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Top Wisconsin Winter Getaways

Wisconsin, while typically not considered as "northern" as it's neighbor Minnesota, nonetheless boasts some of the best wintertime activities in the country. From hockey to sledding to snowmobiling, a day outside in a Wisconsin winter is a day of pure entertainment. And while you're living it up outside, why not stay somewhere that will make you just as excited to get back inside? These are the best of the best, the creme de la creme, Los Mejores of Wisconsin's winter resorts. If you don't spend some time in the cold months with these guys, you're doing yourself a disservice.
1

Tri Lake Timbers Resort & Gardens

Iron River, Wisconsin

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+1 (866) 845 - 1345
Make Tri Lake Timbers Resort & Gardens your basecamp when you visit the Iron River Area during the winter. This Northern Wisconsin snowy destination features a primer snowmobile playground.Explore hundreds of... read more

Make Tri Lake Timbers Resort & Gardens your basecamp when you visit the Iron River Area during the winter. This Northern Wisconsin snowy destination features a primer snowmobile playground.

Explore hundreds of miles of wilderness trails and natural beauty. The Iron River features plenty of options to choose from and you are guaranteed to find the best that fits your needs. For instance, trail 63 travels from Hayward north through Cable, Drummond and Grandview. While trail 7 features a scenic view of Lake Namakagon and trail 8 provides an excellent opportunity to spot wildlife at the Rock Lake Semi-Primitive Area. No matter which one you decide to explore, Iron River provides excellent tours. And after an adrenaline rush, your cozy cabin awaits at Tri Lake Timbers Resort & Gardens. Indulge and rejuvenate in amenities like fireplaces, full kitchens, and cable television. Winter enthusiasts return year after year and you can as well enjoy this destination every year!

Address

69210 E Long Lake Rd Iron River, WI 54847-3408 US

Highlights

Located minutes from Long Lake, Tri Lake Timbers Resort & Gardens offers a great opportunity to cast your line even during the winter time! Walleye, bass, and northern pike are waiting for you!

Related activities

Whether you hunt with bow or rifle, over bait or with dogs, there's plenty in the area for the avid hunter. Experience Wisconsin's North Woods first hand- you may be surprised by what they have in store for you! You'll find grouse, pheasant, Woodcock, and plenty of deer in the area. Just don't forget your orange clothing!

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2

Northernaire Resort

Three Lakes, Wisconsin

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+1 (877) 801 - 9870
Northernaire Resort would seem to be more of a summer paradise than a winter one, as it’s situated on the largest chain of inland lakes in the world. And yes, in the summer those 28 lakes make for some fantastic... read more

Northernaire Resort would seem to be more of a summer paradise than a winter one, as it’s situated on the largest chain of inland lakes in the world. And yes, in the summer those 28 lakes make for some fantastic fun. But winter at Northernaire is just as, if not more, memorable than the summer.

Condos, cabins, and vacation homes are all available for you to peruse, and each are exceedingly cozy, so as to best protect you from winter’s sharp bite. But when you bundle up and get outside, Northernaire does not disappoint. Skiing, snowshoeing, and snowmobiling are all available if you’d like a physical challenge. If you’d prefer to just enjoy the serene snowy beauty of Three Lakes, hop into a horse-drawn carriage for an old-fashioned sleigh ride. Then go warm up in the indoor pool and hot tub, hit the hay, then wake up and do it all again!

Address

6990 Bengs Rd, Three Lakes, WI 54562

Highlights

The highest point in WI is Timms Hill, measuring 1,952 feet above sea level.

Fun facts

Wisconsin's state nickname is the Badger State!

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3

Glidden Lodge Beach Resort

Sturgeon Bay, Wisconsin

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+1 (866) 813 - 2765
Experience the beauty of the winter season at Glidden Lodge Beach Resort in Sturgeon Bay, Wisconsin.This beachfront inn is located on the Wisconsin shores of Lake Michigan just a short drive from downtown Sturgeon... read more

Experience the beauty of the winter season at Glidden Lodge Beach Resort in Sturgeon Bay, Wisconsin.

