Holiday rentals in Osceola

5 out of 5 average rating, 23 reviews

Flat in Kewaskum

Local Landmark / Coffeehouse / Kettle Moraine

One-of-a-kind, newly renovated, turn-of-the-century Coffee Corner Suites, located at the "Gateway to the Kettle Moraine- Northern Unit". Just step out your door and into the iconic Coffee House. West Bend -- 5 minutes, Foundry 45 -- 3 minutes, Lomira -- 15 minutes Rest easy knowing we have thought of everything to make your stay worry-free! King bed, full kitchen, keyless entry, heated towel bars, and on-site laundry. PRO TIP: We provide a progressive length of stay discount! SAVE MORE

4.99 out of 5 average rating, 274 reviews

Cabin in Elkhart Lake

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

4.98 out of 5 average rating, 130 reviews

Home in Glenbeulah

Stay at Sunrise LLC, Like being at Grandma's

Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural area, recreation trail head is 3 miles east of us as is the Wade House, 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. We do not have WIFI Phone reception for Internet is good. No Cable or Satellite TV, Over 32 antenna channels. Smoking is allowed outside of the home. No pets allowed.

Campervan/Motorhome in Glenbeulah

4.8 out of 5 average rating, 20 reviews

Secluded Country Farm Getaway

Experience the best of both worlds at Bear Lake Ranch—where peaceful forest trails meet vibrant farm life, all in one unforgettable stay. Wander private hiking paths through Bear Lake and the Kettle Moraine State Forest, and enjoy the charm of a working farm. Just 15 minutes from Road America and Plymouth, 8 minutes to fishing and fun at Dundee’s Long Lake, 25 minutes to Kohler and Lake Michigan, and 45 minutes to EAA. Horse trailers, bikes, and boats are welcome. Relax, explore, and reconnect.

4.68 out of 5 average rating, 19 reviews

Cabin in Campbellsport

Peaceful Lakeview Cabin Stay On Private Pennisula

Tucked on a private peninsula in Wisconsin’s Kettle Moraine, Birchwood Log Cabin is a quiet 4-bedroom, 2-bath retreat with stunning lake views and space for up to 14 guests. Enjoy a wraparound deck, wood-burning fireplace, and open-concept great room for cozy nights in. While our lake is view-only, you’re just a short walk to Kettle Moraine Lake’s public beach, boat launch, and vibrant Tiki Bar. Come for the stillness, stay for the trails, sunsets, and connection. Open year-round. Pets welcome!

4.64 out of 5 average rating, 311 reviews

Flat in Plymouth

Pineyard Plymouth Apartment

Enjoy this older upper floor apt. with two single bedrooms with a twin bed in one and a full bed in the other, full bath, kitchen, living room, and off street parking. VCR/DVD player and internet is available. Kitchen is equipped with dishes, pots, pans, stove, and refrigerator. We are five minutes from Road America, fifteen minutes from Sheboygan, and thirty minutes from Fond du Lac. Only three blocks from downtown Plymouth enjoy many shops and eating establishments. Pets are NOT allowed.

4.95 out of 5 average rating, 77 reviews

Cabin in Campbellsport

Fraser Fir Rustic Cabin near Lake w/ Sunset Views

Take time to slow down in this timeless cabin on Kettle Moraine Lake. In the summer, enjoy quiet moments watching the sun set from the front porch, then relax by the fire pit under a sky full of stars. Fish from the dock, kayak around the lake, or bring your boat to soak up the sun. In the winter, grab your ice-skates or ice-fishing gear and head out on the lake. With countless trails nearby, the hiking options are limitless and beautiful in every season. Your next adventure awaits.

4.71 out of 5 average rating, 107 reviews

Barn in Sheboygan Falls

Quiet Country Charm

Cozy barn loft with rustic charm. This newly renovated private loft sleeps 4 with the possibility of 1 or 2 more if you don’t mind sleeping on an air mattress. This room includes a bathroom with shower and small efficiency kitchen with microwave, coffee maker, and small refrigerator. The futon pulls out to a double bed. This relaxing local comes complete with barnyard animals for an authentic Wisconsin experience! You won’t forget the peaceful surroundings of this rustic destination.

5 out of 5 average rating, 146 reviews

Cabin in Cascade

hot tub and sauna on 5 private acres

Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your inspired getaway awaits!

