Vacation Rentals By Owner In Winter, WI

Cozy, clean, well-equipped & fully furnished, 4-season cottage on Lake of the Pines in the heart of the Flambeau River State Forest in Winter, WI. Direct access to ATV/snowmobile trails. Hunt, fish, hike, bike, x-country ski, swim, boat, ATV/snowmobile, or just relax, unplug, and unwind. You can do it all at Pinecone Cottage! Into the forest, I go to lose my mind and find my soul. John MuirbrbrThis is a very remote location, cell phone coverage is unreliable, WIFI is very slow. brbrWalk right from the cottage onto public hunting land.brbrThe lakeside bedroom features a full-size bed, new bedding, blankets, and pillows. brbrThe bunk room features a Full over Full bunk bed rated for 400 pounds on the top bunk. New bedding, pillows, blankets, LED lighting above the lower bunk. brbrThe kitchen is FULLY furnished with everything you need to feel at home. You will find a coffee pot and filters, blender, crockpot, all cooking, baking, and serving equipment and tools to whip up your favorite meals. brbrBath and kitchen towels are provided.brbrLake of the Pines is a 273-acre lake that has residents/resorts on the south-eastern & southwestern shorelines, the Lake of the Pines State Park on the northwest shoreline, & the Flambeau State Forest on the north-eastern shorelines. Fish include Musky, Panfish, Largemouth Bass, & Walleye.brbrDish soap and hand soap are provided. brPet dishes and pet towels provided.br2 kayaks and 2 life jackets providedbr1-row boat included

Pets & kid Friendly ,direct access to ATV& snow trails, private dock

Winter, Wisconsin, United States

Bed

Sleeps

Exceptional(16)

$262.7

Welcome to The Loft @ Moxi Lodge and Lounge... the perfect place to lay your head or enjoy a few craft cocktails or specialty taps in our lakefront lounge!brbrThe lodge is located just a short walk from our private shoreline on Connors Lake. This two-bedroom upper-level unit is the perfect place to unwind and relax after a long day of outdoor fun. We are centrally located in the heart of the Flambeau River State Forest. The forest boasts an astonishing 91,000 acres of public land ready for all of your outdoor recreational activities. Whether you are looking to bag a trophy buck or bass, or love miles of snowmobile/atv and skiing trails... this area has you covered!brbrAll of our units include fully furnished full size kitchens, bed linens, and bath towels/accessories.brbrNot feeling like cooking after an exhausting day outdoors Don't worry, we are just a couple minute drive from two of the Northwoods of Wisconsin's most iconic bar/restaurants!brbrPlease note: br-This is an upper-level unit and requires access via stairs.br-The Loft is reserved for guests a minimum of 10 years old and older br-We have a zero-tolerance guest pet policy. Guests who bring pets on to the property (in the building or otherwise) will be asked to find suitable accommodations for the pet elsewhere or terminate the reservation without refund.

Hotel Resort

The Loft @ Moxi Lodge and Lounge

Winter, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(43)

$406.18

This family friendly log cabin is for those who truly want to avoid the crowds. At the end of a dead-end paved road the property boarders the 90,000 acres of the Flambeau River State Forest. With easy access to miles and miles of snowmobile, ATV, and hiking trails in the heart of Wisconsin Elk country. brbr*Please do not request lodging if you plan to party. Our home is intended for mature/family guests only. Capacity is 8 guests. brbrOur lake is deep and clean and has very little weekday boat traffic. The typical water depth at the end of our dock is 6'. brbrWith two decks, fire pit, 4 kayaks, 2 canoes, a paddle boat, swim deck, and bikes at your disposal. One slip for available for boat, please ask for spot. brbrPerfect for wet feet or snow, the lodge's main floor is carpeted with indoor/outdoor treatments for easy clean-ups and peace of mind. The main floor has master bed (California King), second bed room (queen), bathroom, dinning room, bonus rec room with pullout sofa bed, and family room. brbrOur basement has open utility room, bathroom, sauna, bedroom #1 and #2 with queen and single beds. Additional queen is in common area. So, here's the bed breakdown: Basement: 3 queens, 2 singles, 1 bunkbed, 2 roll-away single. Mainfloor: Cal. King and queen, one pullout sofa. And the bunk loft, suitable for kids has 4 single beds. Fun aye brbr- Dog kennel attached to garage. No more that two housebroken dogs permitted. *Pet fee required.brbrConnors Lake is a 410 acre lake located in Sawyer County. It has a maximum depth of 82 feet. We have a great sandy beach and public boat landing. Fish include Musky, Pike, Panfish, Largemouth Bass, Smallmouth Bass and Walleye. The lake's water is moderately clear.brbrConsideration of our neighbors is paramount. No camping or RVs on property, events, fireworks, loud music or parties. This lodge is designed for mature guests who'll respect the lodge and neighbors. No more than 2 housebroken dogs allowed and all pets must be contained to the property. Should pets impede on our neighboring yards you'll be asked to vacate our property. brbrbrbrbrbrbr

