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Oshkosh vacation rentals

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Top-rated vacation rentals in Oshkosh

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Rental unit in Green Bay

4.89 out of 5 average rating, 106 reviews

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

Two bedroom upper apartment in downtown Green Bay. 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! PLEASE NOTE: 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

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.

Cabin in Princeton

4.97 out of 5 average rating, 213 reviews

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.

Home in Oostburg

4.98 out of 5 average rating, 183 reviews

River Ridge-HOT TUB, Games, Luxury, 8 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.

Home in Sheboygan

4.94 out of 5 average rating, 190 reviews

Beachfront getaway in Sheboygan

One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun. The open kitchen, dining and living room is full of light from the sliding glass doors on the back of the house, which access a deck and a large back yard. Upstairs is a spacious loft with a pull out couch. Fire pit in the back yard. Just steps from a playground at King Park. Amazing sunrises, worth waking up for.

Home in Oostburg

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...

Cottage in Fond du Lac

4.98 out of 5 average rating, 249 reviews

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.

Rental unit in Manitowoc

4.84 out of 5 average rating, 113 reviews

Manitowoc Northshore retreat

Charming Newley remodeled upstairs bungalow Located blocks from Lake Michigan marina, in the heart of the city. Walking distance to museums, eateries, microbrews and wineries, , irishpubs, beaches. Car ferry, fitness centers, zoo, walking and biking trails, many golf courses. 41 miles to Packer stadium and hall of fame. 26 miles to Kohler American club, spa, and golf courses. Road America Elkart Lake is 26 miles. Door county 59 miles.

Home in Sheboygan

4.97 out of 5 average rating, 135 reviews

Lake Michigan home with gorgeous views!

Our beautiful lakefront home is perfect for bringing everyone together - Ladies weekend, guys golf trip, family reunion, Packers games...this is your place. Minutes to downtown Sheboygan/Kohler, with 5 star PGA championship golf courses (Black Wolf Run, Whistling Straits, The Bull of Pinehurst), Kohler Waters Spa, and the beaches/dunes of Kohler Andrae State Park. Renovated bedroom and movie room completed early 2020.

Home in Sheboygan

4.97 out of 5 average rating, 129 reviews

Lakeview Beach Bungalow - With outdoor Hot Tub!

Beautifully updated beach house just one block off of Lake Michigan. Beautifully landscaped backyard with pergola and 6 person Hot Tub! Watch the sunrise and sunset from the second floor master balcony. Walk to the lake 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. Massive bathroom with deep soaking tub.

Condo in Sheboygan

4.98 out of 5 average rating, 132 reviews

Downtown Beachside Condo with Lake Michigan Views

You will see & hear the beauty of Lake Michigan during your stay at this main floor condo. 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.

Home in Poynette

4.98 out of 5 average rating, 122 reviews

It's the "After Summer" at Beach Garden Bungalow!

Oooh, look! Here’s an awesome cottage right across the street from the Wisconsin River - Kayak heaven!! Relaxation and “re-creation” are what you’ll find here with plenty of fresh air, sunshine and river views. The home is located on nearly an acre of land with open yard space to stargaze by the fire pit as well as mature trees perfect for bird, deer, woodchuck and squirrel watching from the patio.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Oshkosh vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Oshkosh's top sights

EAA Aviation Museum89 locals recommend

Paine Art Center and Gardens54 locals recommend

Fox River Brewing Company Waterfront Restaurant43 locals recommend

Menominee Park Zoo38 locals recommend

Becket's35 locals recommend

Outlet Mall station29 locals recommend

Other great vacation rentals in Oshkosh

Cabin in Wautoma

4.83 out of 5 average rating, 40 reviews

Whispering Pines on Deer Lake in Wautoma

Home in Waupaca

4.91 out of 5 average rating, 35 reviews

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

Home in Manitowoc

4.9 out of 5 average rating, 31 reviews

Brick Vacation House in Manitowoc, WI

Home in Green Bay

4.94 out of 5 average rating, 50 reviews

Lakefront Boho Cottage

Home in Appleton

4.98 out of 5 average rating, 63 reviews

Sleeps 27! Gorgeous Getaway with Pool/Hot tub!

Home in Wautoma

4.96 out of 5 average rating, 50 reviews

Silver Lake Home with Up North Panoramic Views

Home in Waupaca

4.87 out of 5 average rating, 79 reviews

Wistful Vista on Stratton Lake House Only

Cottage in Montello

4.98 out of 5 average rating, 49 reviews

Tranquil 2 Bedroom Getaway on Private Lake

Quick stats about vacation rentals in Oshkosh

Total rentals
820 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
7.6K reviews
Family-friendly rentals
640 properties are a good fit for families
Pet-friendly rentals
230 properties allow pets
Rentals with a pool
40 properties have a pool

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Oshkosh?
Yes! Work meets play with ease at over 310 vacation rentals in Oshkosh featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Oshkosh?
Four-legged friends are welcome in Oshkosh. Choose from more than 230 vacation rentals for guests traveling with pets.
Are there Oshkosh vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Oshkosh, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly apartment rentals in Oshkosh?
Oshkosh has more than 40 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in bed and breakfast rentals in Oshkosh?
Experience the best of Oshkosh with our bed and breakfast rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Oshkosh have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Oshkosh. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oshkosh have a bbq area?
Absolutely! We offer over 210 house rentals with a bbq area in Oshkosh. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oshkosh have a gym?
Absolutely! We offer over 90 house rentals with a gym in Oshkosh. Enjoy a tailored experience with all the comforts you desire.
Do bed and breakfast rentals in Oshkosh have air conditioning?
Absolutely! We offer over 10 bed and breakfast rentals with air conditioning in Oshkosh. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Oshkosh?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 70 homes with wifi, over 70 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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