Holiday rentals in Plainfield

Beautiful Spanish style Home (w/inground pool)

Experience a mix of old and new at this recently renovated Spanish style villa. Casa Dra’eh – less than an hour from Chicago! Staying for business or leisure, this stylish retreat offers the perfect blend of sophistication and comfort. Relax on the private rooftop balcony overlooking the backyard , featuring a pool and veranda ideal for dining. Cook in the chef’s kitchen or unwind in modern Spanish decor. With Chicago just a short drive away, enjoy the best of both worlds. Book your stay today!

Lockports Famous Hideaway ~ 2bdrm Guest House Flat

A history buff’s dream filled with antiques & artifacts relating to Lockport, Chicago, Joliet, I & M Canal & "Route 66"! If you have roots in Illinois or Lockport, the Hideaway is for you! The entire upstairs 1,500 sq ft vintage 2 bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Family & Business Friendly. Private-entrance/self-check-in. *Can accommodate up to 6 guests. Extra charges apply after 2 guests. Have a 'historic' stay at the "Hideaway"

*The Belltower Haven*Large*Family Friendly*Wi-Fi

Our remodeled spacious apartment is located on Plainfield Road, minutes away from 1-80 & 1-55. Near: Rialto Theatre, Haley Mansion, Jacob Henry Mansion, Train Station, College of St. Francis, Joliet Junior College, Slammers Minor League Baseball and St. Joe's Hospital, New Lenox Sports Complex Minutes away from: Chicagoland Speedway, Hollywood Casino, Lewis University and Silver Cross Hospital. 30 minutes from Chicago 3 br (3 Queens beds 1 queen sleeper sofa, queen air mattress), 1 full bath

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Nice, Private Ranch Home

Nice private ranch home in a quiet neighborhood. Fox River and the river bike trail are only 3 minutes away, Rush Copley Medical Center, lots of shopping and dining options within minutes, Phillips park zoo, and water park very close, major roadways to Chicago. 10 min, from downtown Aurora where you can find the Hollywood Casino, Paramount theatre, many shopping stores and you can enjoy a walk along the Fox river, Fox valley mall and the Chicago premium outlets mall are only 20min away.

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

The Loft-Rustic Retreat and Sauna

This unique space features a beautiful relaxing yard space and easy walking distance to downtown Oswego.. If you need a place to work quietly or stay overnight this is the ideal location to get rest and relaxation, as well as, enjoy the local tranquilities. Antique shopping, River adventures, Bike trails, and more! The Fox River Trail is a few blocks from the Loft and goes North all of the way up to Algonquin. Along the trail is the River where you can tube, kayak, canoe, fish…

Odd Fellows Retreat

The history of the Odd Fellows can be celebrated in this unique retreat space. An efficient apartment for one or two guests to experience the downtown Plainfield area. There are so many restaurants within walking distance. A gourmet's delight! Begin your day with coffee from the shop downstairs. Everything you need to relax is included in this quaint 1 bedroom space. Our location is only 35 minutes from Chicago for those that want more adventure!

Less is more! Pet friendly Tiny Home near Chicago!

Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome