
Cottage vacation rentals in Oshkosh
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Top-rated cottage rentals in Oshkosh
Guests agree: these cottages are highly rated for location, cleanliness, and more.

Sandalwood Cottage - 300 Feet From Lake Michigan
A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

Charming Country Cottage
Located on a quiet country road, our quaint little cottage is a lovely place to unwind, make memories, and embrace the simpler life. Featuring an open concept first floor with a cozy living space, an electric fireplace, and a well stocked kitchen. We have been working hard to create a comfortable and inviting atmosphere. Important: the cottage is located next to our home on 5 acres, if you are looking for seclusion, keep looking. We are a large work at home family. You will see and hear us.

RiverFront Cottage>Private Pier>Firepit & Wildlife
Cute little cottage located right on the Fox River overlooking the peacefulness nature has to offer. Enjoy your very own private dock as well as 200 feet of river frontage surrounded by tall mature trees. Be submerged by the community of fishermen (& women) located on Puckaway Lake, surround yourself with wildlife, or paddle down the Fox River. Soak up the sun on the dock or learn how to build the best fire in the fire pit! The adventure is all around you! Which one will you be choosing?

Nostalgic Lakehouse with Ferry Pontoon & Hot Tub
This thoughtfully restored 1960s cottage sits on peaceful Spring Lake: perfect for swimming, fishing, and creating nostalgic memories lake with your family. Outside you'll enjoy a beautiful private backyard with a hot tub, paddle/solar-powered pontoon boat, yard games, fire pit, fishing poles, and dock. Inside you'll make lifelong nostalgic memories with the huge selection of 1980/90s video games, Goosebumps books, board games & VHS films. Centrally located in an activity-filled area of WI!

Waterfront cottage with tower and hot tub!
This charming cottage is an ideal respite for your family holiday to the one-of-a-kind Green Bay, Wisconsin! Look forward to exploring this historic city, visiting iconic museums, and experiencing the vibrant Packers culture. The vacation rental home sits right on the water - offering fantastic views of the bay - and is just 10 miles from downtown. After the day's adventures, return to this cozy 3-bed, 1.5-bath house and unwind as your furry friends or children play in the waterfront yard!

Pet Friendly Antique Schoolhouse with Fenced Yard
Pond Lily is truly a unique stay; a historic schoolhouse among tranquil surroundings. Beautiful traditional craftsmanship meets all the comforts of a modern home. Pet friendly with a fenced yard. A well-stocked kitchen makes for easy home-cooked meals. The layout is ideal for small groups looking to enjoy a peaceful getaway. Snuggle up by the wood-burning fireplace in the cold months or enjoy the firepit in the warm weather. For the outdoorsman, public lands are 5 minutes away.

Morris Lake Summer Cottage
Fully renovated, sun-filled, open concept, super clean cottage is located on the northern shore of beautiful Mount Morris chain of lakes. This 163 acre chain of 5 lakes affords endless opportunities to swim, kayak, paddle board or fish. Water skiing and tubing are allowed only on the largest of the lakes, but there are plenty of quiet, no wake hours for fishing or a relaxing boat ride. Included are 2 kayaks, paddle board, and a rowboat with a trolling motor. . .

Cottage on the Pond - Big Green Lake
Our place is good for couples, solo adventurers, families, and furry friends (dogs limit 2 $50 fee). Enjoy the peace and beauty of the pond (sorry, no fishing) while just across the street from beautiful Green Lake. Lots of room outside for the kids to roam. Easy walk to the beach. (see satellite map picture). There is a public launch nearby and plenty of room to keep your boat on the side lawn. Hiking trails, White River Marsh, and Fox River are all nearby.

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.

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.

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

Milk House Cottage
Once a small barn, now a unique guest house surrounded by trees and nature. A secluded setting, yet right on the edge of the city and in close proximity to three colleges. Not far to Fond du Lac Loop bike and walking trail. Also close to grocery stores and great restaurants. Explore the nature area on the property! Out of consideration of all guests NO pets are allowed.
Popular amenities for Oshkosh cottage rentals
Cottage rentals with a hot tub

Lakeside Living-Sleeps 17-Wautoma

CJ's Cozy Cottage

Dockside Cottage @ Evergreen Campsites & Resort

Fall on the lake: hot tub, firepit & cozy nights
Pet-friendly cottage rentals

Pine Grove Hideaway

Private 3 bedroom lake house

Fox River Runaway

Lakefront Cottage with Sandy Shore & Sunset Views

Charming Lakeside Cottage

3BD/Sleeps 8 - cozy cottage + lake view and access

Up North Lake Escape

Tranquil 2 Bedroom Getaway on Private Lake
Private cottage rentals

Quaint Channel Cottage

Crooked Wood Cottage

Lake Poygan Cottage where you can Fish Hunt Ride

Pack Manor

Cozy Year Round Lake Poygan Cottage

Lana's Lodge

Charming cottage located on a peninsula! Peaceful!

Lake View Cottage near Public Boat Launch
Quick stats about cottage rentals in Oshkosh

Total vacation rentals
Explore 10 vacation rentals in Oshkosh

Nightly prices starting at
Oshkosh vacation rentals start at ﺩ.ﺇ441 per night before taxes and fees

Verified guest reviews
Over 350 verified reviews to help you choose

Wi-Fi availability
10 of Oshkosh vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oshkosh rentals

4.8 Average rating
Oshkosh stays are highly rated by guests—averaging 4.8 out of 5!
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- Kohler-Andrae State Park
- Whistling Straits Golf Course
- The Golf Courses of Lawsonia
- Bay Beach Amusement Park
- West Bend Country Club
- Trout Springs Winery
- The Bull at Pinehurst Farms Golf Course
- Pine Hills Country Club
- Oneida Golf Club
- Pollock Community Water Park
- Sunburst
- Vines & Rushes Winery
- Kerrigan Brothers Winery
- Little Switzerland Ski Area
- Blackwolf Run Golf Course