Vacation rentals in Waupun

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Top-rated vacation rentals in Waupun

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

A lakeside view of a vacation rental home is visible, situated on a spacious lawn surrounded by trees. A private dock extends into the calm waters of Lake Sinissippi, reflecting the serene landscape and clear sky.

Home in Juneau

4.85 out of 5 average rating, 133 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 newly updated 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 favorite

Apartment in Cedarburg

4.97 out of 5 average rating, 348 reviews

Cedarburg 2 br Apartment on prime Washington Ave

Prime location in Historic Cedarburg on Washington Ave in the heart of it all in a 2br apartment w/NO CLEANING FEE(short to do list at checkout).Guests get special attention that they deserve in a stylish calm space, above a 3 car garage accessed by stairs set back off of the street for a quiet timeout. So much to do & see or simply take a walk/picnic in the park. Just steps to shops, restaurants, wineries, & breweries set back off the street. Close to bike/hike trails, golf, museums, parks...

Guest favorite

A shaded outdoor sitting area features comfortable wicker chairs and a glass-top table. The colorful rug adds vibrancy, while views of the lake and greenery are visible in the background. Hanging plants and string lights enhance the inviting outdoor space.

Home in Winneconne

4.92 out of 5 average rating, 48 reviews

Reel in the Fun: @ Lakeside Getaways Lake Poygan

Make some memories at this unique and family-friendly place. This is a great lakeside home close to some of the best fishing spots on the lake. The lake has a sandy bottom where the kids can enjoy swimming or kayaking. Fish off the dock or bring your boat and enjoy the whole lake. It is only a 4 minute drive to the boat landing and bait shop. Launch your boat once and leave it on the boat lift. Boat to many waterfront restaurants or drive to many nearby restaurants and supper clubs.

Guest favorite

Apartment in Port Washington

4.91 out of 5 average rating, 139 reviews

Lighthouse View -a real gem on Sweet Cake Hill

Enjoy the view of the Port Washington Lighthouse, Marina, and Lake Michigan from your private 1 queen bedroom (plus 2 futons in Living room) upper bungalow apartment. Our house was built in 1900 it has older architectural features. Please look at all the pictures. Private entrance, bathroom, and kitchen with range and refrigerator. Living room has plenty of seating and smart TV. Two block walk to the downtown with 17 restaurants and pubs within walking distance. Only 3 blocks to the marina!

Superhost

The cabin's outdoor deck is surrounded by lush greenery and features comfortable hanging chairs and colorful seating. Warm string lights illuminate the space, enhancing the inviting atmosphere. The modern A-frame structure stands amidst the trees, showcasing large windows that offer a glimpse of the interior.

Home in Wautoma

4.9 out of 5 average rating, 105 reviews

Lake Getaway with Escape Room, Speakeasy & Hot Tub

This fully remodeled a-frame style cabin sits in the old forest of Lake Alpine: perfect for a family or couple getaway. Lake Escape has all the things you’d expect from a lake house getaway: lake/beach access, kayaks, canoe, swimming, fishing, hot tub, board games, yard games, dock. But, Lake Escape has so many bonus secrets hidden within! You'll discover a built in escape room, bookshelf doors, tricky puzzles, underground speakeasy, put-put golf, 90s video games, private forest, and more!

Top guest favorite

Home in Oshkosh

5 out of 5 average rating, 36 reviews

WolfDen Getaway - Winnebago Channel

5/5 Rating on another travel site (55 Reviews) - "The Wolf Den is by far the best home our family has rented..." - 6/29/2023 You’re only a 1/4 mile from the boat launch. The channel allows you to dock your boat at the property during your stay. It’s a large home with plenty of space with a newly renovated lower level, including a pool table, ping pong, darts and foosball. Smart TVs in all the right places. 4 bedrooms/3 bathrooms. Plenty of parking. Brand new queen size murphy bed.

Top guest favorite

A covered porch features two lounge chairs and a small table, accompanied by a glass of water and a book. The serene view of the lake is visible through the wooden railing, with green trees surrounding the area.

Cottage in Hancock

4.98 out of 5 average rating, 56 reviews

Stone Have Lake cottage -Stunning views!

We would love to host you at our newly updated, fully furnished cottage on the water! Enjoy lake sunrises right from the porch. This centrally located cottage is perfect if you're looking for that "Up North" feel and wanting to unplug with friends/family. Pine Lake is small & quiet, while still having the benefits of a full rec lake. It also offers some of the best fishing in the area. The lake consists of Musky, Panfish, Largemouth Bass, Smallmouth Bass, Northern Pike, and Walleye!

Guest favorite

A comfortable living area is highlighted by a soft sofa and armchair, accompanied by a stylish coffee table. A wall display features a cityscape artwork, while a lamp provides warm lighting. Natural light enters through large windows, enhancing the welcoming ambiance.

Home in West Allis

4.9 out of 5 average rating, 147 reviews

KING BED/Amazing Location/Free parking/Wi-Fi

Enjoy a fun and relaxing stay with family or friends in this stylish, cozy, and comfortable lower unit, which features: 2 bedrooms (1 king, 1 queen ) 1 bathroom Fully equipped kitchen with dining table and designated coffee bar Living room with a 65” smart TV (Netflix included) Home office space Free parking spot Located just a short drive (4 min) from I94, this home offers easy access to all the city's major attractions * the ideal base for exploring the best of Milwaukee

Top guest favorite

An outdoor seating area features a hanging chair and a cozy couch, facing a fire pit with flames visible. The setting transitions from warm sunset hues to deep blue in the sky, while the calm waters of Lake Winnebago reflect the evening light.

Cottage in Fond du Lac

4.99 out of 5 average rating, 282 reviews

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

Top guest favorite

A wooden pier extends over calm water, leading towards the horizon where sunlight reflects off the lake's surface. An American flag is displayed atop a pole at the end of the pier, contributing to the serene lakeside setting.

Cottage in Fond du Lac

4.92 out of 5 average rating, 131 reviews

The Beach House

Cute year round home with fantastic evening sunsets on the East shore of Lake Winnebago. Enjoy the lake life with this 3 bedroom, 1.5 bath, private beach and pier, located on a private beach road and a close drive to restaurants in the surrounding area. Ideal for Walleye Weekend, EAA Convention, Road America, Green Bay Packer games, Wisconsin Badger games, Milwaukee Brewer games, Ryder Cup and more

Guest favorite

Home in Neenah

5 out of 5 average rating, 11 reviews

Rickers Bay Lake house

Your modern lakefront getaway is just a few clicks away. Whether you're seeking to unwind by the waters edge, embark on exciting aquatic adventures, or simply create unforgettable memories with your friends and or family, this lake house retreat promises an amazing experience. Book your stay now and allow yourself to be swept away by the absolute magic of lakeside living.

Superhost

A charming lakefront property is presented, featuring a well-kept dock extending into the water. Lush green trees frame the yard, while the main building exhibits a light exterior and a welcoming porch. The expansive lawn offers space for outdoor activities.

Cottage in Fremont

4.73 out of 5 average rating, 30 reviews

Lana's Lodge

Fishermans dream. Located in the heart of Fremont. Fish off your pier, bring your boat and explore the wolf river chain where you can travel for hours each direction. Your family will be close to everything when you stay at this centrally-located place. It's a 2 min walk to town with restaurants, taverns and ice cream shop.