Vacation rentals in Oshkosh

4.88 out of 5 average rating, 115 reviews

A cozy fire pit is surrounded by a circle of stones, featuring neatly arranged wooden seating on either side. Vibrant green grass creates a welcoming outdoor space, while shrubs provide a natural backdrop to the setup, enhancing the relaxed atmosphere for gatherings.

Apartment in Green Bay

Up Top Downtown (7 min Lambeau) (1 min Downtown)

Two bedroom upper apartment in downtown Green Bay. **NO PETS** Walking distance to many restaurants and stores. Less than 3 miles to Lambeau Field and only 1 block from the Green Bay Metro FREE shuttle bus route to the Packer games! We have stays in 3 north eastern Wisconsin locations: Apple Core Cottage in Appleton airbnb.com/h/applecorecottage Heart of the Door Homestead in Door County, Peninsula Center airbnb.com/h/heartofthedoor Up Top Downtown in Green Bay airbnb.com/h/uptopdowntown

4.9 out of 5 average rating, 105 reviews

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

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!

4.97 out of 5 average rating, 218 reviews

An A-frame cabin showcases its sloped, maroon roof amidst tall green pine trees. A wooden deck is seen at the front, featuring seating and a grill, while a shaded umbrella stands beside a stone patio for outdoor dining.

Cabin in Princeton

A-frame in the Pines

"Up North" cabin decor with modern amenities. Cute A-frame cabin nestled amongst mature red & white pines. Outside space to run & play or relax by the campfire or fireplace inside. Chargrill available. Bring your own charcoal. Living room with TV, dining area, kitchen & pantry, bathroom, & bedroom with a queen size bed on main level. The "loft" upstairs has 2 bedrooms, 1 with 2 twin beds , & the other space with a queen size bed and a reading area that opens up to your own private balcony.

5 out of 5 average rating, 36 reviews

Home in Oshkosh

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.

4.98 out of 5 average rating, 196 reviews

A game room is highlighted by retro arcade games and vibrant wall graphics. Bright colored arcade machines, including a shuffleboard and skee ball, stand out against a dark, playful backdrop. Warm lighting enhances the inviting atmosphere for entertainment and socializing.

Home in Oostburg

River Ridge-HOT TUB, Games, Luxury-10 bed, 5 STARS

The search is over, you have found the PERFECT getaway at River Ridge South! The moment you pull in, you will become instant hero for planning the ultimate retreat. This property has something for everyone! Beautiful seclusive country home (3800 sq ft) on 4 acres of a pristine and manicured lawn with the Onion River passing through it. This home is THE perfect countryside retreat for large group gatherings with three levels of finished space and great outdoor amenities.

4.87 out of 5 average rating, 38 reviews

A spacious deck offers scenic views of the surrounding landscape and a tranquil body of water. Outdoor seating is arranged with a sectional sofa and a picnic table, inviting relaxation and gathering. Lush greenery and vibrant fall foliage frame the natural setting under a clear blue sky.

Home in Amherst

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.

4.96 out of 5 average rating, 187 reviews

A hammock is set between two trees on a grassy area, facing the serene view of Lake Michigan. A spacious guest home with large windows is visible in the background, framed by lush greenery and a clear blue sky.

Home in Oostburg

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...

4.99 out of 5 average rating, 282 reviews

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

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.

4.92 out of 5 average rating, 131 reviews

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

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

4.73 out of 5 average rating, 30 reviews

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

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.

5 out of 5 average rating, 40 reviews

A serene lakeside view displays a pebble-strewn shoreline lined with several Adirondack chairs, facing calm waters. Two floating docks are visible, adorned with orange flotation devices, and lush greenery surrounds the area, creating a tranquil natural setting.

Cottage in Cascade

Stunning Lakefront Cottage with Private Beach

Our Lakefront Cottage is a relaxing escape for nature enthusiasts and those seeking a peaceful retreat. Our newly remodeled cottage showcases modern elegance blended with cozy comfort. Our lakefront is 105 feet with crystal-clear water, perfect for swimming, fishing, and winter recreation.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

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Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Oshkosh vacation rentals

Stay near Oshkosh's top sights

Fox River Brewing Company Waterfront Restaurant43 locals recommend

Menominee Park Zoo38 locals recommend

Becket's35 locals recommend

Outlet Mall station29 locals recommend

Oshkosh Public Museum29 locals recommend

The Ruby Owl Tap Room28 locals recommend

Vacation rentals with pools in Oshkosh

5 out of 5 average rating, 15 reviews

Home in Green Bay

Next Level~100K Game Room~ Sleeps 20~ Pool~Spa

4.95 out of 5 average rating, 22 reviews

A wide aerial view of Lambeau Field captures a vibrant crowd gathered for a packed NFL game. The image showcases fans filling the stadium, with an American flag displayed prominently on the field as fireworks are seen in the background.