Log cabin on beautiful clear lake perfect for your family retreat.

Winter, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(54)

$589.41

Our gorgeous lodge nestled in the pines boasts an open floorplan with a beautiful 2-story wall of windows looking out onto a large deck with HOT TUB (available June thru Sept only) and stunning views of Hunter Lake. While our permit only allows for 10, this home has 3 bathrooms along with 4 bedrooms providing space for 11 in beds, with additional sleeping for 2 available on large comfy Cordaroy brand beanbag beds in the lower level gathering room. brbrOur large kitchen includes beautiful granite countertops, a breakfast bar with seating for 4 and is fully stocked for your use. The dining area provides seating for 10 and the adjacent screen porch has seating for 8 guests. Plenty of room for your large group! Additionally, there is a 2nd screen porch providing a quiet space of tranquility.brbrSince you're probably coming to enjoy the great outdoors, here are a few other amenities offered:brIn addition to the large furnished deck you will find our fire pit overlooking the lake, a canoe outfitted with a trolling motor, and kayaks (6 adult & 1 child) w/paddles & lifejackets. And new for 2026, we will offer a small Mitey-toon pontoon boat that accommodates 4 adults - perfect for fishing, exploring or anchoring offshore for a swimming platform. brbrWhen winter rolls in, bring your snowmobiles to enjoy miles of Sawyer County trails. Garage and heated shop available for your sleds & gear. Our driveway has a large parking pad for your trailer. There's even a sledding hill for the kiddos. brbrATV trails are also nearby and plentiful! A golf course is across the lake (just a 5-minute drive) and the 3-million acre Chequamegon-Nicolet Nat'l Forest offers hiking, biking, fishing, skiing, foraging or hunting. brbrWe doubt you'll ever feel like leaving, but just in case, the adorable town of Hayward lies just to our west and is a great place to shop, eat and enjoy the local artisan community. The lumberjack show is a must see and we highly recommend a stop at 3 Fly Sisters Taps & Wine on Main Street! brbrWe think you'll find our lodge to be a perfect spot to gather with family and friends! We are eager to welcome you to Hunter Lake...again & again!

Lodge

Hunter Lake Lodge awaits...

Winter, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(5)

$133.64

Welcome to your home away from home! Our one-bedroom, one-bathroom cozy cottage will make you and your guests never want to leave! We wanted the décor to be simple but also implement different patterns on the curtains and furniture to capture the eye.brbrThe kitchen area has plenty of space to cook up those yummy meals for you and your family! We wanted it to be open and right near the bathroom for convenience! Don’t worry the countertop is spacious as well! We also provide all of the basic essentials and utensils that you may need!brbrThe living room area has a comfy queen sofa sleeper, a mounted flat screen tv and a rocking chair right near the window! Picture yourself having your morning cup of coffee while enjoying the sun rays beaming on you!brbrOur cottage can sleep up to five people comfortably with a little extra space to squeeze in a few more people if needed! We have a queen size bed in the bedroom, a single bed in the living room and also the pull-out sofa sleeper in the living room as well. All beds have fresh linen too!brbrThe bathroom is a tub/shower combination! We also provide two rolls of toilet paper, two rolls of paper towels and a basket of fresh wash cloths! brCheck in at 4 pm please. A keyless entry code will be given to you the morning of your check in (text or call). Check out 10 am please. To help us transition to the next guest, please strip sheets off the beds, place towels in a pile on the bathroom floor, wash dirty dishes, empty out the fridge and freezer, dump coffee grounds out of the coffee maker, and clean up trash outside your cottage. No Smoking inside.

