
Holiday Homes in Illinois
Find and book unique holiday homes on Airbnb
Top-rated Holiday Homes in Illinois
Guests agree: These holiday homes are highly rated for location, cleanliness and more.

Lake Shelbyville Pond Pavilion Inn - Sleeps 6
Lake Shelbyville Pond Pavilion Inn is setting along side a stocked pond nestled in mature trees. Guests are able to fish in the pond located directly out their back door and enjoy the screened in pavilion. The Inn is 5 miles from Lake Shelbyville and all of the restaurants and shopping that goes along with it. The Inn sleep six adults and has plenty of living space for all six to stay comfortable. there are 2 full baths, and eat-in kitchen, 3 bedrooms, and a laundry room. No smoking No pets

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.

Scenic 3 bedroom Wildlife Retreat
Relax with the whole family at this peaceful place to stay. This rustic retreat is located on the Illinois river and adjacent to the 5,255 acre National Wildlife Refuge. Whether you fish, watch wildlife from the back deck, relax by firepit or go duck hunting on the bay, you are sure to enjoy this peaceful stay with your family and friends. Wildlife includes bald eagles, whitetail deer, fox, herons, egrets and over 100 species of songbirds. Native prairie trails adjacent to property as well.

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 Belden Belle: The Luxurious Chicago Townhouse
Welcome to our home! This centrally located neighborhood escape puts you right in the center of everything. You will be just minutes from major city landmarks like the Lincoln Park Zoo, the History Museum, beautiful Fullerton Beach, and some of the best dining and entertainment spots in all of Chicago. Suitable for couples, single traveling adventurer, business traveller, families (with children) and big groups. Free WiFi available. Surrounded by everything Chicago has to offer!

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!

Comfort for the entire family off of the 606
This high-capacity Airbnb can sleep up to 10 of your family and friends in the 2nd and 3rd floor unit located in our Logan Square two flat. The McCormick Tribune YMCA is right across the street along with the terminus of the 606 elevated bike/walking trail. The restaurants of Logan Square are nearby and the United Center is 15 minutes away so you can enjoy concerts and sports.

JACS COUNTRY CABINS SHAWNEE 2
COZY 1 BEDROOM, 1 BATH CABIN AT THE EDGE OF THE SHAWNEE NATIONAL FOREST. LOCATED 10 MILES FROM GARDEN OF THE GODS AND & 1 MILE FROM GLENN O JONES LAKE. IT SITS BEHIND JACS PLACE (A BAR/CONVENIENCE STORE) AND 2 MILES FROM A LAUNDRY MAT IN EQUALITY. WE PROVIDE COFFEE BUT THE CLOSEST GROCERY STORE IS ROUGHLY 10 MINS AWAY IN ELDORADO, SO PLAN, PACK SNACKS/FOOD ACCORDINGLY.
Popular amenities for Illinois holiday homes
Family-Friendly holiday homes

Comfort for the entire family off of the 606

Grandma Ruby's Vintage Victorian Downstairs Suite

Scenic 3 bedroom Wildlife Retreat

Penthouse. Historic Wicker Park. Walk | Shop | Eat

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

UChicago Luxurious King Suite Lakefront

JACS COUNTRY CABINS SHAWNEE 2

Aspen House - A Secluded Getaway In Nature
Holiday home rentals with a patio

That 70s House at Hidden Creek Estates

Glamping Near the river - 1 Bedroom Cabin

Central | BBQ Deck | Family-Friendly Pueblo Magíco

Havisham - Suite 88

One Bedroom, Victorian, Downtown Plainield

JACS COUNTRY CABINS SHAWNEE 1

Beautiful 4 bedroom Home with Game Room in Elgin

A Cosy One Bedroom with Independent Entry & Exit
Holiday home rentals with a washing machine and dryer

4-bedroom condo with 5 beds. 2 full bathrooms

Copperfield - Unit 2 - 1 Bdrm Luxury Suite - King

Historic 1840s Lamoreaux House, modern addition

two bedroom + LOFT , cozy Golf View Villa WIFI

Lakefront Home on Beautiful Duck Lake

Peaceful lakeside retreat to chillax

Stay in our cute remodeled lake farm barn home!
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