TOP 30 Best Lakeside vacation in Wisconsin

SpiritView Lakeside is a charming lakeside bar and restaurant located at 1426 Wisconsin 32 in Three Lakes, Wisconsin. Situated on the shores of a picturesque lake, this institution offers a relaxing and scenic dining experience for visitors. With a menu featuring delicious food and refreshing drinks, guests can enjoy a meal while taking in the beautiful views of the water. Whether you're looking for a casual meal with friends or a romantic dinner for two, SpiritView Lakeside is the perfect spot to unwind and enjoy the natural beauty of the Wisconsin countryside.

Lakeside Motel is a charming lodging establishment located at 1706 Lake Shore Drive West in Ashland, Wisconsin, United States. Situated right on the shores of Lake Superior, this cozy motel offers breathtaking views of the lake and a peaceful atmosphere for guests to relax and unwind. The rooms are comfortable and well-appointed, with all the amenities needed for a comfortable stay. Guests can enjoy easy access to the lake for swimming, fishing, and other water activities. Lakeside Motel is the perfect destination for a tranquil getaway in the heart of nature.

Lakeside Haus is a premier real estate and travel agency located at 11001 Forest Drive in the picturesque town of Presque Isle, Wisconsin, United States. Our team of experienced professionals are dedicated to helping clients find their dream lakeside property or plan the perfect vacation getaway. Whether you're looking to buy or rent a lakefront home, cabin, or condo, Lakeside Haus is here to provide expert guidance and personalized service. Let us help you make your lakeside living or vacation dreams a reality at Lakeside Haus.

The Copperwood Condominiums - Hiller Vacation Homes is a stunning real estate and travel agency located at 4516 Copperwood Circle in Eagle River, Wisconsin. Our luxurious condominiums offer the perfect getaway for those looking to relax and unwind in a beautiful natural setting. Whether you're looking for a weekend retreat or a longer vacation, our expert team is here to help you find the perfect rental property to suit your needs. With top-notch amenities and a prime location, The Copperwood Condominiums - Hiller Vacation Homes is the ideal choice for your next escape.

Northwoods Vacation Rentals is a premier real estate and travel agency located in the picturesque town of Saint Germain, Wisconsin. Situated at 1624 Shields Road, our institution offers a wide range of vacation rental properties, from cozy cabins to luxurious lakefront homes, perfect for a relaxing getaway in the Northwoods. With our personalized service and attention to detail, we strive to make your vacation experience unforgettable. Whether you're looking for a peaceful retreat or an adventurous outdoor escape, Northwoods Vacation Rentals has the perfect property for you. Book your dream vacation today and discover the beauty of Northern Wisconsin.

Dollar Lake Retreat Vacation Rental is a real estate and travel agency located at 1315 East Dollar Lake Road in Eagle River, Wisconsin, United States. This charming lakeside retreat offers a perfect blend of vintage Northwoods cabin charm and modern luxuries. Situated just steps away from the water's edge, guests can enjoy breathtaking sunsets, the soothing sounds of loon calls, and a peaceful atmosphere. The beautifully restored lake house features three fireplaces, a chef's kitchen with Viking range, game room, cozy bedrooms, and a spacious patio with a gas grill and fire pit. Guests can also take advantage of the large pier, swim dock, water toys, and pontoon rental available on site. Conveniently located just 5 minutes from downtown Eagle River, Dollar Lake Retreat is a haven for outdoor enthusiasts. The property is adjacent to snowmobile trails, near boat launches on the Eagle River Chain of 28 Lakes, and close to hiking opportunities in the Nicolet National Forest. The area is also known for hosting events like The USA Hockey Pond Hockey National Championships and the Subaru Winter Experience. Whether you're looking to relax by the lake, explore nature, or engage in water sports, Dollar Lake Retreat offers a memorable vacation experience for all seasons.

Eagles Bluff Vacation Home is a newly completed 3400-sf chalet located on 20 acres of private woodland on the south shores of Lake Content in Saint Germain, Wisconsin. This luxury home is perfect for multi-generational families and large groups looking for a peaceful and enjoyable vacation or retreat up north. With a private dock giving you access to 1880 acres of the Big St Germain Lake chain, there are plenty of opportunities for fishing, boating, and swimming. You can also enjoy an acre of shallow sandy waterfront for family fun or relaxation in the sun. For outdoor enthusiasts, the Heart of Vilas County 52-mile paved bike trail is located at the end of the driveway, along with hiking opportunities on the property and at the nearby Awassa Nature Preserve and Hiking Trail. Snowmobile enthusiasts can access the Bo-Boen trail directly from the driveway. After a day of activities, relax by the firepit areas in the front yard or down by the shore.

