Holiday rentals in Sinissippi Lake

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Top-rated holiday rentals in Sinissippi Lake

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Top guest favourite
Home in Wales
4.94 out of 5 average rating, 195 reviews

Beautifully Restored Historic Victorian

Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

Top guest favourite
A red door with a decorative wreath opens to a outdoor patio area, featuring a comfortable seating arrangement and potted flowers. Lush greenery surrounds the space, enhancing the connection to nature, with a glimpse of the lake in the background.
Cabin in Fox Lake
4.96 out of 5 average rating, 225 reviews

Cabin on the Trail

Kick back and relax in this cozy space with up north, cabin vibes. In the summer months enjoy the excellent fishing and boating and in the winter have fun ice fishing on beautiful Fox Lake! *Please read the full description and look at all of the pictures of the property *Not suitable for parties or loud gatherings. Please note, there is a 4 person maximum *All dogs/pets must be pre-approved by the host. There is a $50 pet fee/stay. *Check out our “cottage on the trail”, closer to the lake.

Superhost
A two-story house features a blue exterior with large windows illuminated by natural light. Lush green shrubs flank the entrance, while a small seating area consisting of metal chairs is set on a well-maintained lawn. A concrete path leads to the front door.
Home in Oconomowoc
4.85 out of 5 average rating, 105 reviews

Oconomowoc Downtown River View

Stunning view of the Oconomowoc river, locate in the heart of downtown Oconomowoc. Whether you are traveling for fun or work there is something for everyone. Walk to sandy beaches, six nearby parks, tennis court, or just walk around beautiful Lac La Belle Lake and Fowler Lake. Bring your kayaks or boat. Local boat rentals are available in town. Enjoy live bands and events at restaurants and bars or have a peaceful dinner at one of many fine dining restaurants also in walking distance.

Top guest favourite
A welcoming front porch is framed by lush gardens and colorful flower beds. A pathway of natural stones leads to a wooden door, while wicker chairs and loveseats are arranged under the porch beams. Hanging plants add a touch of greenery to the inviting entrance.
Guest suite in Sussex
4.96 out of 5 average rating, 324 reviews

The Loft @ The Butler Place. 1846 homestead.

The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.

Superhost
A red kayak rests on the green lawn, positioned near the lakefront rental home. The home features a spacious outdoor patio with seating, framed by trees, and offers a relaxed setting for enjoying the natural surroundings.
Home in Juneau
4.85 out of 5 average rating, 151 reviews

Take a Break at Lakeside Acres

Lakeside Acres; a 2-bedroom, 1 bath vacation rental home located on beautiful Lake Sinissippi. Open concept living area with furnished patio and private dock. This home provides the perfect summer getaway or winter retreat for family and friends. Whether you spend your days kayaking with the complimentary kayaks, exploring Horicon Marsh, or soaking up the sun on the dock, you're sure to have an unforgettable stay in this lakefront hideaway. Note: Docks are not in the lake Nov-Apr.

Top guest favourite
Cabin in Cascade
5 out of 5 average rating, 226 reviews

hot tub and sauna on 5 private acres

Looking for a cozy winter retreat? Experience the Bird House, a tranquil Scandinavian-inspired private woodland paradise. Melt away stress in the hot tub and infrared sauna as you take in peaceful views of the meadow. Explore snowshoe and cross-country ski trails nearby in the scenic Kettle Moraine. Stream your favorite movie on the projector near the fireplace or unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee.

Guest favourite
A brightly colored living area features an orange couch with patterned cushions, complemented by a unique coffee table. A round ottoman sits nearby, while large windows allow ample natural light. Open shelving holds decorative items, enhancing the vibrant atmosphere of the open-concept space.
Home in Milwaukee
4.94 out of 5 average rating, 133 reviews

Bright 1.5BR in the Heart of Bay View - w/ Parking

Perfectly located in Milwaukee’s eclectic Bay View 4 blocks from the lake. Minutes from downtown, Summerfest, art museum, etc. You’ll have the entire second floor of this sunny duplex. The space is open concept - 1 bed with a King Casper mattresses, a bright kitchen with tons of space, a stylish living room with art throughout, and an office (with an air mattress). Fenced-in back yard that's great for pets and chill around the outdoor table for optimal hangs and BBQs.