This beachfront inn is located on the Wisconsin shores of Lake Michigan just a short drive from downtown Sturgeon Bay on the “Quiet Side” of Door County. Glidden is about two miles south of Whitefish Dunes State Park with its many hiking and ski trails to enjoy during the winter and every other season! The resort features luxurious one, two, and three bedroom condo rental units that all feature a breathtaking view of Door County’s Lake Michigan. A gas fireplace, whirlpool tub for two, fully appointed kitchen and private patio or deck are standard features. Enjoy a soak in the on-site hot tub, sweat it out in the sauna, or fulfill your exercise regime in their fitness center.

Address

4676 Glidden Drive Sturgeon Bay, Wisconsin 54235

Highlights

There are a total of 31 beautiful one, two, and three bedroom condo rentals!

Related activities

The resort is only a short drive from Sturgeon Bay and the other picturesque Door County villages.

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4

Sand County Service Company

Lake Delton, Wisconsin

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+1 (800) 822 - 7768
Sometimes it’s just too dang cold to go outside for some winter activities. If you’re on a trip to a regular resort, you’re forced to remain cooped up until either the weather is more cooperative or you leave.... read more

Sometimes it’s just too dang cold to go outside for some winter activities. If you’re on a trip to a regular resort, you’re forced to remain cooped up until either the weather is more cooperative or you leave. As they say in most infomercials, “There has to be a better way!”

Never fear! Sand County Service Company provides that way, with fantastic accommodations and a close proximity to the entirely-indoor Wisconsin Dells. With dozens of restaurants, night spots, attractions, and shopping, you’ll never lack for a fun indoor diversion on a terrible weather day. Obviously, the real attraction to the Dells are the incredible water parks. Your family will absolutely flip when they go from freezing outside to zooming down a slide and jumping in a hot tub. Spend your days at the Dells and your nights with SCSC.

Address

116 W Munroe Ave, Wisconsin Dells, WI 53965

Highlights

The state bird is the American Robin!

Fun facts

The state beverage of Wisconsin is milk!

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5

Lakewoods Resort

Cable, Wisconsin

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+1 (833) 527 - 0967
Lakewoods Resort is a winter lover's paradise. There is enough to do you may not get to it all in your visit!The resort sits on the shores of Lake Namakogon, perched in Northern Wisconsin. When it comes to the snow,... read more

Lakewoods Resort is a winter lover's paradise. There is enough to do you may not get to it all in your visit!

The resort sits on the shores of Lake Namakogon, perched in Northern Wisconsin. When it comes to the snow, there are few destinations that can compete with Lakewoods. Featuring over 600 miles of groomed trails in Bayfield County, and Sawyer County and Hayward Lakes adding another 600, snowmobilers will not likely run out of trails during their trip. Cross country skiing, ice-skating, and ice fishing on Lake Namakagon are few other activities you could partake in before heading back to your accommodation to warm up for the night. With less traffic and lower rates than the summer, it is a no-brainer to take a winter trip up north.

Address

21540 County Road M Cable, Wisconsin 54821

Fun facts

They are most notoriously known as a snowmobiling destination, being voted the number one snowmobile resort in the the country six times by SnowGoer Magazine.

Related Onsite Offerings

Lakewoods also has the Lakeside Restaurant. But if you are in the mood to cook yourself, the resort offers a unique service in which they will prepare ingredients for you to carry out and make on your own.

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6

Harbor Shores on Lake Geneva

Lake Geneva, Wisconsin

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+1 (866) 302 - 4267
Located in the heart of buzzing downtown Lake Geneva, Harbor Shores on Lake Geneva puts you within footsteps of fun-filled winter activities and city attractions. When you're not exploring, rejuvenate onsite with a... read more

Located in the heart of buzzing downtown Lake Geneva, Harbor Shores on Lake Geneva puts you within footsteps of fun-filled winter activities and city attractions. When you're not exploring, rejuvenate onsite with a host of welcoming amenities and well-appointed rooms.

Harbor Shores on Lake Geneva is teeming with winter adventures. Visit the breathtaking Ice Castles in Lake Geneva and witness LED-lit sculptures, frozen thrones, fountains, and more! If you’re looking for some more adventure, head over to Wilmot Mountain for some epic downhill skiing, snowboarding, and tubing. The distinctly different rooms at Habor Shores all offer a unique experience and combine panoramic lake views and panoramic views to create the ultimate Lake Geneva experience. Breathe in the fresh Wisconsin air on your private balcony, grab a drink from the wet bar, and munch on complimentary breakfast each morning. Choose between the sparkling lake and lush park views when you stay at this centrally located gem. You're truly in the middle of it all at Harbor Shores on Lake Geneva!

