Holiday rentals in Chain O' Lakes

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Top-rated holiday rentals in Chain O' Lakes

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A charming cabin is nestled by the water, featuring a covered porch with seating and a simple wood structure. Lush greenery surrounds the area, while a wooden dock extends into the lake. Kayaks and paddleboards are positioned nearby, emphasizing the waterfront access.
Cottage in Waupaca
4.77 out of 5 average rating, 13 reviews

Cheerful waterfront cottage right on Taylor Lake

A delightful waterfront property perfect for all of your family and friends! Directly on Taylor Lake, we are close to all the activities that the chain is famous for. Plenty of indoor and out door living areas with kayaks and paddle boards, a pier to moor your boat along with all the other amenities to make your stay enjoyable, we have it all! During the winter months, curl up next to the wood burning fireplace and relax while taking in the views, after a successful day hunting or snowmobiling

Guest favourite
A tranquil lakefront view displays a spacious home set amidst vibrant trees. The property includes a large grassy area, with a blue dock and several seating options, creating a welcoming space for relaxation. The scene reflects the beauty of nature and peaceful surroundings.
Home in Waupaca
4.85 out of 5 average rating, 166 reviews

Private Tranquil Escape on Miner. Chain O’Lakes

PRIVATE Yr Rd lake home on Miner Lake, perfect for family gatherings. Sleeps 10-12, fully equipped kitchen, dock and 100' recreation frontage on the beautiful Chain O' Lakes. Woods and huge yards surround all sides of this gem. ***PEAK ANNUAL SUMMER SEASONS-June through August : 7-nt min. Must be a Sat.- to Saturday check-in. Pontoon avail for additional fee. $699tx Fall, winter & spring are also great to visit the area for hunting, (ice) fishing trips, skiing, snowmobile. 2-night off-ssn min.

Guest favourite
A spacious outdoor deck features comfortable lounge seating and a dining area. The modern design is complemented by natural wood accents. Surrounding trees display autumn foliage, creating a tranquil setting. Sunlight gently illuminates the area, enhancing the inviting atmosphere.
Cabin in Waupaca
4.9 out of 5 average rating, 63 reviews

Otter Lodge on the Chain o’ Lakes

Perfect year round home on Waupaca's Chain o' Lakes. Private 4bed/2bath sits on 1.75 acres with over 100ft of lake frontage. Located on Otter Lake, enjoy the quiet of a no-wake lake with easy access to the adjacent fast lakes. Kayaks, paddle boards, Maui Mat, fishing poles and floats included for use. Dock access for boat on property and one street from public boat launch. Summer: June 4 night min, July/Aug 5 night min* Overflow or lower price - see "Whispering Pines" on Ottman Lake *exceptions

Top guest favourite
The exterior of the home showcases a single-story structure with a stone facade and a welcoming front door. A well-maintained lawn is bordered by a concrete walkway, with mature trees adding greenery to the setting. A chimney is visible on the roof.
Home in Waupaca
4.95 out of 5 average rating, 215 reviews

Entire House, hot tub, dogs, way cool bathrooms.

Wonderful open concept living featuring eat in kitchen/dining area, living space with a beautiful gas fireplace, fenced in yard, clamshell & sunken tub showers, and tasteful décor, relaxing. Waupaca is centrally located to many places you may wish to go. We have a beautiful park system, 22 connected lakes, wonderful culture, arts, library, main street, and best of all friendly people. Outdoors is fishing, silent sports, kayaking, tubing, hiking trails, and so much more. ATV/UTV friendly.

Top guest favourite
Cabin in Wild Rose
4.98 out of 5 average rating, 92 reviews

Cozy Cabin on a Lake

Come enjoy our cozy cabin nestled in the pines with frontage on a quiet lake. An all-season retreat: Kayak, fish, and swim from the dock during late spring, summer, and early fall. Boat and waterski during summer -it's a full recreational lake. Drive five minutes to Nordic Mountain - perfect for late spring, summer, and fall mountain biking or winter and early spring skiing and tubing. Enjoy the beautiful nature and lake views from inside the charmingly decorated home any time of year!

Top guest favourite
A spacious studio apartment is highlighted by a large, unique chandelier above the bed. Natural light floods the area through multiple windows, illuminating the polished wooden floors and cozy seating arrangement. The open layout includes a kitchenette visible in the background, enhancing the inviting atmosphere.
Loft in Amherst
4.96 out of 5 average rating, 199 reviews

Tiny Town Bakery Flatlet

Ever wanted to see what goes on in a commercial bakery? Imagine waking to the aroma of baking bread and cinnamon rolls? Get a bird's eye view into the kitchen of the Village Hive Bakery Kitchen while staying in the newly renovated "flatlet". Salvaged & repurposed building supplies used to create a unique studio apartment above the bakery retail. Guests can enjoy the retail farmhouse table and comfortable seating space by the Main Street picture window. Cooking/baking classes available.