Top guest favourite
The image depicts a charming three-building arrangement situated on a cul-de-sac. The structures feature varying architectural styles with a mix of siding colors. Lush greenery is visible in the surrounding landscape, and an American flag is displayed on one of the buildings under a blue sky with scattered clouds.
Guest suite in Deerfield
4.96 out of 5 average rating, 162 reviews

Studio on the Prairie Fen

Kick back and relax at the Studio! The Studio is a 400 sq ft unique suite in the lower level of our home. A private locked entrance opens up to a sunny space with great views of a wetland beyond the backyard. Private patio to enjoy morning coffee and the sunrise. A great place to unwind and enjoy nature's beauty! We have binoculars if you love bird watching, and bikes to ride or hike the Glacial Drumlin Trail just 0.1 mile from the front door. Lic LICHMD-2021-00621.

Guest favourite
A serene lake scene is captured at sunset, reflecting warm hues of orange and yellow across the water's surface. Gentle ripples create an intricate pattern, while trees line the shoreline, adding to the tranquil atmosphere.
Cabin in Hustisford
4.87 out of 5 average rating, 39 reviews

Firefly Cabin, a Unique Tranquil Space

Get ready for a relaxing getaway with your friends and family. Firefly Cabin has a lakehouse feel with all the comforts of home. This charming Cabin is only an hour drive from Milwaukee or Madison. It is the sister Cabin to Serenity Cottage, rent one or both! Please note Firefly Cabin does have stairs to main living area and areas of lower ceilings. This relaxing retreat won't disappoint and is a great option for a remote workers or a quick getaway from the city.

Top guest favourite
The exterior of a two-story blue lakeside home is displayed, featuring large windows that allow for ample natural light. Adjoining the home, a well-maintained lawn is complemented by a fire pit area with light green Adirondack chairs, creating an inviting outdoor space.
Home in Beaver Dam
4.92 out of 5 average rating, 147 reviews

LakeLife is Dam Good! 4 Bedroom Waterfront Home

Fun for the whole family at this stylish lakeside home in the heart of Beaver Dam. The house as everything a group needs and wants for the perfect weekend, week, or overnight adventure. From the open floor plan living room to the exposed game room basement that leads right out to the lakeside yard. We've filled this home with all the touches needed to guarantee lake life living. The backyard overlooks thousands of acres of lake with endless lake views.

Top guest favourite
A charming cottage is located near the water's edge, framed by lush green grass and a few trees. Outdoor equipment, including kayaks and a table setup for dining, adds convenience for guests. The exterior is painted in a soft blue, enhancing its inviting appearance.
Cottage in Hustisford
4.96 out of 5 average rating, 130 reviews

Charming and Cozy Cottage on Lake Sinissippi!

Pine Shore Retreat is a charming cottage so close to the lake that you feel like you are in a houseboat! The east side location means you have fabulous sunset views, as well as swimmable, hard bottom frontage off the platform pier. It is a small space, just one bedroom, but very cozy. Comfort is the focus, with new, high-end furnishings. The stainless steel refrigerator, granite countertops and a gas range in the kitchen offer a higher end experience.

Top guest favourite
A charming bungalow is positioned near the edge of the Rock River. A well-maintained pathway leads up to the entrance, with vibrant greenery surrounding the area. The tranquil water reflects soft light, enhancing the serene setting.
Guest house in Horicon
5 out of 5 average rating, 26 reviews

Boathouse Bungalow

The Rock River Retreat Boathouse Bungalow is adjacent to the Rock River in the rural countryside of Dodge County, home of the treasured Horicon Marsh. Relax, refresh, and enjoy this magical place and the natural beauty that surrounds it. Discover and explore our undisturbed marshland by kayak, boat, or canoe. Spend time birding, biking, or hiking through this unique environment. Please join us for your time of connecting, discovery, and surprise.

Popular amenities for Sinissippi Lake holiday rentals