Holiday rentals in Oshkosh

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Top-rated holiday rentals in Oshkosh

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Guest favourite

Home

5 out of 5 average rating, 15 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

4.91 out of 5 average rating, 46 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 favourite

Home

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.

Guest favourite

Home

5 out of 5 average rating, 34 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.

Guest favourite

Cottage

4.98 out of 5 average rating, 51 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!

Superhost

Home

4.84 out of 5 average rating, 32 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

4.96 out of 5 average rating, 23 reviews

Perfect Paradise: Monthly Rates Available!

Starting 12/1/2024 Rent for an extended stay. Monthly rates until 4/1/2025 Explore your dream destination in this stunning 4-bedroom beachfront condo! With 7 beds and 3 full baths, it's perfect for relaxation. Luxurious master suite, 2-person jacuzzi tub, balcony boasting picturesque courtyard and lake views, a TV, and a gas fireplace. Convenience meets comfort with an in-unit washer/dryer and a fully stocked kitchen, providing everything you need for a seamless stay.

Guest favourite

Apartment

4.97 out of 5 average rating, 137 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.

Guest favourite

Home

4.96 out of 5 average rating, 186 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

Home

4.97 out of 5 average rating, 133 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.

Guest favourite

Cottage

4.92 out of 5 average rating, 129 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 favourite

Home

5 out of 5 average rating, 8 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.