Lake Tomahawk Vacation Rentals is a premier lodging destination in the charming town of Lake Tomahawk, Wisconsin. Situated at 7323 Bradley Street, this institution offers a wide range of vacation rental options for visitors looking to experience the beauty of the Northwoods. As a real estate and travel agency, Lake Tomahawk Vacation Rentals provides top-notch customer service and expert guidance to help guests find the perfect accommodation for their stay. Whether you're seeking a cozy cabin by the lake or a spacious vacation home for the whole family, this institution has something for everyone. Book your stay with Lake Tomahawk Vacation Rentals and make unforgettable memories in this picturesque lakeside community.

Northern Haven Vacation Rentals of Door County is a real estate and travel agency located at 6664 Wisconsin 57 in Baileys Harbor, Wisconsin, United States. We offer some of the most beautiful vacation rental properties in Door County, known for its stunning scenery, charming villages, dining options, and recreational activities. Our dedicated team is always ready to cater to your needs and provide you with a delightful home-away-from-home experience. With over a decade of experience, we offer round-the-clock access to our office and maintenance support network, ensuring a stress-free vacation experience. Come stay at our waterfront property in Jacksonport, with a wooded lot and accommodations for up to 10 guests (no pets allowed). Book your trip with Northern Haven Vacation Rentals for a truly unforgettable vacation in Door County, Wisconsin.

Our Lakeside Legacy House is a charming lodging option located at 8104 Wisconsin 57 in Baileys Harbor, Wisconsin. Situated right by the tranquil waters of Lake Michigan, this institution offers guests a peaceful and scenic retreat. The house boasts a legacy of providing top-notch hospitality and comfortable accommodations for travelers seeking a relaxing getaway. With its picturesque surroundings and cozy atmosphere, Our Lakeside Legacy House is the perfect destination for those looking to unwind and reconnect with nature. Whether you're looking for a romantic escape or a family vacation, this institution promises a memorable and rejuvenating experience for all who stay.

Jackson's Lakeside Cottages is a charming lodging option located at 1180 Jackson Lane in Saint Germain, Wisconsin, United States. Situated right by the serene lake, this institution offers cozy cottages for a relaxing getaway. Whether you are looking for a weekend retreat or a longer vacation, Jackson's Lakeside Cottages provides a comfortable stay with picturesque views. As a real estate agency, they also offer opportunities for those interested in purchasing their own lakeside property. Additionally, their travel agency services can help you plan the perfect vacation in this beautiful area. Experience the beauty of the Wisconsin Northwoods at Jackson's Lakeside Cottages.

Bear Paw Vacation Homes is a premier real estate and travel agency located in the picturesque town of Eagle River, Wisconsin. Our team specializes in providing luxurious vacation homes for rent in the area, offering guests a comfortable and unforgettable stay. Whether you are looking for a cozy cabin in the woods or a waterfront retreat, we have the perfect property to suit your needs. Situated at 5241 Dam Lake Road, our agency is dedicated to helping you find the ideal vacation rental for your next getaway in the United States. Experience the beauty of Eagle River with Bear Paw Vacation Homes.

Thompson's Lakeside Cabins is a charming travel agency located at 6470 South Bluebird Road in Lake Tomahawk, Wisconsin, United States. Offering cozy and well-appointed cabins right on the lake, this institution provides the perfect getaway for those looking to relax and unwind in nature. With breathtaking views, modern amenities, and a friendly staff ready to assist with any travel needs, Thompson's Lakeside Cabins is the ideal destination for a peaceful and rejuvenating vacation.

Rogers' Retreat Eagle River Vacation Home is a stunning lodging option located at 1434 Watersmeet Lake Road in Eagle River, Wisconsin, United States. Situated along a tranquil lake, this retreat offers breathtaking panoramic views and seamlessly combines modern comfort with the peace of nature. Built in 2023, this Lake Home is perfect for families looking to enjoy the Eagle River Chain of Lakes in a quiet, peaceful setting close to downtown Eagle River. Rogers' Retreat exudes modern charm in an area filled with adventure and serenity. Guests can enjoy amenities such as a 20' Starcraft Deck Boat and a 3-person Yamaha Deluxe for weekend adventures. Explore the nearby lakes and local trails for a truly immersive experience.

Lakeside Lookout is a real estate and travel agency located at 10201 Upper Road in Woodruff, Wisconsin, United States. With 34 Arbor Vitae homes that allow dogs, you can bring your furry friend along for the trip. Make sure to check individual home listings for any limits on the number and size of dogs allowed. Additionally, 80 of our vacation rentals in Arbor Vitae offer internet access so you can stay connected throughout your stay. Our local team includes professional housekeepers who will ensure that your rental is clean and stocked with amenities upon your arrival, allowing you to simply settle in and relax. Visit Lakeside Lookout for a seamless and enjoyable vacation experience in Arbor Vitae.

