Holiday home rentals in Illinois

UChicago Luxurious King Suite Lakefront

Sink into a pillowtop king size bed in a sunny, spacious bedroom suite w/twin bed, his/hers closets and comfy love seat. Spacious 1,000 s.f. condo luxury, kitchens /bath with granite counters, office space, 3rd-floor unit, private entrance gated and on-street parking. 1 min walk to beach, trails, golf course and bike rental. Located 1 blk from Express bus (15 minutes) to Univ of Chicago/Hyde Park and Museum of Science and Industry,(20 minutes) to Soldier Field, Grant Park, Downtown, Navy Pier

Grandma Ruby's Vintage Victorian Downstairs Suite

This historic home built in 1884 has been completely renovated with loving care by a granddaughter with fond memories of magical times at her grandparents' unique home. With ten foot ceilings and beautiful craftsmanship, this spacious downstairs unit provides a master suite with a king sized bed and a big screen TV, a large kitchen, a queen bedroom, access to a large private back yard and plenty of parking. All conveniently located to town attractions and just 5 minutes from the interstate.

The Pfaff Haus- Historic Victorian Home

Beautifully renovated historical Victorian home near downtown Pontiac, IL. This home boasts large living spaces, and three bedrooms. Your group will feel at home in this quaint and comfortable space with its 10’ ceilings and old world woodwork. The space fits 6 people comfortably. We have 3 bedrooms with queen size beds. . However we can fit up to 8 people. There is an additional charge for each person over 6 people, and we will supply two air mattresses with linens for the additional guests.

Penthouse. Historic Wicker Park. Walk | Shop | Eat

Urban Oasis. New Wicker Park Oasis Collection Launched. Brand new furnishings, beds and Decor in this prime Wicker Park location. Enjoy our intimate home with unparalleled access just steps to restaurants, boutique shops, bars & nightlife-one of Chicago's artistic & creative neighborhoods. Blue Line Train runs direct from O'Hare Airport to Downtown, Damen Stop 3 blocks away. Ambient city & train noise is to be expected in and around our home. Reserved Parking available. 1 Dog $35/night.

Rustic charm meets modern comfort at Arsulas House

Welcome to Arsula's House Sitting atop Goe Hill. Nestled in a scenic location, our property offers a cozy and inviting atmosphere with a nice blend of rustic and modern décor for an unforgettable stay. Enjoy modern amenities and a convenient location that puts you close to all of nature’s action. This property spoils you with stunning landscapes and tranquility as you explore nearby attractions and indulge in local cuisine, while you make memories to last a lifetime at Arsula's House.

Arnie’s Place, A big little space in a small town!

Take it easy at this unique and tranquil getaway. Located above a little fun popcorn shop, this place is newly renovated! Located in the heart of downtown Paxton, IL it puts you close to shopping and restaurants and 10 minutes from the Rantoul sports complex and 30 minutes from the University of Illinois Campus. Arnie’s Place is a perfect place for a couples get away, girls trip, small gatherings, a few nights stay for sporting events, a quiet place to relax and unwind.

The Gathering Place- Modern, Spacious, 6 bedrooms

The Gathering Place is a modern, spacious 6 bedroom/6 bathroom home that accommodates up to 14 people. We are family friendly and pet friendly. - 7 seat hot tub - Pool Table -Arcade games - Lightning fast Wi-Fi - 8 Smart TV's - Fully Stocked Kitchen + Coffee Bar -Yard games - Laundry - Downstairs Bar - Upstairs and Downstairs Fireplaces - < 5 minutes to owners club facility - Right across from East Golf Course - Walking trail near property - Dedicated workspace

Fall Escape | Hot Tub, Fire Pit & Galena Views

Welcome to Shenandoah Ridge—our thoughtfully designed 4-bedroom, 4.5-bath vacation rental tucked into the woods of The Galena Territory. Spacious, peaceful, and full of cozy touches to help you unwind. Whether you’re here for a family getaway, group trip, remote work retreat, or just time in nature, you’ll find everything you need to feel at home. Just 7 minutes to the Owners Club and 15 minutes to downtown Galena—close to the action, but still calm and quiet.

Aspen House - A Secluded Getaway In Nature

Relax with your loved ones at the peaceful Aspen House. A Miner's Cottage nestled in a beautiful stand of aspen trees = a quiet retreat just for you! The property is surrounded by protected wooded green space with the Taylor Run trail adjacent on the northwest side. The Owners Club, pools & lake are accessible by hiking/ 5 minute drive. Enjoy bird watching, fishing, hiking and picnicking without driving anywhere!