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13 Large Vacation Rentals That Sleep 20 or More in Illinois

Big groups often find it challenging to book convenient accommodations together and find themselves getting multiple hotels in different areas of town. Fortunately, there are some excellent vacation rental properties in cities across Illinois that keep your entire group in one place and that come with all the comforts of home.

If you are planning a family reunion, friends gathering, or business event in Illinois, here are some Airbnb and Vrbo properties that are perfect for large groups.

Grafton Getaway, Dow Enjoy the farm life for your big event
Credit: Enjoy the farm life for your big event by Vrbo.com

Grafton Getaway, Dow

The Grafton Getaway is a farmhouse on 23 acres of secluded land in Illinois. With 3,900 square feet of space, it has eight bedrooms, 12 beds, and 2.5 bathrooms to accommodate up to 21 people. You’ll be on a hobby farm here with chickens, ducks, a walking trail, and fishing available. The hosts have two other properties available for rent too. Features of this rental include a trampoline, ping pong table, classic record player, complimentary coffee and tea, smart TVs, Wi-Fi, and kids’ zone in the barn. Up to two pets of any size can stay here.

Three Pines Petersburg, Petersburg An Italianate mansion perched up on a hill
Credit: An Italianate mansion perched up on a hill by Airbnb.com

Three Pines Petersburg, Petersburg

Three Pines is an Airbnb vacation rental home that was built in 1875 and has been restored while still retaining its vintage splendor. The home can sleep at least 20 guests and has 10 bedrooms, 16 beds, and eight bathrooms. It’s an Italianate mansion perched up on a hill and with 3.5 acres of outdoor space to enjoy around the seating areas and fire pits. If you need even more space, there’s a separate suite attached via breezeway that can sleep five more people. Up to two dogs, up to 50 pounds are welcome here with your group when you get pre-approval and pay an extra fee. The home is located about a half-mile from the town square.

Four-Bedroom and Five Bedroom Homes, Galena Territory One of the rental houses you can stay at here
Credit: One of the rental houses you can stay at here by Vrbo.com

Four-Bedroom and Five Bedroom Homes, Galena Territory

With this Illinois group rental property, you’ll get a four-bedroom house and a five-bedroom house that are next to each other. Together, the homes sleep up to 22 people and have nine bedrooms, 11 beds, nine full bathrooms, and two half baths. It’s a nice place to be if you want a little separation among your group and to be in the Galena area, which offers everything from antiquing to cross-country skiing, wineries, and boating. Guests can also use the new recreation center nearby, which has an outdoor pool, kids’ pool, indoor pool, fitness center, and activity room.

Spectacular Fulton Market Penthouse, Chicago Plenty of stylish, open space to spread out
Credit: Plenty of stylish, open space to spread out by Airbnb.com

Spectacular Fulton Market Penthouse, Chicago

Up to 24 people can stay at this Airbnb rental that features six bedrooms, 14 beds, and four bathrooms in Chicago. This property is actually two side-by-side designer apartments in the West Loop neighborhood. You’ll be on the top floor of a historic 1920s building and have open living spaces and upscale furnishings inside. Guests also have stocked kitchens and bathrooms, as well as in-unit laundry machines.

Lodge at the Brixen Ivy Ranch, Galena Territory Lovely lake views from here
Credit: Lovely lake views from here by Vrbo.com

Lodge at the Brixen Ivy Ranch, Galena Territory

Groups wanting to be near Galena and up to 20 people can stay in this 10,800-square-foot lodge that has eight bedrooms, 15 beds, and eight bathrooms. If you have more than 22 people, you can add on a rental of the separate, nearby guest house to accommodate a total of 30 people. Perks of staying here at the lodge are impressive stone fireplaces, three kitchens, and a wrap-around deck that looks out over 300 acres of rolling hills. Head outside to the llamas, miniature horses, and other animals on your way to the trails and two bass fishing ponds.

Massive Five-Bedroom Waterfront Cabin Getaway, Dixon Massive Five-Bedroom Waterfront Cabin Getaway
Credit: Massive Five-Bedroom Waterfront Cabin Getaway by

Massive Five-Bedroom Waterfront Cabin Getaway, Dixon

Situated on 12 acres of land, this is a 4,200-square-foot, two-story home available to rent in Dixon, Illinois. It has five bedrooms, 18 beds, and 3.5 bathrooms to accommodate up to 26 people. The list of amenities provided here includes a trampoline, soccer field, wrap-around deck, recreational table games, TVs, and Wi-Fi. This unique property also comes with four kayaks, three canoes, fishing pools, and awesome riverfront views. When you stay here, you’ll also be just five minutes from downtown Dixon to check out the shops and restaurants.

