Holiday rentals in Winnebago

4.95 out of 5 average rating, 118 reviews

Hip-N-Colorful Prospect Smoke Free

Excited to offer this space to travelers! We have fun with some color. Queen bed in the first bedroom, XL twin beds in the back bedroom. Great location! Close to stylish, revitalized downtown Rockford with terrific restaurants, night life, shops, and galleries. Upper unit in vintage 4 family with long term tenants below and I live in the other upper. Absolutely no parties. Only registered guests. No smoking inside or outside on the property. Violation results in $500 cleaning fee/poor review

4.96 out of 5 average rating, 240 reviews

Cottage in Rockton

Country Farm Cottage

Cozy farmhouse Country Cottage on a historic private farm setting. Safe, quiet, peaceful space to relax. Minutes to golfing, hiking, antiques, canoeing, camping, parks, or use as writers retreat. Rockton has great shopping & dining, 20 min to trendy eateries in Beloit WI. Close to local wedding venues Wineries 25 min away May- Nov: orchards cider & donuts Child friendly Visit our Goats Wifi & Roku TVs No Smoking inside No Pets Farm animals and pets on the farm Host lives on same farmstead

Farm stay in Cherry Valley

4.97 out of 5 average rating, 365 reviews

Bed and Breakfast with Horse Hotel at VRR

Victory Reigns Ranch Horse Hotel and Bed and Breakfast boasts a beautiful ranch setting close to Deer Run Forest Preserve, Oak Ridge Forest Preserve and other equestrian trails. *Come with or without your horse. We also have an RV hookup if needed along with spacious trailer and RV parking. *If interested in horse boarding during your stay a 12 x 12 barn stall is $35 per night. Private pasture turn out available for $25 per horse per night. Trailer hook up is $35 per night per trailer.

Place to stay in Brodhead

4.97 out of 5 average rating, 159 reviews

Historic Randall Schoolhouse

You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

4.9 out of 5 average rating, 119 reviews

Fun Retro Apartment in Downtown Rockford

Close to all the action, you are steps away from top restaurants, night life, theaters, sports and the river. Freshly updated space with an extra touch of all things we love 80's, you will find an Atari 5200 with favorites like Pac Man along with your favorite VHS tapes like Breakfast Club and Sixteen Candles. We have a dedicated work area in second bedroom. Great for a quick trip or long work stay. Located steps from Abreo Restaurant, all guests receive 10% discount during stay

4.97 out of 5 average rating, 33 reviews

Cottage in Winnebago

Relax. Recharge. Reconnect.

Need a family-friendly spot that feels like home but with a little extra fun? This midcentury gem in downtown Winnebago is cozy, stylish and ready for your next getaway. Close to all the best local spots, it’s perfect for chilling out, playing games and making memories together. What will your family’s favorite corner be? "It was warm, cozy, clean, and so quiet!" "The house has been updated, but also has some of its old charm" “Garage and EV charger were much appreciated!”

4.93 out of 5 average rating, 547 reviews

Flat in Edgewater

Upscale Urban Retreat 1 bedroom, ground Floor

Charming and beautiful ground floor; wood floors and original woodwork. Secure keypad entry. Owner on adjoining premises. Minutes to Indoor Sports Factory, downtown nightlife, restaurants, shops, Japanese Gardens, Rockford Art Museum, Nicholas Conservatory and Sinnissippi Gardens.. 5 blocks to river and rec path. Centrally located quiet Edgewater Neighborhood District. Ideal for business travelers, couples, solo adventurers and more. High speed internet.

4.96 out of 5 average rating, 181 reviews

Cabin in Oregon

GOOSE ISLAND CABIN -Secluded Riverside Eco-Retreat

Nestled along the banks of the Rock River under tall oaks, ye ol cabin was built by early settlers in 1907. Legit rustic charm. Secluded yet only 10 mins from the fun town of Oregon. 100 acres of private property, bordering Lowden-Miller State Forest. Includes use of canoes/kayaks, large riverfront yard, grills, hammocks, deck, porch and firewood. $35/night/person/pet after first 2 people. Message Tim about accomodating big groups and events.