Address

300 Wrigley Drive, Lake Geneva, WI 53147

Related activities

Pack a family picnic and head over to Lake Geneva’s Seminary Park, which is just behind the resort's property.

Related Onsite Offerings

Gino’s East Restaurant and Bar serves up scrumptious lunch and dinner, heated pools provide the fun, and the sauna serves as the perfect place to unwind!

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7

The Beacons of Minocqua

Minocqua, Wisconsin

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+1 (866) 339 - 1835
Cozy condos, cabins, and cottages as far as the eye can see! The Beacons beckons, because it’s the best. Your friends and family will feel fantastic!Alliteration aside, The Beacons is packed to the gills with... read more

Cozy condos, cabins, and cottages as far as the eye can see! The Beacons beckons, because it’s the best. Your friends and family will feel fantastic!

Alliteration aside, The Beacons is packed to the gills with everything a winter getaway could require. It offers condos, cabins, and cottages, and offers you the choice of whichever you believes fits the best. If you’re a bigger party, the incredible luxurious cottage might be for you, while if it’s a romantic getaway, mayhaps the snugness of the condos catches your eye. Whichever you pick, each are northwoods retreats filled with all the comforts of home, from full kitchens and fieldstone fireplaces to spacious bedrooms and baths. Go out for some fun in the snow, then come back in and warm up next to the fire with a mug of hot cocoa. Sounds like a perfect getaway to us.

Address

8250 Northern Rd, Minocqua, WI 54548

Related activities

The resort is only 1.7 miles from both the Hiawatha Trail and Bearskin State Park Trail.

Fun facts

There are 72 counties in Wisconsin.

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+1 (866) 452 - 9565
Get away to the Waterbury Inn for a quaint country setting in a bonafide winter wonderland!Settle into a comfy multi-bed lodging suite and familiarize yourself with the fully equipped kitchen, living and dining... read more

Get away to the Waterbury Inn for a quaint country setting in a bonafide winter wonderland!

Settle into a comfy multi-bed lodging suite and familiarize yourself with the fully equipped kitchen, living and dining rooms, then kick your feet up and relax with the flat screen TV, and free wireless internet. Outside, you have the world of Wisconsin winter activities open to you! Some of the most popular activities are sleigh rides, ice skating, and simply taking a walk in one of the nearby state parks. The absolute serenity of forested rural Wisconsin is, after all, unparalleled.

Address

10321 N Water St, Sister Bay, WI 54234

Population

Wisconsin had 5,742,713 residents as of 2013.

Fun facts

Wisconsin is the 20th most populous state in the US.

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9

Cliffside Resort & Suites

Wisconsin Dells, Wisconsin

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+1 (866) 940 - 1109
Cliffside Resorts & Suites is an excellent four-season family vacation destination that lends itself to an unforgettable winter getaway.Ideally situated on Lake Delton's shores amid nature's bounty and seemingly... read more

Cliffside Resorts & Suites is an excellent four-season family vacation destination that lends itself to an unforgettable winter getaway.

Ideally situated on Lake Delton's shores amid nature's bounty and seemingly endless outdoor recreation, Cliffside Resort & Suites is your basecamp for a Wisconsin winter retreat. Their common laundry area ensures you'll be able to wash all of those layers, and the game room is perfect for those days that are just too cold to go outside. Their fitness room is an excellent amenity for anyone needing to stay in shape while on vacation.

Address

351 Canyon Road Wisconsin Dells, Wisconsin 53965

Extra Stops

Be sure to check out Mirror Lake State Park for cross country skiing and snowshoeing.

Related activities

From cross-country skiing to snowmobiling, there are many winter sports opportunities available just minutes from Cliffside Resort & Suites.

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+1 (715) 466 - 6300
Heartwood Conference Center & Retreat has everything you could possible want from a Wisconsin winter getaway, and a whole lot more!Heartwood believes that perhaps their most inviting characteristics is their... read more

Heartwood Conference Center & Retreat has everything you could possible want from a Wisconsin winter getaway, and a whole lot more!