Top guest favourite
The view showcases a tranquil lake surrounded by trees, with the clear blue water reflecting sunlight. A wooden dock extends into the lake, alongside a grassy area featuring a seating arrangement of white chairs and a fire pit, providing a peaceful outdoor setting.
Cottage in Waupaca
5 out of 5 average rating, 14 reviews

Lakefront Cottage with Sandy Shore & Sunset Views

Steps from the sandy shore-line, spring fed crystal clear water, on Stratton Lake. Enjoy fishing, swimming, and boating during the day with sunset views and campfires at night. Kayaks, paddleboards, paddle boat, and swim raft are available for use or bring your own boat and tie off on the dock. Minutes from shops, entertainment, attractions, restaurants and the Chain O' Lakes. The perfect location for your lakeside get-away! Note: Host may ask for ID verification related to compliance.

Top guest favourite
A private fishing dock extends into the calm water, framed by tall trees and vibrant flower arrangements. Sunlight filters through the leaves, casting gentle shadows on the grassy shoreline adjacent to the lake.
Flat in Waupaca
4.98 out of 5 average rating, 194 reviews

Columbia Lake Sunset View

Beautiful apartment on Columbia Lake on the Chain 'O Lakes. Private deck and fishing dock. Perfect location for kayaking, fishing, or any other water recreational activity. Walking distance to two restaurants, two marinas and ice cream shop. Close to Hartman Creek State Park to access trails. Please be aware that a close venue has bands/music that can easily be heard when outside and the music may be heard when indoors. Three night minimum Memorial Day weekend - Labor Day weekend.

Top guest favourite
The exterior of a cabin is depicted, featuring large windows framed by wood. Warm light emanates from within, revealing a cozy interior with a lamp and seating. Snow covers the ground, and icicles hang from the roof, creating a serene winter scene.
Cabin in New London
4.99 out of 5 average rating, 122 reviews

Secluded Cabin with Sauna - Discounted till 6/1

Place yourself in nature. Put down your phone and pick up a book. Clear your mind, focus on your breath, connect with your inner self. Sleep like you’ve never slept before accompanied only by the sound of owls and wind in the pines. The Belden Farm offers land that is a true retreat. Enjoy the privacy and quiet of our cabin in the woods. Extensive, well-maintained trails for hiking, skiing or Fattire biking lead you through towering hardwoods, cathedral white pines, and golden meadows.

Top guest favourite
A long, private pier extends over calm waters, with a small boat docked nearby. Two children are joyfully leaping from the edge of the pier. A foam swimming raft is visible on the water, surrounded by lush greenery lining the lakeshore.
Cabin in Wautoma
4.98 out of 5 average rating, 103 reviews

Cozy A-Frame w/a View: Fishing, Boating, Hot Tub!

Relax in peace and experience “Up North” vibes without the long drive. Perfect for families, a girls’ getaway, or a romantic retreat. 🌊 Panoramic views of Little Hills Lake 🛁 Hot tub 🐾 Pet-friendly 🛶 Private dock and raft on crystal clear lake 🚤 Motorboat rentals available (with dropoff) 🍽️ Great dining and shopping minutes away in Wautoma ⛷️ 15 minutes to skiing & tubing at Nordic Mountain 🚗 1.5 hrs from Madison | 2 hrs from Milwaukee | 3.5 hrs from Chicago

Top guest favourite
The exterior of a modern home is framed by tall pine trees, dusted with snow. A car is parked under an attached carport on one side, while large windows provide a glimpse into the interior. The sleek design complements the serene wooded environment.
Home in Waupaca
4.99 out of 5 average rating, 148 reviews

The Raven

Nestled in a quiet, wooded neighborhood, The Raven boasts all the comforts and conveniences of home while offering the peace that only comes when you get away from it all. We're just ten minutes from charming restaurants, local shops, the chain of lakes, and only five minutes from Hartman Creek State Park and the Ice Age National Scenic Trail. Whether to relax, to recharge, or to explore, welcome to your modern escape to the woods. Welcome to The Raven.

Top guest favourite
An outdoor seating area is arranged around a fire pit, featuring several chairs in blue and red hues. A well-maintained lawn is flanked by lush greenery, with a welcoming entrance to the house visible in the background. An American flag stands at the side of the path.
Home in Waupaca
5 out of 5 average rating, 34 reviews

Waterfront house on Miner Lake- Waupaca Chain

Relax with family and friends at this peaceful lakefront property on the clear and sandy Miner Lake, located on the majestic Waupaca Chain O' Lakes. Miner is a deep, no wake lake that is great for fishing, swimming, kayaking, or just relaxing. Within walking distance to classic Chain restaurants-Wheelhouse and Indian Crossing Casino. Staying in for the night? Enjoy the gas grill, fire pit, bar area, and TV's.

Popular amenities for Chain O' Lakes holiday rentals