Elite Lake Vacation Rentals is a family-owned and locally operated real estate and travel agency located at 672 West Main Street in Lake Geneva, Wisconsin. We specialize in providing newly renovated and modern vacation rentals in Southeast Wisconsin, offering a variety of choices from lakefront houses to secluded wooded homes. Our goal is to help our guests create lifelong vacation memories in beautiful surroundings. Whether you are looking for a downtown city retreat or a peaceful retreat in nature, we have the perfect vacation rental for you. Our friendly and knowledgeable reservation agents are available to assist you in finding the ideal home that fits your needs. With our No Worry guest experience, we strive to make your stay as stress-free and enjoyable as possible.

Geneva Lakes Vacations is a real estate and travel agency located at 326 Center Street in Lake Geneva, Wisconsin, United States. Our properties are fully stocked with essential supplies to make your stay comfortable and convenient. There are no keys to return or desks to visit - simply lock the door behind you at the end of your stay. Join our program to learn how owning a vacation home can be both easy and profitable. Receive information on vacation rentals in Southeastern Wisconsin, as well as new property alerts, special offers, and amazing properties. Experience the beauty of Lake Geneva with Geneva Lakes Vacations.

Hazel's Hideaway is a charming vacation rental located at 414 Baker Street in the picturesque town of Lake Geneva, Wisconsin. This cozy retreat offers a peaceful and relaxing atmosphere for guests looking to escape the hustle and bustle of everyday life. The property features comfortable accommodations, modern amenities, and a convenient location near the town's attractions and activities. Whether you're seeking a romantic getaway or a family vacation, Hazel's Hideaway is the perfect home base for your Lake Geneva adventure. Book your stay today and experience the beauty of this lakeside retreat.

Neshonoc Lakeside Campground is a peaceful retreat nestled along the shores of Neshonoc Lake in West Salem, Wisconsin. This beautiful campground offers a variety of accommodations, including cozy cabins, spacious RV sites, and tent camping areas. Guests can enjoy swimming, fishing, and boating on the lake, or simply relax and take in the stunning views of the surrounding nature. The campground also features a playground, hiking trails, and a camp store for all your needs. Whether you're looking for a family-friendly getaway or a serene escape into the great outdoors, Neshonoc Lakeside Campground has something for everyone.

Seagull Bay - A Lakeside Motel is a charming lodging institution located at 325 South 7th Street in Bayfield, Wisconsin, United States. Offering a perfect getaway with stunning views of Lake Superior, Seagull Bay combines old-school charm with modern design. Guests can experience a laid-back and quiet escape in the picturesque town of Bayfield. The motel provides a relaxing environment where guests can unwind and enjoy the beauty of the lake. With comfortable accommodations and easy access to the Brownstone Trail, Seagull Bay is the ideal place to leave your worries behind and immerse yourself in the tranquility of the surroundings. The property features three unique locations - Seagull Bay Motel, Bay West, and The Brownstone Cottage - each offering direct access to the lake and the opportunity to explore the charming town of Bayfield. Whether you're looking for outdoor adventures, local events, or simply a peaceful retreat, Seagull Bay is the perfect destination for your Bayfield getaway. The owners, Isaac and Mollie, are dedicated to providing a welcoming and peaceful atmosphere for guests to enjoy. Book your stay at Seagull Bay and experience the best that Bayfield has to offer. Contact us today to plan your unforgettable vacation.

Wells Lakeside Cottages is a charming lodging institution located at W4926 County Road G in Mauston, Wisconsin, United States. Nestled by the lakeside, this cozy retreat offers a peaceful and picturesque setting for guests to relax and unwind. The cottages are well-appointed and provide all the comforts of home, with stunning views of the lake just steps away. Whether you're looking for a romantic getaway or a family vacation, Wells Lakeside Cottages is the perfect destination for a memorable stay in the beautiful Wisconsin countryside.

Lakeside Motel is a charming lodging establishment located at 210 Wisconsin Dells Parkway in the picturesque town of Wisconsin Dells, Wisconsin, United States. Situated right by the tranquil waters of a beautiful lake, this motel offers guests a peaceful and relaxing stay with stunning views of the surrounding natural scenery. The comfortable rooms are equipped with all the necessary amenities for a comfortable stay, and the friendly staff are always on hand to assist with any needs or questions. Whether you're looking for a romantic getaway, a family vacation, or just a peaceful retreat, Lakeside Motel is the perfect choice for your next stay in Wisconsin Dells.

