
Holiday rentals in Diamond
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Top-rated holiday rentals in Diamond
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Dog Approved Country Suite
This floor of my home is all yours! Non-shared studio, non-smoking property, fully fenced back yard. Please choose my home for yourself, not just your dog; enjoy a full kitchen & appliances, 1 full size futon bed, cable (basic) tv, laundry & bath. It’s peaceful living on a septic w/well water. Welcome to the country! Clean yes, but lived in & loved. Limited WiFi-no streaming. Weekly & monthly discounts. Approx 5 miles to I80 & 21 miles to Starved Rock. LOOK AT A MAP I can’t change my location.

Starved Rock Retreat w/hot tub & full-fenced yard!
2-bedroom, 1-bathroom pet-friendly townhouse with fenced yard in a quiet neighborhood close to everything. Ideal for couples, yet comfortable for all travelers. Safe, private, and well-suited for remote work. Enjoy an open floor plan and a new patio with a year-round hot tub & seating area. Fully fenced yard with a 6-ft vinyl privacy fence is exclusively yours. No pet restrictions. Includes in-unit laundry and two bedrooms - one set up as an office/workout space. Peaceful and made for unwinding.

Lyle and Taylor present-Spacious Private Apt -
Beautiful spacious apartment perfect for long term work assignments or travelers who want all the comforts of home. Sleeps up to 5; King, Queen + sofa Amenities abound: ~FREE WiFi ~2 smart TVs w/HBO, SHOWTIME, Cinemax, 144 cable channels, Netflix ready (with your account) ~Full kitchen with fridge/gas stove/dishwasher/microwave/toaster oven/Keurig ~FREE washer & dryer with basic supplies ~Bathroom w/shower/tub combo ~Non-smoking ~Complimentary weekly cleaning/linen laundry for extended stays

The Garden House - Murals and more
Our garden-themed house🌿 located on busy Plainfield Road is minutes away from 1-80 & 1-55. Near: Rialto Theatre, Haley Mansion, Jacob Henry Mansion, Joliet Union Station, College of St. Francis, Joliet Junior College, Slammers Minor League Baseball & St. Joe's Hospital. Minutes from: Chicagoland Speedway, Hollywood Casino, Lewis University & Silver Cross Hospital. 30 min. Southwest of Chicago. 🏡Entire house: 2 Bdr (2 Bd & 1 Futon), Bathroom (new shower), Living Room, Kitchen, Front Deck

Cathy's Little Farm Loft
Cathy's Little Farm loft is a 500 sq ft apartment inside a storage barn on a wooded country acre. Fully appointed two story space offers peace and quiet. It is located close to I57, Walmart, Community College, Airport, Fair Grounds, National Guard Training Center, 15 minutes from Olivet, 60 miles south of Chicago. King size bed and twin size sofa sleeper upstairs, full size sleeper sofa in living room. Well equipped full size kitchen and laundry. Large lawn, gardens, and chickens to enjoy.

King Bed • Luxury Boho Studio • City Chic Haven
✤City Chic Haven✤ is a luxury studio in downtown Kankakee, steps from the train station, taverns, and walkable attractions. Enjoy a cozy king bed, fast Wi-Fi, free coffee/tea bar, stocked kitchen, & 55” smart TV for a relaxing or work friendly stay. ✶ Across the street from the Kankakee train station ✶ Walkable to local cafes, axe throwing & taverns ✶ 0.3 Miles to St. Mary's Hospital ✶ 1.3 Miles to Riverside Medical Center ✶ 2.9 Miles to Olivet Nazarene University ✶ 55 Miles to Midway Airport

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.

Two king beds with 3 bedroom 2 bath
4 minutes from I-57 expressway. This is a three bedroom two full bath townhome with a 2 car attached garage. King bed & 55' smart tv in the master bedroom. The Master bedroom also has a full bathroom with complimentary body wash, shampoo & conditioner. 2nd bedroom has a king size bed with king size hotel pillows. 3rd bedroom has queen bed with 55" smart tv. In closet you will find a deluxe queen size air bed with extra pillows & linens. Patio has table & chairs & charcoal grill.

Get Your Kicks in Our Cozy Cottage Near Route 66
Enjoy all the comforts of home when you have to be away. Our fully furnished cottage is located 4 miles from Rt 53 / Historic Rt 66 and just blocks from the Kankakee River. Just 5 minutes to "downtown" Wilmington featuring restaurants, a wine bar, a local brewery, and multiple antique stores. ✧ Easy access to everything that Joliet has to offer just 20 miles away, including the Autobahn and Route 66 Raceway. ✧ 7 miles to easily access I55 for a quick ride into Chicago.

"You're invited" Suitcase Required
The whole group will enjoy easy access to everything from this centrally located place. Head to our many state parks, take a boat ride down the Illinois River, be adventurous and skydive at Skydive Chicago and the list goes on. This two-bedroom 1 bath house welcomes you with all the amenities to feel right at home. Sleeps 3 adults comfortably. (1-Queen Bed and 1 full size bed) It has a fully stocked kitchen. washer/dryer and outdoor seating/dining.

Cheerful 2 bedroom home near Rt. 66
Soak up the hometown charm with a relaxing and tranquil stay in historic Wilmington near the Kankakee River. You won't be living in a van down on the river during this stay. You'll enjoy a warm, cozy home that's near shopping, flavorful restaurants and picturesque sunsets on the Kankakee River. This two bedroom home can accommodate up to six people. The kitchen and living room feature an open concept for more intimate or a night with close friends.

“The remote retreat”
We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!
Popular amenities for Diamond holiday rentals
Other great holiday rentals in Diamond

A-frame Cabin w/Jacuzzi & Pickleball Court

Fox River House

Downtown Modern Studio by Route 66

River View House with Large Deck and Game Room!

Cozy Cabin on the farm, with hot tub & fire pit!

Starved rock area Beautiful country ranch

Cozy Clean Updated - Parking - Washer/Dryer

1 Bed w/ Full Kitchen A Mile From Downtown Oswego
Destinations to explore
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- Guaranteed Rate Field
- Matthiessen State Park
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- University of Chicago
- DuSable Black History Museum and Education Center
- Promontory Point
- National Museum of Mexican Art
- Starved Rock State Park Campground
- Frederick C. Robie House
- Cantighy Park
- Kankakee River State Park
- Illinois Institute of Technology
- Wheaton College
- The Promontory
- Chicago Premium Outlets
- The Morton Arboretum
- Harrison Park