Lovely Nine-Bedroom Mansion, Chicago Lovely Nine-Bedroom Mansion
Credit: Lovely Nine-Bedroom Mansion by Vrbo.com

Lovely Nine-Bedroom Mansion, Chicago

Up to 21 people can stay in this Chicago Vrbo rental that’s close to Montrose Beach and 4,200 square feet in size. It has nine bedrooms, 11 beds, and 3.5 bathrooms. You’ll be just three blocks from Lake Michigan and two blocks from the red and purple train stops. The huge rental also comes with five gated parking spots for your vehicles. Wi-Fi and cable TV are available.

Mulholland Mansion House, Nauvoo Lots of new updates in this vacation home
Credit: Lots of new updates in this vacation home by Vrbo.com

Mulholland Mansion House, Nauvoo

This 4,501-square-foot rental property sleeps up to 30 people in the heart of Nauvoo and has five bedrooms, 21 beds, and six bathrooms. The interior was refurbished in 2019 and has lots of new features to enjoy. It is a three-level home that has a great family room and kitchen for big gatherings. The oversized bunk room and large game room downstairs also make this a good rental for your group. Outside, you’ll find a large, grassy area in the yard.

Home with Themed Bedrooms for Over 50 People, Groveland Kids and the young-at-heart will love it here
Credit: Kids and the young-at-heart will love it here by Vrbo.com

Home with Themed Bedrooms for Over 50 People, Groveland

With 16 themed bedrooms and seven themed bathrooms, this 13,000-square-foot house is designed with big groups in mind. Known as Medley Manor, this large home also features a 2,000-square-foot, 50s-style dining room and a game room with a pool table, shuffleboard, air hockey, foosball, and other games. The rooms feature favorite themes and characters from Star Wars, Harry Potter, sports, and more. The home is located in a quiet and safe neighborhood that’s just a short drive from local spots. This home can actually sleep up to 55 people in the various rooms and isn’t shared with any other groups. Amenities include laundry machines, internet, TV, a fire pit, and lots of parking.

Entertainment Oasis, Rockford Keep the whole family entertained here
Credit: Keep the whole family entertained here by Vrbo.com

Entertainment Oasis, Rockford

When you want to be in the Rockford area, consider this Vrbo rental that has five bedrooms, 10 beds, and four bathrooms. Twenty people can comfortably stay here for a family retreat. There’s a seven-person jacuzzi and heated indoor pool here that both kids and adults love. You’ll also find a free-play game room with pinball machines and other arcade games. Head to the movie room with some popcorn to watch your favorite flicks.

Paradise on the Sea, Southern Precinct Many country club amenities to enjoy nearby
Credit: Many country club amenities to enjoy nearby by Vrbo.com

Paradise on the Sea, Southern Precinct

Here’s an Illinois Vrbo rental that sleeps approximately 28 people and that has 5,500 square feet of space, six bedrooms, 20 beds, and 4.5 bathrooms. The home has about a thousand feet of lake frontage and comes with kayaks and paddleboards to use. The space is spread across three levels and is on a two-acre property. If you are planning something special, the hosts can arrange wedding receptions, rehearsal dinners, business meetings, and other events at the private meeting and banquet facilities nearby. Located along the Lake of Egypt, this is a great place to be to check out Garden of the Gods and the local wineries.

Stone Mansion, Chicago Access the whole city via public transit from here
Credit: Access the whole city via public transit from here by Airbnb.com

Stone Mansion, Chicago

When you’re visiting Chicago with a big group, consider this 2,300-square-foot apartment with four bedrooms, 10 beds, and two bathrooms. The Stone Mansion sleeps up to 20 people and dates back to 1893 when it was built as a single-family home for an affluent banker. Today, the home is equipped with Wi-Fi, a fridge, bar, lots of seating, HDTVs, and nice décor. The backyard has a bistro-like area so you can get outside of the apartment for a bit if you like. Neighbors live in the apartment below this space, so you’ll need to keep noise levels down. Pets are welcome with pre-approval and a $25 per night fee.

The Nest by Beach and Lake, Bond County A great lake home for your next gathering
Credit: A great lake home for your next gathering by Vrbo.com

The Nest by Beach and Lake, Bond County

The Nest is a Vrbo rental property with six bedrooms, 38 beds, four full bathrooms, two half baths, and 3,600 square feet of space. It sleeps 30 people and is a lake house that was totally renovated inside in 2017. This light-filled home features master bedrooms and laundry rooms on each of the two floors. It also has a chef’s kitchen and four patio doors that lead out to 3,000 square feet of deck space on multiple levels. The home is hidden among the trees with lake views in each direction. This is a kid-friendly rental that allows pets too.

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