4.95 out of 5 average rating, 437 reviews

Bungalow in Rockford

Arts and Crafts Bungalow with Outdoor Space

We welcome you to a centrally located two-bedroom Arts & Crafts Bungalow. Ideally situated near sports venues, shopping, museums, and restaurants, the house is a perfect place for families, professionals, and couples. We have free on street parking in front of the home, We are 10 minutes away from the UW Sports Factory, Anderson Japanese Gardens, and Nicholas Conservatory. We are 20 minutes away from Anna Page Park and Rock Cut State Park.

4.83 out of 5 average rating, 29 reviews

Guest house in Rockford

2 My cozy sweet home

Kick back and relax in this calm, stylish space. Perfect place to relax after work. This is a guest small duplex house semi-attached to the main home. We are located near the Lowes Distribution Center, the Chicago-Rockford International Airport, about 20-minute drive to the Byron Plant, and about 6-to-8-minute drive to downtown Rockford, Discovery Center, Coronado Theatre, BMO Center, and about 12 minutes away from Swedish American Hospital.

5 out of 5 average rating, 10 reviews

Guest house in Rockford

Shelby’s garden cottage.

Shelby’s cottage has been part of Bluffs on the bend farm for over 65 years. It has undergone a complete overhaul and update with all the modern conveniences while retaining a country cottage charm. It is the perfect getaway for a couple. The location is next to the historic ( originated in 1924 ) Kilbuck Bluffs Forest Preserve. While being nestled in the country it is centrally located to restaurants , bars and shopping.

4.94 out of 5 average rating, 370 reviews

Loft in Rockford

510 Studios Loft East

Beautiful, newly updated one bedroom loft apartment in busy downtown area. Just steps to restaurants, shopping and entertainment. Gorgeous decor, new furnishings with couch, love seat, dining table and extra comfy king size bed. Bathroom is completely remodeled. Very fun and artsy style, full size kitchen, large outdoor deck, cable TV, Neflix and more! Great place to stay for business and for pleasure in the heart of Rockford.

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 Winnebago holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Winnebago

4.61 out of 5 average rating, 46 reviews

Aesthetical Loft

Mrs.DicksonRating, 5 stars1 month ago

I really enjoyed staying here was very comfortable and easy to access the host was super great no complaints and I will stay again and it’s definitely recommended if you like high ceilings and beautiful surroundings and also the shower was top tier wonderful it’s private nice space to get a peace of mind and for longer stays

5 out of 5 average rating, 19 reviews

Flat in Freeport

Walk everywhere in downtown Freeport.

LukeRating, 5 stars1 week ago

A fantastic price for a convenient location! The inside is spacious with all the amenities you could need. The outside can look a bit uninviting, but the room itself, as well as Judy, were fantastic!

Home in Rockford

4.63 out of 5 average rating, 159 reviews

Experience Our Relaxing Riverhouse

JessicaRating, 5 stars1 month ago

If we come back to Rockford, we would definitely stay at this location agian! So beautiful, relaxing, affordable wmin a great private location.

5 out of 5 average rating, 11 reviews

Home in Rockford

Charming Pet-Friendly Rockford Escape

LaVonnaRating, 5 stars2 days ago

My stay at Michelle's home was very peaceful. Great neighborhood and the home was very well kept with extra amenities such as the work out area. I loved that my family could stay in a home and felt like we were at home. Highly recommended and the host is easy to work with and very informative.

Flat in Edgewater

4.86 out of 5 average rating, 36 reviews

Upscale apartment in Rockford!

EboneeRating, 5 stars2 days ago

It was everything we needed. The home was exactly like the pictures. We had our two kids under six and our dog. It was perfect. They had room to play and we had space also. I took my dog on a walk around the block and our kids loved the Park!! I would absolutely stay here again!

5 out of 5 average rating, 5 reviews

Charming 2 bedroom Apartment

HuuquocRating, 5 stars2 weeks ago

the building look old but the room is nice and clean, the kitchen and bathroom are new and We ve got everything for a nice and comfortable stay. Thanks Jhonathan,