Cottage

Winter Nights Cottages: Cottage 5 Winter, Wisconsin vacation rental.

Winter, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(15)

$289.07

Welcome to The Birchwood @ Moxi Lodge and Lounge... the perfect place to lay your head or enjoy a few craft cocktails or specialty taps in our lakefront lounge!brbrThe lodge is located just a short walk from our private shoreline on Connors Lake. This three-bedroom lower-level unit is the perfect place to unwind and relax after a long day of outdoor fun. We are centrally located in the heart of the Flambeau River State Forest. The forest boasts an astonishing 91,000 acres of public land ready for all of your outdoor recreational activities. Whether you are looking to bag a trophy buck or bass, or love miles of snowmobile/atv and skiing trails... this area has you covered!brbrAll of our units include fully furnished full size kitchens, bed linens, and bath towels/accessories.brbrNot feeling like cooking after an exhausting day outdoors Don't worry, we are just a couple minute drive from two of the Northwoods of Wisconsin's most iconic bar/restaurants!brbrPlease note:br-July/August Rentals: 5 night minimumbr-We have a zero-tolerance guest pet policy. Guests who bring pets on to the property (in the building or otherwise) will be asked to find suitable accommodations for the pet elsewhere or terminate the reservation without refund.

Hotel Resort

The Birchwood @ Moxi Lodge and Lounge

Winter, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(8)

$377.01

Welcome to Three Little Birds Cabin—a cozy, modern-rustic retreat on the serene Chippewa River. This spacious 3-bedroom, 3-bathroom cabin comfortably sleeps up to 8 guests, offering a perfect blend of comfort and nature.brbrProperty Highlights:br-Great for utv enthusiast's br-Directly on snowmobile trails leading to the Chippewa Flowagebr-Level Frontagebr-Modern CabinbrbrThe open-concept living area features a fully equipped kitchen, dining space, and a cozy lounge with a fireplace and river views. Each bedroom is thoughtfully furnished, with plush beds and plenty of storage. Two bedrooms have en-suite bathrooms for added privacy and convenience.brbrStep outside to enjoy a deck overlooking the water, a fire pit for stargazing nights, and direct access to the river for kayaking, fishing, or simply unwinding by the shore. Whether you're planning a family getaway, a couples' retreat, or a group adventure, Three Little Birds Cabin is your peaceful home base in the Northwoods.brbrThree Little Birds Cabin is a haven for snowmobiling and utv riding with the tuscobia state trail only 6 miles away. brbrWinter Activities include ice fishing, snowmobiling, sledding, cross country skiing and much more. brbrLocal attractions include:br-The Wannigan bar 1 mile awaybr-Downtown Winter 6 miles awaybr-Local farmers market's (In-Season)br-Downtown Hayward 32 miles awaybr-Chippewa Flowage 3 miles awaybr-Winter Greenhouse 4 miles awaybr-Fishing Hall of Fame 32 miles awaybr- Tuscobia State Trail 6 miles awaybrbrPlease put all trash in dumpster at the top of the hill.brbrInsects: During the summer there will be plenty of mosquitos so be sure to pack bug spray. We suggest a themacell for sitting around the fire and please keep doors and windows shut to help keep them out.

Private Vacation Home

Spacious Cabin on the Chippewa River

Winter, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(1)