Heartwood believes that perhaps their most inviting characteristics is their range of accommodations to match each guest’s specific needs. The comfortable Eagle Lodge Guest Rooms are supremely cozy and feature amenities that any traveler will appreciate. Meanwhile, the Duplex Cabins are suited for larger groups, be it family or social. And, “for a truly authentic lakeside getaway”, choose Heartwood’s coveted cottages, filled with charm and the warmth you’ll sorely need on a cold winter night. Outside of your accommodations, enjoy cross-country skiing, snowshoeing, tubing, broomball, ice skating, and snowmobiling!

Address

N10884 Hoinville Rd, Trego, WI 54888

Highlights

The state domestic animal is the dairy cow!

Fun facts

The state insect is the honey bee!

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11

Woodside Cottages of Bayfield

Bayfield, Wisconsin

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+1 (715) 779 - 5600
If your family is looking for a secluded retreat to relax and enjoy winter in a toasty retreat, then Woodside Cottages of Bayfield is the perfect vacation location for you.Sitting on eight densely wooded acres of... read more

If your family is looking for a secluded retreat to relax and enjoy winter in a toasty retreat, then Woodside Cottages of Bayfield is the perfect vacation location for you.

Sitting on eight densely wooded acres of the Lake Superior shoreline, Woodside Cottages of Bayfield provides a cozy and unique location for your family to reconnect. Bayfield is known as the gateway to the apostle islands and is a great place to visit no matter the season. The natural beauty of this area is paralleled in few other places in Wisconsin. The resort itself features 13 recently built high quality cabins constructed to have your family feeling right at home. Families will love the list of amenities that include plenty of spaces to stretch out, Jacuzzis, AC, full kitchen for easy meal preparation, gas fireplaces and porches to relax and observe the lush wilderness. The area has activities to offer visitors of all ages. Your family will enjoy nature hikes, bike rides, fishing on Lake Superior, kayaking, boating, relaxing on the beach or in the winter skiing, snowshoeing and snowmobiling are popular. The Bayfield community and surrounding area has events that are fun such as Bayfield Apple Festival, Festival of the Arts, Sailboat Races, Fourth of July, Blues Fest and so much more. Get in touch with the friendly and knowledgeable customer service to begin your family's next unforgettable Wisconsin adventure.

Address

Woodside Cottages of Bayfield 84790 Hwy 13 Bayfield, Wisconsin 54814

Related activities

Fans of golf will also like staying in Bayfield. The Apostle Highlands Golf Course is not far from the resort. This course is great for all skill levels and the surrounding views will absolutely enhance the overall golf experience.

Related Onsite Offerings

The resort has plenty of things for families to enjoy on-site including five acres of open space, fire pits, grills, tables, furniture and outdoor games.

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12

The Cove of Lake Geneva

Lake Geneva, Wisconsin

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+1 (800) 770 - 7107
Ideal for both family vacations and romantic escapes, the Cove of Lake Geneva is southeastern Wisconsin's premier all-suite resort!With private balconies, patios, a whirlpool, fireplace and two 32" flat-screen... read more

Ideal for both family vacations and romantic escapes, the Cove of Lake Geneva is southeastern Wisconsin's premier all-suite resort!

With private balconies, patios, a whirlpool, fireplace and two 32" flat-screen televisions, each room here will make you dubious of leaving. While the accommodations are certainly impeccable, you'll want to spend as much time as possible exploring the superb winter wonderland that is the Lake Geneva area! Make a snow angel outside, visit some of the charming shops and festivals in town, or snowmobile along one of the dozens of nearby paths! Afterwards, return for a soak in the hot tub or take a well-deserved nap!

Address

111 Center St., Lake Geneva, WI 53147

Highlights

The Cove of Lake Geneva can also function as a conference center. Leave the hassle of drawing creative seating arrangements aside and let The Cove assist in tailoring your event or gathering with more than 6,000 square feet of meeting space that can accommodate up to 300 guests.

