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Holiday Rentals in Winchester

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    All 30 Rentals in Winchester
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    Winchester
    6 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
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    Winchester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Winchester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    The following rentals are within 15 kilometres of Winchester.
    Manitowish Waters
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Washer
    • DVD Player
    • Grill
    • Waterfront
    • Patio
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My parents built their dream lake house about 15 years ago for vacations (family gatherings) and built it large to accommodate 12 plus guests. High vaulted ceilings, stone fireplace, unique furnishings and two stories of windows give a exceptional view of Big Lake and all it's beauty. The...
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    Manitowish Waters, Wisconsin 54545
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Manitowish Waters
    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Washer
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grand Getaway Begin your lakefront vacation in style at this luxurious, newly constructed, family-friendly home on 100 feet of ripple-sand frontage on Rest Lake, part of the sought-after Manitowish Waters Chain of 10 Lakes in Northern Wisconsin. Wake up early for coffee on the spacious deck, and...
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    Manitowish Waters, Wisconsin 54545
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
    Manitowish Waters
    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • DVD Player
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Spider Lake Shores Relax in style at Spider Lake Shores! This gorgeous, luxury, family-friendly home is amassed with style, comfort, and plenty of space for everyone in your group. Enjoy time around the outdoor firepit or relax in the three season, screened-in porch! This rental also boasts...
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    Manitowish Waters, Wisconsin 54545
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 15
    Presque Isle
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    White House The White House, a restored country home, sits on a remarkable 160 acres of private land in the Northwoods of Presque Isle. The updated vintage interior blends old-fashioned charm with plenty of modern conveniences, and the view of the neighboring pond will make your morning coffee...
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    Presque Isle, Wisconsin 54557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Presque Isle
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Last Wilderness Comfortable and inviting home in sought-after Presque Isle Lake, part of a tranquil three lake chain! Relax on the spacious deck as you watch for bald eagles, listen to the loons, or catch a glimpse of the many wood ducks and great blue herons. Venture down to your private pier...
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    Presque Isle, Wisconsin 54557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Presque Isle
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Balcony
    • Wi-Fi
    • Waterfront
    • Terrace
    • Cable/satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lynx Lakeside Relax in the Northwoods in this cozy home on the northern shores of Lynx Lake. Situated perfectly to experience both a quiet sunrise and gorgeous sunset, this home has endless sunshine all day long. There's even a firepit provided to make your Northwoods evenings complete. Gather next...
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    Presque Isle, Wisconsin 54557
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Presque Isle
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Waterfront
    • Washer
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    • Patio
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There and Back Again Recently updated with new furnishings, this beautiful, dog-friendly, chalet-style home sits on the sunny eastern shores of Presque Isle Lake, the premier recreational and trophy fishing lake of the Northwoods. Enjoy stunning water views through the large windows inside as well...
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    Presque Isle, Wisconsin 54557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Manitowish Waters
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bay Hideaway Bay Hideaway is the perfect vacation rental for a large group to stay and play in Manitowish Waters. This modern-rustic cabin is conveniently located with access to the Manitowish Chain of 10 Lakes as well as the area’s endless trails for any passion - mountain biking, road biking,...
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    Manitowish Waters, Wisconsin 54545
    Cabin Holiday Rental - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Manitowish Waters
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lake Junction This lakeside retreat in Manitowish Waters is the perfect lodging for your next getaway to the Northwoods of Wisconsin. Featuring a private front porch, access to a shared patio and fire pit area, as well as free WiFi, this unit is perfect for family or group adventures. While there...
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    Manitowish Waters, Wisconsin 54545
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Presque Isle
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
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    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Green Haven Fill your senses with the fresh northern air in Presque Isle at this comfortable and spacious lakefront home on Lynx Lake. Gorgeous lake views and all-day sunshine make this home the hidden gem you've been searching for. Enjoy time on the expansive deck with spectacular views of Twin...
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    Presque Isle, Wisconsin 54557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Manitowish Waters
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
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    • Central Heating
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Artist's Cove From fun in the sun to cozy nights by the fire, Destination Cove is the perfect retreat for whatever your heart desires. With a waterfront location on the shores of Wild Rice Lake (as well as a dock, two kayaks, and a rowboat to help you explore), Destination Cove offers the...
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    Manitowish Waters, Wisconsin 54545
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Manitowish Waters
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Director's House Scenically situated on the grounds of the Discovery Center in a stand of pines overlooking Statehouse Lake, this beautiful, lakefront home is the perfect Northwoods getaway! Come escape into lovely Manitowish Waters and be sure to bring your dog along for the wonderful holiday....
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    Manitowish Waters, Wisconsin 54545
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Manitowish Waters
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cast Away Located on the Manitowish River, just around the bend from Stone Lake, Cast Away is the ideal landing spot for Northwoods lake lovers who want to explore the Manitowish Chain of 10 Lakes by water. Hop in your rowboat from the private pier and head down the river, or put in your fishing...
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    Manitowish Waters, Wisconsin 54545
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Lakefront Mercer Cabin w/2 Lofts, Fire Pit & Porch1 / 24
    (1)Excellent
    Mercer
    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2018
    God’s country! The views were spectacular! Lounged on the front porch while enjoying our morning coffee. The rustic cabin has modern comforts, but kept its beautiful, original...
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    Escape the stresses of everyday life during your stay at this historic vacation rental cabin in Mercer, located on Lake of the Falls! The 1-bedroom, 1-bathroom rustic log cabin features 2 spacious lofts and can accommodate 8 guests on a once-in-a-lifetime trip to the Northwoods. Originally built in...