4.97 out of 5 average rating, 210 reviews

Home in Plymouth

Wyatt's Country Home - King Bed

Soak up the modern vintage charm of our fully remodeled and updated home! Thank you for choosing our sparkling clean space. Our home is nestled on two quiet acres just north of Plymouth in the peaceful country. Enjoy coffee as the sun rises from one of the two decks, or perhaps a cocktail by the fire as the sun sets. We ourselves lived in this home for our first 5 years and turned it into a beautiful and peaceful space for ourselves that we would now like to share with everyone.

4.99 out of 5 average rating, 178 reviews

Home in Campbellsport

Gleason's Chouse

You'll love staying in our unique home, in a quiet neighborhood. This is a recently remodeled 1867 church converted to a "Chouse". Featuring 2 bedrooms, Full Kitchen, 1 Bathroom, Balcony, Parking, and a Gazebo.. all beautifully complimented by a range of antiques and decorations. 8 Miles East of Hwy 41, a 45 min drive to Oshkosh or an hour to Milwaukee. Just down the from Lake Bernice & Eisenbahn Bike Trail. Also close enough to the Kettle Moraine Forest to hike and sightsee!

4.97 out of 5 average rating, 101 reviews

Chalet in Campbellsport

Long Lake Chalet

This recently remodeled and tastefully furnished, PET FRIENDLY, cabin boasts a unique charm. Nestled along the shores of Long Lake in the heart of the Kettle Moraine Forest, this lakefront property offers 45’ of serene, peaceful beauty. This stunning home features a large yard, pier access and year round recreational activities. Disconnect, unwind and take in all that Kettle Moraine has to offer. Whether vacationing with family or friends this retreat is waiting for you.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Osceola holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Osceola

Place to stay in Plymouth

4.98 out of 5 average rating, 86 reviews

The Loft at Hickory Haven-A Modern Rural Studio

CarrieRating, 5 stars3 weeks ago

Hickory Haven lived up to its name! The surroundings are beautiful and the loft was pristine! This is the cleanest airbnb I have stayed in - everything was perfect. Our host, Mary, left several special touches like fresh fruit and local cream to make us feel right at home. This place is truly an oasis.

Private room in Glenbeulah

4.96 out of 5 average rating, 49 reviews

Rooms at the Mill - Dillingham Suite

KyleRating, 5 stars3 months ago

Very beautiful surroundings and amazing building! My stay was absolutely perfect! A must stay if in the area!

5 out of 5 average rating, 46 reviews

Private room in Cascade

Suite Retreat - Hideaway in the Woods ❤

DonnaRating, 5 stars2 weeks ago

We usually don’t book rooms within a home, but with limited options during a busy race weekend at Road America, we tried this place—and it was a pleasant surprise! The suite is spacious, clean, and comfortable, and having coffee and cream provided was a thoughtful touch. Mike and Katie were awesome hosts—friendly, helpful, and full of local suggestions. The location was perfect too—just 15 minutes from the track. Would definitely stay again!

5 out of 5 average rating, 16 reviews

Flat in Port Washington

Mariner's Point Carriage House

DanRating, 5 starstoday

We had a lovely stay in such a charming place! Lori and Michael are so attentive to details that make this a memorable stay that feels like home. When we had issues with WiFi reception, they bought and installed a booster within an hour! We highly recommend The Carriage House to anyone needing a place to stay in Port Washington.

4.92 out of 5 average rating, 13 reviews

Private room in Plymouth

Stoney Acres

RobinRating, 5 stars2 weeks ago

We had a wonderful 1 night stay at this lovely, quiet place. Set in a beautiful Kettle Morraine countryside, the accommodations were clean, comfortable and cute. We enjoyed the horse and kitties nearby and our visit to Elkhart Lake for the day.

4.86 out of 5 average rating, 184 reviews

Private room in Plymouth

A Bit of the "Lake" right in Town

JulietteRating, 5 stars3 weeks ago

Easy check in. The accommodations were spacious, comfortable, and clean. The neighborhood was very quiet and safe with great walking areas. Thank you!

4.93 out of 5 average rating, 54 reviews

Private room in Kewaskum

Condo in the Kettle Moraine

KevinRating, 5 stars1 day ago

A fantastic place to stay, with a spacious bedroom and even roomier private bathroom. The grassland view out the bedroom window was very pleasant, and a ceiling fan helped keep us very comfortable as we slept. Jackie was super friendly and her dog also greeted us as we came inside. A fantastic location, quiet place to sleep, driveway parking, nothing more we could ask for.