Related Onsite Offerings

Treat your tastebuds to something delicious throughout your stay at the Cove of Lake Geneva. Their Cove Café & Lounge offers invigorating Colectivo Coffee and light breakfast items, perfect for starting your day. The Sprecher’s Restaurant & Pub is the ideal place to unwind after fun with an incredible lunch or dinner!

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13

Serenity Bay Resort

St. Germain, Wisconsin

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+1 (715) 479 - 8866
Choose from two or three bedroom Lakeside Cabins right on the beach or three bedroom Lakeview Townhomes just a short walk from the beach, and enjoy the gorgeous fall colors at Serenity Bay Resort!If skiing or... read more

Choose from two or three bedroom Lakeside Cabins right on the beach or three bedroom Lakeview Townhomes just a short walk from the beach, and enjoy the gorgeous fall colors at Serenity Bay Resort!

If skiing or snowmobiling is your game, you've come to the right place! After you've settled into your superbly cozy cabin, head outside and participate in one or both of these popular wintertime activities! The high quality trails and beautiful scenery of St. Germain features over 100 miles of snowmobile trails connected to neighboring communities throughout the Northwoods. Meanwhile, downhill skiing in Michigan's Upper Peninsula is only an hour away. If you prefer flat ground, go cross country skiing, snowshoeing or ice skating close to home. Finally, if the weather is uncooperative, head out to enjoy the shopping in Minocqua, Eagle River, Sayner or Boulder Junction- perhaps buy a souvenir to remember a fantastic experience at Serenity Bay Resort!

Address

1276 Halberstadt Rd, St Germain, WI 54558

Highlights

Beautiful Little St. Germain Lake is one of the finest producing lakes in northern Wisconsin covering 959 acres with 15 miles of shoreline.

Related activities

Nearby go karts, horseback riding, wildlife parks, kayaking, canoeing and more are sure to please the family!

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14

The Conger Collection

Eagle River, Wisconsin

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+1 (612) 308 - 6434
If you’re looking for the utmost in winter getaway luxury, look no further than the Conger Collection. Specializing at creating the very best experience for you and your guests, Conger will take care of the little... read more

If you’re looking for the utmost in winter getaway luxury, look no further than the Conger Collection. Specializing at creating the very best experience for you and your guests, Conger will take care of the little things so you’re free to focus on having the best vacation you possibly can.

If you’ve ever had a bad experience at a mega resort, you know the feeling of being ignored and not valued by the people you’re entrusting to facilitate a great vacation. Conger is here to bring the hospitality back to the luxury vacation rental, and the do it with style. Anything, absolutely anything, can be taken care of if you but ask . Refrigerator stocked prior to your arrival? No Reservations for a good restaurant?A boat gassed up waiting for you at the dock? Tips on fishing or guide services? All will be happily attended to. From arranging private jet service to recreational vehicle rentals, a stay with Conger is a stay with first-class service.

Address

1714 Bellewood Dr, Waunakee, WI 53597

Total area

Wisconsin is 65,503 square miles.

Fun facts

Wisconsin is the 23rd biggest state in the USA.

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15

Westwood Shores Waterfront Resort

Sturgeon Bay, Wisconsin

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+1 (800) 440 - 4057
While the name sounds like it’s more likely to be in coastal California, Westwood Shores Waterfront Resort is actually a dynamite resort located in beautiful Sturgeon Bay, Wisconsin. Breathtaking views and... read more

While the name sounds like it’s more likely to be in coastal California, Westwood Shores Waterfront Resort is actually a dynamite resort located in beautiful Sturgeon Bay, Wisconsin. Breathtaking views and luxurious rooms all at an affordable price, you won’t regret spending a winter getaway at Westwood.

Each of the resort’s 38 suites features a breathtaking sunset view of the bay, modern amenities, and incredibly comfortable upholstery. If the cold is too much for you relax indoors in the heated pool, whirlpool, and sauna. Otherwise, get out there! Westwood Shores also has a wide variety of winter activities available, from snowmobiling, snowshoeing, and cross-country skiing to horse drawn sleigh rides and tubing. Whether you’re with your family or significant other, Westwood has a snowy activity that will be to your liking.

Address

4303 Bay Shore Dr, Sturgeon Bay, WI 54235

Highlights

Wisconsin became a state on May 29,1848.

