Holiday rentals in Oshkosh

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Top-rated holiday rentals in Oshkosh

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Guest favourite

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 favourite

Home in Sheboygan

5 out of 5 average rating, 20 reviews

Fairway Getaway

Welcome to our exquisite listing in Sheboygan, WI! This stunning property combines luxury, comfort, and amazing proximity to world class golf. Play a practice round on a state of the art Golf Simulator, Relax in the zen den, shuffle up and deal in the poker room, or have a movie night with family or friends on the big screen! Located near the renowned Kohler Spa, Whistling Straits, and other prestigious golf courses, this property is a haven for golf enthusiasts or a great space for Families

Guest favourite

Home in Sheboygan

4.94 out of 5 average rating, 51 reviews

3-bdrm beachfront home on Lake Mich, Sheboygan WI

3 BR. 3 BA. Fully furnished. Granite counters and stainless steel appliances in large kitchen overlooking the lake. King and Queen suites with 2nd King and full Bath. Sleeps 6, but very large sofa. Washer/Dryer. Lake Michigan views throughout, Pool table room, work space, 2 levels of patios. Sits on landscaped sand dunes and beach. 10 min drive to Black Wolf Run Golf and resort. Front row for boat races from 2 decks. Den with large fireplace. Dining table overlooking lake + lighthouse.

Top guest favourite

Home in Oshkosh

5 out of 5 average rating, 37 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.

Superhost

Cottage in Union

4.83 out of 5 average rating, 48 reviews

Southern Door CountyWaterfront Cottage/Sunsets!

Relax and enjoy the stunning water of Green Bay in Southern Door County near Shoemaker Point.Sunsets to make memories, kayak or paddle board. Cottage living 20 mins to Sturgeon Bay, restaurants, farms, hiking, boating. Close to all Door County offers yet out of the hustle and bustle. New beds, well stocked kitchen and sweeping water views. Outdoor tables for dining and comfy outdoor covered patio with sofa and firepit. Close to Titletown for the NFL draft .permit #42-56-2812-00.

Superhost

Home in Amherst

4.87 out of 5 average rating, 38 reviews

Hilltop Views & water access-20 acres!

Enjoy the amazing views from inside and outside. Includes access to kayaks, a golf cart, HOT TUB and game room! Outside fire ring and spacious deck. Trails to enjoy the outdoors & hiking. With 4 comfortable bedrooms, 3 with a queen size bed, and plenty of bunks this property easily sleeps 14 guests. The home is newly renovated with open concept floor plan & game room on the lower walk out. A full sized dining table can seat everyone. Wi-fi included with two smart TVs.

Guest favourite

Apartment in Sheboygan

4.97 out of 5 average rating, 145 reviews

Downtown Beachside Condo with Lake Michigan Views

You will see & hear the beauty of Lake Michigan during your stay at this main floor Waves of Happiness Condo hosted by Sheboygan Vacation Rentals. A deck to the north allows views of the magnificent Blue Harbor Resort. The south deck gives more amazing views of the lake, plus a park just steps out the back door. You can stroll the beach, walk the River Boardwalk, or tour our historical downtown full of shops, art, & exquisite restaurants - walkable from the condo.

Top guest favourite

Home in Oostburg

4.96 out of 5 average rating, 187 reviews

Shamba on the Lake, Oostburg, WI

Large guest home , in a rustic setting, on a peaceful 2-acre wooded lot (only 5 homes on a very private road) on Lake Michigan with a large private beach a few feet from the deck. . Magnificent panoramic view, amazing sunrises, serene twilights, magical star-studded night skies. A slice of Paradise you must experience. Located a mile from I43, 40 minutes from downtown Milwaukee, 20 mins. from golf courses in Kohler, 30 mins. from Road America in Elkhart Lake...

Guest favourite

Villa in Sheboygan

4.96 out of 5 average rating, 23 reviews

Perfect Paradise | 4BR Lakeview Condo w/ Jacuzzi

Perfect Paradise by Great Lakes Getaways! Unwind in this spacious 4-bedroom, 3-bath beachfront condo—perfect for families or groups. Enjoy a luxurious master suite with a 2-person jacuzzi tub, cozy gas fireplace, and private balcony overlooking the courtyard and Lake Michigan. With 7 beds, a fully stocked kitchen, in-unit washer/dryer, and stylish living spaces, comfort and convenience come standard. Your relaxing lakeside getaway starts here.

Guest favourite

Home in Sheboygan

4.97 out of 5 average rating, 142 reviews

Lakeview Beach Bungalow - With outdoor Hot Tub!

Beautifully updated beach house just one block off of Lake Michigan. Enjoy the newly landscaped backyard with pergola and 6 person Hot Tub! Watch the sunrise and sunset from the second floor master balcony. Walk to the lake across the street and enjoy the wind surfers and gorgeous scenery. Close to downtown and major parks. This three bedroom home will impress. Tastefully decorated. First floor laundry. Large bathroom with deep soaking tub.

Top guest favourite

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

Superhost

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.