$833.36

*Remaining available stays (flexible three night minimum) for Summer 2026: June 13-20 and August 29 - September 5* brbrEscape to Haven Island, Your Private Northwoods ParadisebrbrAn exclusive retreat in the heart of Wisconsin’s breathtaking Northwoods! This private island offers the ultimate getaway for families, friends, or groups seeking adventure and relaxation. Perfectly accommodating up to 14 guests, this child-friendly and dog-welcoming chalet is your home away from home. Your stay includes a 21’ pontoon boat, kayaks, and a canoe for exploring the sparkling waters.brbrEnjoy the private, lakefront chalet surrounded by scenic wooded trails, multiple docks, and peaceful spots perfect for relaxing or exploring. Soak up the sun and spend time on the water with included kayaks, a canoe, paddle boat, and pontoon! Take a short ride to the lakefront bar and grill, or have ATVs and jet skis delivered right to the property for even more adventure.brbrStep outside and take in the beauty from the wrap-around deck that spans three sides of the home. Spend your days under the outdoor pavilion, ideal for grilling, card games, and lounging. The yard offers plenty of fun with yard games, swimming areas, fishing poles, a shoreline swing, and a flat grill for outdoor cooking.brbrInside the Chalet:brMain Floor includes - brFully equipped kitchenbrSpacious living room with floor-to-ceiling windows and panoramic lake viewsbr3 cozy bedrooms (2 queen beds, 1 full bed)brFull bathroom with walk-in showerbrDining area & electric fireplacebrLaundry roombr3-season room with a queen futon for additional sleeping spacebrAccess to the wrap-around deck with seating for wildlife watching and relaxationbrbrUpper Loft features-brLarge master suite with king log bedbrExecutive bathroom with shower and double vanitybrAdditional small bedroom with bunk bedbrSofa sleeper and space for air mattress or pack-and-playbrbrSleeps 12+ comfortably – Great for families, groups, or couples’ getaways.brbrEase of Access: brConvenient access from the parking area to the boat, with the option to take steps or a step-free path to the chalet. Only four steps to enter the home, and a walk-in shower is available on the main floor. Great accessibility — ideal for guests seeking comfort and ease!brbrAround the Island: brYour private island getaway includes a 2023 21` Sylvan Mirage 8520 Party Fish Pontoon, 2 kayaks, a canoe, a paddle boat, and assortment of water rafts. Kids will love the private swimming areas and they’ll cherish memorable adventures exploring the island. Fish for Musky, Northern, Walleye, and pan fish or enjoy some quiet time. brbrAttractions and Activities: brThis unique island retreat is located along the Tuscobia State Trail, a scenic 74-mile trail great for hiking, biking, ATV & UTV riding, horseback riding, snowmobiling, and bird watching - right through the Northwoods forest.brbrJust 25 miles southeast of Hayward, WI and 1 hour west of Minocqua, you’re a short drive from even more fun!brbrIn Hayward, you’ll find:brMini golf, go-kart racing, and rock climbingbrBatting cages and escape roomsbrGolf courses and nature parksbrGift shops and a zoo/wilderness walkbrbrWhether you’re looking for fishing, boating, swimming, hiking, or just a peaceful place to relax by the lake, this cabin has it all.brbrRoom for six vehicles to park at private easement near dock. Take the included pontoon over to your private island! If you need additional parking space, please contact us.brbrHost will be available via call/text/messaging throughout your stay.brbrBooking Details: brContact us at Jaclyn@locallodging.com before booking if you would prefer to put half down at booking and pay the rest before check in. At booking, a rental and boat agreement will be sent to your email for signature. A $500 boat deposit preauthorization will be placed on the payment method 3 days prior to check out and released at check out unless the boat has been damaged.brYou`ll be staying in someone`s home, so please treat it with care and respect.brbrNo fireworks

Private Island on Lake Winter

Winter, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(8)

$180

This year-round 2 bedroom, 1 bath cabin is the perfect getaway for a family vacation, a couple's long weekend or a friends fishing/ATV/snowmobiling trip!brbrThis 1000 sqft cabin sits on a private 1.5+ acre lot surrounded in towering pines, which provides plenty of shade over the property. Enjoy 200 feet of lake frontage with private dock and plenty of water toys including: fishing poles, 2 kayaks, Aqua Lily Pad, paddle boat, 2 stand-up paddle board with life jackets and beach towels.brbrWinter Lake is 733 acres, 22 ft deep and features Musky, Panfish, Largemouth Bass, Smallmouth Bass and Walleye per the WDNR. There are 2 public boat landings. brbrYou'll enjoy easy access to the snowmobile and ATV/UTV trail systems offering literally hundreds of miles of groomed trails throughout northern Wisconsin.brbrMaximize your time and money with early check-in (2:00pm) and late checkout (1:00 pm). brbrOther amenities include gas and charcoal grill, fire pit including wood, wood-burning fireplace, board games and puzzles. Two separate desk areas include monitors, keyboard and mouse—just bring your laptop and docking station! brbrA variety of bar & grill and supper clubs are scattered throughout the area and along the 30 mile drive to Hayward. The small town of Winter has everything you need: gas station, food co-op, hardware store, bars, cafe, and a library. brbrThere is a $75 pet fee per animal.br