Fun facts

Soem of the major industries of Wisconsin are dairy products, corn, paper, and beer!

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16

Holiday Acres

Rhinelander, Wisconsin

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+1 (800) 261 - 1500
It just makes sense to head to Holiday Acres during the Holiday season- don't argue with logic!Set against the shores of beautiful Lake Thompson, Holiday Acre's vast acres of natural paradise are a superb place to... read more

It just makes sense to head to Holiday Acres during the Holiday season- don't argue with logic!

Set against the shores of beautiful Lake Thompson, Holiday Acre's vast acres of natural paradise are a superb place to enjoy the winter months. While snowshoeing, bird-watching, and skating are all fine ways to spend a frigid afternoon, the Rhinelander Area is most known for its incredible snowmobiling. There are more than 1,000 miles of trails running throughout Oneida County, which link to thousands more miles of trails throughout northern Wisconsin and Michigan’s Upper Peninsula. Just ask Holiday Acres' friendly staff and they'll point you in the right direction. If you're looking for adventure, it's easy to find here!

Address

1762 Oakdale Ave, West St Paul, MN 55118

Highlights

Rhinelander's mascot is the Hodag, a mythical beast that is said to have the head of a frog, the face of an elephant, stout legs, a spiky, dinosaur-like back and a long tail.

Fun facts

Local snowmobile clubs like the Hodag Sno-Trails groom regularly throughout the winter, resulting in a superior experience for all riders!

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17

Edgewater Inn & Cottages

Eagle River, Wisconsin

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+1 (715) 479 - 4011
Few things compare to a crackling fire in a rustic cottage while snow falls gently to the earth outside. It just oozes coziness. Stop imagining and start living it at Edgewater Inn & Cottages!Even if they lacked... read more

Few things compare to a crackling fire in a rustic cottage while snow falls gently to the earth outside. It just oozes coziness. Stop imagining and start living it at Edgewater Inn & Cottages!

Even if they lacked their incredibly comfortable cottages, there would still be plenty of reasons to visit Edgewater in the colder months. The area is rife with cross-country skiing, snowshoeing, and snowmobiling trails, for any skill level. Meanwhile, all cottages feature at least a full size bed in each bedroom, cable TV, a kitchen (with full size refrigerator, stove, dinette table, microwave and coffee maker), outdoor charcoal grill, and use of rowboat (if the lake hasn't frozen over yet). Settle in and get comfortable, cause it's cold outside!

Address

5054 WI-70, Eagle River, WI 54521

Related activities

The inn is only 11 miles from Anvil Lake Trail State Natural Area.

Related Onsite Offerings

Additional perks include a business center and meeting space, as well as free parking for cars, trucks and trailers.

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View call direct
+1 (800) 472 - 6670
This Wisconsin getaway is the third largest in the Midwest with 300 acres of skiable terrain, 500 vertical feet of day and night runs, 100% snowmaking and nine lifts. What more could you want from a winter... read more

This Wisconsin getaway is the third largest in the Midwest with 300 acres of skiable terrain, 500 vertical feet of day and night runs, 100% snowmaking and nine lifts. What more could you want from a winter destination!

As one of the Midwest's 10 Best Ski Resorts, Devil's Head Resort & Convention Center features a host of amenities and accommodations to enthrall you and your family. The 3,000-foot top-to-bottom Terrain Park lets you take your skiing adventure to the next level, while beginners will enjoy the Ski & Ride School, which guides you through steps to ski or snowboard like a pro. And to make it even easier to have fun, Devil's Head Resort offers ski-in/ski-out accommodations that put you right beside the beautiful snow-covered slopes. Their lodging comes in a variety of styles including comfortable lodge rooms to spacious condominiums at Glacier Ridge which are equipped with kitchens, gas fireplaces and more. What more could you want? Absolutely nothing!

Address

S6330 Bluff Road Merrimac, WI 53561

Highlights

Don't worry about lugging all your winter equipment with you on your vacation. Devil's Head offers a luxury Ski Pro Shop and Gear Rentals right onsite to take all the hassle out of getting ready for your adventure.

Related Onsite Offerings

The resort offers free hourly or overnight ski and snowboard storage in the lower level of the Cliffhaus adjacent to the snowboard rental area.

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