Spider Lake Lakeside Retreat is a charming lakeside property located at 7720 South Spider Lake Road in Iron River, Wisconsin, United States. This institution serves as both a real estate agency and a travel agency, offering a variety of vacation rental options for those looking to escape to the serene surroundings of Spider Lake. With stunning views, cozy accommodations, and a range of outdoor activities available, Spider Lake Lakeside Retreat is the perfect destination for a relaxing getaway in the heart of nature. Whether you're looking to buy or rent a lakeside property, or simply wanting to plan your next vacation, this institution has everything you need to make your stay unforgettable.

#1 Lakeside is a premier real estate and travel agency located at 657 Fort Road in the picturesque town of La Pointe, Wisconsin, United States. Specializing in lakefront properties and vacation rentals, #1 Lakeside offers a wide range of options for those looking to explore the beauty of the area. Whether you are in search of a dream vacation rental or looking to buy your own piece of paradise, #1 Lakeside is your go-to destination. With a team of experienced agents and a commitment to exceptional customer service, #1 Lakeside is the perfect choice for all your real estate and travel needs in the stunning lakeside community of La Pointe.

Duncan Road Vacation Rental is a charming lodging establishment located at 1437 Duncan Road in Bloomer, Wisconsin, United States. This institution offers a variety of vacation rental properties for travelers looking to explore the picturesque surroundings of Bloomer. Whether you are looking for a cozy cabin, a spacious home, or a lakeside retreat, Duncan Road Vacation Rental has the perfect accommodation for your stay. With a team of experienced real estate and travel professionals, guests can expect personalized service and expert guidance in finding the ideal rental property for their needs. Book your stay at Duncan Road Vacation Rental and experience a relaxing and memorable vacation in the heart of Wisconsin.

Lake Port is a charming vacation rental located in Pepin, Wisconsin, offering a peaceful retreat for those looking to escape the hustle and bustle of city life. Situated on the shores of Lake Pepin, guests can enjoy stunning views of the water and surrounding nature. This real estate and travel agency offers a range of rental options to suit every traveler's needs, from cozy cabins to spacious lakefront homes. Whether you're looking for a romantic getaway or a family vacation, Lake Port has something for everyone. Book your stay today and experience the beauty of Wisconsin's countryside.

Lakeside Terrace is a charming institution located at 4938 Bay Drive in Superior, Wisconsin, United States. This picturesque property offers a variety of accommodations including lodging options, real estate services, and an RV park. Situated by the serene waters of the lake, Lakeside Terrace provides a peaceful and relaxing environment for guests to enjoy. Whether you are looking for a cozy place to stay, interested in buying or selling real estate, or seeking a spot to park your RV, Lakeside Terrace has something to offer for everyone. Experience the beauty of lakeside living at Lakeside Terrace in Superior, Wisconsin.

Waters Edge Lakeside Cabins is a charming lodging facility located at 701 Division Street in Stoddard, Wisconsin, United States. Situated right on the water's edge, this institution offers cozy cabins with stunning views of the lake. Whether you're looking for a relaxing getaway or a fun-filled adventure, Waters Edge Lakeside Cabins is the perfect place to stay. As a real estate agency, they also offer opportunities for those looking to purchase their own lakeside property. Additionally, their travel agency services can help you plan the perfect vacation in this picturesque location. Experience the beauty of lakeside living at Waters Edge Lakeside Cabins.

Villa Del Lago Vacation Rental is a charming lodging establishment located at 100 Pine Street in Pepin, Wisconsin, United States. Situated near the picturesque Lake Pepin, this vacation rental offers stunning views and a peaceful atmosphere for guests to relax and unwind. The property features comfortable accommodations, modern amenities, and easy access to outdoor activities such as boating, fishing, and hiking. Whether you're looking for a romantic getaway or a family vacation, Villa Del Lago Vacation Rental is the perfect destination for your next trip to Wisconsin.

Olympia Vacation Owners is a small timeshare located in the heart of Wisconsin's Lake Country, offering one, two, and three bedroom units that are fully furnished and equipped with modern amenities. The property is currently undergoing major construction for the Olympia Fields and Olympia Hills projects, which will bring new apartments, condos, shops, restaurants, and more to the area. Guests can enjoy outdoor activities such as biking, hiking, fishing, and swimming in the beautiful lakes nearby. Conveniently located near I-94, Oconomowoc provides easy access to both Madison and Milwaukee for a variety of entertainment options. Please note that the bathrooms in our units do not have walk-in showers, but all units have a shower over tub setup. Come stay with us and experience the charm of Lake Country in Wisconsin!