Private, Pet Friendly Lakefront Cabin

Winter, Wisconsin, United States

Bed

Bath

Sleeps

Exceptional(2)

$133.99

Welcome to our cozy one-bedroom humble abode! This cottage is nestled away in the quiet town of WInter, WI. During your stay you will have direct access to the Tuscobia trail system for UTV and Snowmobiling. Winter is surrounded by lakes that are great for fishing or recreational uses. If you are into hiking and skiing there are multiple trail systems to enjoy such as the Tuscobia Trails, Flambeau Forest State Forest, Oxbo Pines State Natural Area and the American Birkebeiner Trail. These cottages are great for family trips, a romantic getaway and more! Our cottages sleep anywhere from 1 up to seven people comfortably.brbrThe kitchen is fully stocked with all of the basic essentials that you may need to cook up those delicious meals, such as a fridge, utensils, coffee maker, stove top, and microwave. We’ve got you covered!brbrEach bed has fresh linens and multiple pillows to make you feel right at home.brbrThe bathroom area has towels ready to use for showers and is already stocked with two full rolls of toilet paper and two rolls of paper towels. Check in at 4 pm please. A keyless entry code will be given to you the morning of your check in (text or call). Check out 10 am please. To help us transition to the next guest, please strip sheets off the beds, place towels in a pile on the bathroom floor, wash dirty dishes, empty out the fridge and freezer, dump coffee grounds out of the coffee maker, and clean up trash outside your cottage. No Smoking inside.

Cottage

Winter Nights Cottages: Cottage 1 Winter, Wisconsin vacation rental.

Winter, Wisconsin, United States

Bed

Bath

Sleeps

$326.52

Welcome to our cozy 3 bedroom, 1 bathroom cabin(newly constructed), the perfect place for year-round fun! Nestled just 0.25 miles away from the trail system, our cabin offers the ultimate convenience for outdoor enthusiasts.brbrOur cabin features an open concept design, with tons of windows and natural light flooding the space. Whether you're snuggled up on the couch or cooking in the kitchen, you'll feel right at home. Step outside onto the deck to enjoy the fresh air and stunning views.brbrThe basement has a game room, complete with an air hockey table, foosball table, a dart board, and plenty of space to hang out with friends and family. After a long day of hiking, biking, or hanging out on the water unwind on the deck or catch your favorite movie on the flat-screen TV.brbrWhether you're looking for a quiet weekend getaway or an action-packed adventure, our cabin is the perfect destination. Book your stay today and experience all the fun our beautiful lake has to offer!

Welcome to The Hideaway on Highland.

Winter, Wisconsin, United States

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Sleeps

Most popular vacation rentals in Winter

$1899.00

Lodge

Historic prohibition Lodge next to golf course with private beach

Winter, Wisconsin, United States

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Bath

Sleeps

$168.80

Right on the Tuscobia Trail Cozy 2-bedroom cabin in Winter with WiFi, AC

Winter, Wisconsin, United States

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Bath

Sleeps

$168.80

Classic Rustic Lakeside Cabin Retreat. Sleeps 6. Pets allowed.

Winter, Wisconsin, United States

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Bath

Sleeps

$183.57

Cozy cabin on Island Lake

Winter, Wisconsin, United States

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Bath

Sleeps

$191.66

Cabin in the Woods Near Big Chip and Hayward

Winter, Wisconsin, United States

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Bath

Sleeps

$200.62

Pets & kid Friendly ,direct access to ATV& snow trails, private dock

Winter, Wisconsin, United States

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Bath

Sleeps

$211.00

Bobbers Cabin on Perch Lake

Winter, Wisconsin, United States

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Sleeps

$262.70

Hotel resort

\"The Loft\" @ Moxi Lodge and Lounge

Winter, Wisconsin, United States

Bed

Bath

Sleeps

$303.81

Pfaff Winter Retreat on Lake Winter. Minutes from Tuscobia trail.

Winter, Wisconsin, United States

Bed

Bath

Sleeps

$833.36