, Modern, Lakefront, Close to Trails

Built as a winter or summer escape for a couple or small group, this beautiful four season cabin is a great way to experience the Northwoods of Wisconsin in a modern, well-appointed, aesthetically rich space designed with relaxation in mind. Cabin is brand new as of January 2024. Host is 14 year "superhost" This is a default "no pets" cabin, however certain sizes and breeds are allowed by permission only. We have a NEMA 15-40R outlet for level 2 EV charging. You bring chord and adapter

Modern & Cozy Northwoods Cabin w Cedar Hot Tub

We fell in love with Hayward for the same reason so many people do: the lakes, the quiet, the slower pace, and how easy it is to feel connected to nature. The Cabin for Two sits at the end of a private road on a small wilderness lake, surrounded by county forest. Wildlife is part of daily life here. Loons call across the water, swans and other waterfowl pass through, and deer regularly move through the yard. In the warmer months, bears occasionally travel through the area.

Luxury Lakefront Lodge with amazing views

Welcome to paradise! A charming 100 year old lodge with sandy swimming on crystal clear Round Lake! The cabin is very large and great for groups or families. Enjoy free parking, a sandy shoreline, and plenty of room for yard games. A lakeside screen porch and new deck provide commanding lake views. The brand new kitchen is fully equipped. The property is wooded and private, but you’re just minutes away from bars, restaurants, shops, and of course the casino!

Charming Cabin right on Round Lk in Richardson Bay

Rustic, cozy cabin in Richardson Bay on 3,000 acre Round Lake. The cabin porch is about 50 feet from the lake! 2016 21' Bennington 90 HP pontoon included with all summer rentals. Three bedrooms with three queen beds. Two story loft, two bath with Jacuzzi tub in loft, two gas fireplaces, fully furnished 3 season porch, and central air/heating. This cabin lacks nothing for supplies! Just bring your clothes and fun! It is completely furnished!