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    Mercer, Wisconsin 54547
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 8
    New Family Friendly Vacation Home On Presque Isle Chain-Of-Lakes In Northern WI1 / 25
    (3)Excellent
    Presque Isle
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Wi-Fi
    • Parking
    • Balcony
    • Patio
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    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2018
    Alpine Resort is the place my family and I look forward to going to every year! It is a gem tucked away in the northwood of Wisconsin that allows you and your family to sit...
    Reviewed 9 August 2018
    It was a great get away. Close enough that I could drive from Chicago area with my kids. So much for the kids to do. Fishing, paddle board, kayaking, boats, etc. couldn't have...
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    About this property
    Aspens is a four bedroom/two bath home/cabin with a spacious open concept living room/dining room, large outside deck and central air conditioning. The cabin has western exposure on Van Vliet Lake, part of the Presque Isle chain of lakes, from the kitchen and deck, and northern exposure of the lake...
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    Presque Isle, Wisconsin 54557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Presque Isle
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Housekeeping Included
    • Balcony
    • Grill
    • Patio
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    • Washer
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on a hillside of Presque Isle Lake's east shore, this custom, open concept home has just what you need to enjoy all four seasons. This home was previously listed on Northwoods Home Rentals. Oversized bedrooms and multiple living areas allow for plenty of room to relax. The home has a...
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    Presque Isle, Wisconsin 54557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Manitowish Waters
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Terrace
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It's 8 O'clock Somewhere There is nothing left to be desired when staying at this beautiful lakefront property in Manitowish Waters! Recently updated with all the luxurious comforts of home, inside you'll find open concept living and dining space next to a fully-equipped kitchen that will channel...
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    Manitowish Waters, Wisconsin 54545
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Presque Isle
    3 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vanvilet Lakehouse The beauty of Northern Wisconsin awaits at this lovely, lakefront cabin. Featuring three levels, a large yard, and multiple living areas, there is plenty of room here for the whole family. With a private dock, you'll spend many a sunny day swimming in the waters of Van Vliet...
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    Presque Isle, Wisconsin 54557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 14
    Mercer
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Hemlocks Retreat - Lakewood Upper www.thehemlocksretreat com Unwind and enjoy the wonderful lake views from our fully restored and thoughtfully updated lakefront cabin. Towering hemlocks, soaring eagles, wonderful sound of loons. Mercer, WI is the loon capital of the world. Flat screen TV in...
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    Mercer, Wisconsin 54547
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Manitowish Waters
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Central Heating
    • Terrace
    • Skiing: Property Is In A Ski Resort
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **Please note that there is another vacation rental unit on the premises, and there may be other travelers present during your stay** Retreat to the serene Wisconsin lakes by booking this 1-bedroom, 1-bath vacation rental cabin in Winchester, located on South Turtle Lake amidst a forested...
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    Manitowish Waters, Wisconsin 54545
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Mercer
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Patio
    • Waterfront
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Hemlocks Retreat - Lakewood Lower www thehemlocksretreat com Peaceful Privacy Lakeside, w/Dock, Great Sunsets, Free Wi-Fi & Cable Mercer, WI Unwind and enjoy the wonderful lake views from our fully restored and thoughtfully updated lakefront cabin. Towering hemlocks, soaring eagles,...
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    Mercer, Wisconsin 54547
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Manitowish Waters
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
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    Experience the feeling of a traditional Northwoods Resort at Cast Away cabin in Manitowish Waters. Part of the historic Hillcrest Resort, this quaint vacation rental will transport you to another era when fishing and family vacations were a staple of an Up North summer. Located on the Manitowish...
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    Manitowish Waters, Wisconsin 54545
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Mercer
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We acquired a few rustic cabins in the old Evergreen Resort and Lake Tahoe Lodge on Twin Tahoe Lakes on Lake Tahoe in Mercer. ​A booming resort nestled on a private lake in the 1930's, this place has seen visitors from the era of gangsters that stayed in the northwoods. ​As we continue to bring...
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    Mercer, Wisconsin 54547
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Mercer
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We acquired a few rustic cabins in the old Evergreen Resort and Lake Tahoe Lodge on Twin Tahoe Lakes on Lake Tahoe in Mercer. A booming resort nestled on a private lake in the 1930's, this place has seen visitors from the era of gangsters that stayed in the northwoods. As we continue to bring...
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    Mercer, Wisconsin 54547
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Manitowish Waters
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Skiing: Property Is In A Ski Resort
    • Grill
    • Wi-Fi
    • Balcony
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that there is another vacation rental unit on the premises, and there may be other travelers present during your stay ** Love life on the lake? Have a passion for fishing? This vacation rental studio, which sleeps 2, is the perfect place to take a break from the norm and enjoy...
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    Manitowish Waters, Wisconsin 54545
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Manitowish Waters
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Wi-Fi
    • Central Heating
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note that there is another vacation rental unit on the premises, and there may be other travelers present during your stay* Forget your cell phone, pack your fishing rod and step into this outdoorsman's paradise. Nestled on the shores of South Turtle Lake in Winchester, this 1-bedroom,...
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    Manitowish Waters, Wisconsin 54545
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 6
    Manitowish Waters
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Central Heating
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note that there is another vacation rental unit on the premises, and there may be other travelers present during your stay* Grab a friend and enjoy some rest and relaxation at this 1-bathroom vacation rental studio which sleeps 2, perfect for any outdoor adventurer. Whether you're a...
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    Manitowish Waters, Wisconsin 54545
    Condo/Apartment - 1 Bathroom, Sleeps 2
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