Home in Wisconsin

Draft Day Stay | 25 Mins to Green Bay | Hot Tub

4.94 out of 5 average rating, 17 reviews

A heated pool area features numerous guests enjoying the water, with colorful floats and toys scattered throughout. Surrounding the pool, white lounge chairs are arranged on the concrete deck. A fence encloses the area, with lush greenery visible in the background.

Cabin in Montello

The Rabbit Retreat #1

4.88 out of 5 average rating, 8 reviews

An indoor pool area features a clear water pool surrounded by a tiled border. A large screen is positioned for viewing, and sunlight streams through two windows, illuminating the space. Colorful pool toys and two lounge chairs add comfort and convenience.

Home in Newton

Country Cottage Indoor Pool HOT TUB NFL Draft ava

4.86 out of 5 average rating, 226 reviews

An indoor pool is featured, surrounded by vibrant greenery and soft lighting along the ceiling. The water’s surface reflects a calming blue hue, enhancing the spacious layout. Potted plants are placed at the corners, contributing to the serene atmosphere.

Home in Allouez

Amazing Six Bedroom Green Bay Vacation Home!!

4.97 out of 5 average rating, 33 reviews

A private outdoor space features a heated pool surrounded by a concrete patio. Lounge chairs are arranged around the pool, while a shaded pavilion offers seating. Lush greenery provides privacy, and the fenced area enhances the secluded atmosphere.

Home in Plymouth

Private Home 4 BR+2Ba, Heated Pool by Road America

5 out of 5 average rating, 4 reviews

An outdoor pool area is framed by a black fence, with several tables and chairs arranged around it. Behind the pool, a multi-story building with a green roof and multiple balconies is visible, surrounded by landscaped greenery and trees.

Villa in Elkhart Lake

First Floor Queen with Single Pull-out

5 out of 5 average rating, 49 reviews

A serene outdoor pool area is enclosed by a fence, featuring a uniquely shaped pool with clear water. Surrounding greenery includes trees and flowers, with a pathway leading to the poolside. A small shed is visible in the background, enhancing the tranquil atmosphere.

Home in Green Bay

4 BR home w/pool (lg groups) kid friendly

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Other great vacation rentals in Oshkosh

4.9 out of 5 average rating, 42 reviews

Home in Waupaca

Big Blue on QQ - 5 Br House w/ boat rental option

5 out of 5 average rating, 27 reviews

The basement fitness area features a range of exercise equipment, including weights on a rack, a treadmill, and a punching bag. A rubber mat covers part of the floor, and the space is well-lit, providing a functional environment for workouts.

Home in New Franken

Ping Pong, Pool Table, Fitness Gym, Karaoke

4.93 out of 5 average rating, 121 reviews

Cabin in Redgranite

Majestic Pines Lakeside Lodge

4.96 out of 5 average rating, 51 reviews

An outdoor deck overlooks Silver Lake, showcasing a serene sunset reflecting on the water. Two wicker chairs are positioned for viewing, accompanied by a hot tub. Lush trees frame the scene, while an American flag is visible in the background, enhancing the lakeside experience.

Home in Wautoma

Silver Lake Home with Up North Panoramic Views

5 out of 5 average rating, 7 reviews

A serene lakeside area features two comfortable chairs facing a small fire pit, surrounded by natural stone pebbles and wooden stumps. The calm water reflects the sky, creating a peaceful setting.

Guesthouse in De Pere

Guesthouse on the water 3.9 miles to Lambeau

4.81 out of 5 average rating, 64 reviews

A charming blue cottage is positioned by the lake, surrounded by vibrant autumn foliage. A wooden deck extends from the cottage, leading down to a small dock. The calm water reflects the colorful trees, enhancing the serene lakeside setting.

Cottage in Wautoma

Up North Lake Escape

4.86 out of 5 average rating, 7 reviews

A wooden dock extends into calm waters, bordered by lush greenery. A pontoon boat is moored nearby, with trees lining the shore providing a serene backdrop. The clear blue sky reflects on the surface of the water, enhancing the tranquil setting.

Home in Waupaca

The Dake Home, on The Chain of Lakes