Diamond Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Diamond

NEW Spacious and Comfy Duplex - 55" & 50" Smart TVs, Workspace, Cul-de-sac
9.0 out of 10, Wonderful, (2)
"The neighborhood is great, very nice house with very firm beds. Thank you"
NEW Spacious and Comfy Duplex - 55" & 50" Smart TVs, Workspace, Cul-de-sac
Events Welcome! 10-Acre 12,000SF Chicagoland Private Estate w/ 2 Pools & 2 Lakes
9.6 out of 10, Exceptional, (5)
"We had a ball everything was good the house was lit 🔥 thank yall so much"
The price is NZ$3,775
per night
12 Jun - 13 Jun
Events Welcome! 10-Acre 12,000SF Chicagoland Private Estate w/ 2 Pools & 2 Lakes
King Bed, DIsney+, Spacious, Family-Friendly House
10.0 out of 10, Exceptional, (17)
"It was clean and nice and quiet"
The price is NZ$674
per night
12 Jun - 13 Jun
King Bed, DIsney+, Spacious, Family-Friendly House
Save an average of 15% on thousands of hotels when you're signed in
Renovated luxury villa with 7 bedrooms 5 bathrooms. Located on 40 acres of land.
9.8 out of 10, Exceptional, (13)
"This home is beautiful and Nora was so friendly and helpful throughout the process. We would all absolutely stay there again! We were able to comfortably accommodate our 20 guests with no issue."
Renovated luxury villa with 7 bedrooms 5 bathrooms. Located on 40 acres of land.
Yellow house near the railroad tracks in Coal City
The price is NZ$487
per night
13 Jun - 14 Jun
Yellow house near the railroad tracks in Coal City
Cozy two bedroom home by historic Rt. 66, pet friendy too!
10.0 out of 10, Exceptional, (1)
"The owners have so many thoughtful things tucked throughout the home to make your stay pleasant. From plug in scents to fluffy bathrobes, we were impressed with their attention to details. We were happy to find this rental in small town Wilmington and will be returning."
The price is NZ$369
per night
10 Jun - 11 Jun
Cozy two bedroom home by historic Rt. 66, pet friendy too!
Cozy 3-bedroom home on the waterfront, dog friendly!
10.0 out of 10, Exceptional, (19)
"This was the perfect spot for our family. Everything was clean and beautiful. The kiddo loved going up into the loft area. We loved looking at the river. If we’re ever back in Illinois, this is where we will stay!"
Cozy 3-bedroom home on the waterfront, dog friendly!
Plainfield Home w/ Game Room Near Harrah’s Casino!
10.0 out of 10, Exceptional, (1)
"Everything about this stay was easy and pleasurable. The home was comfortable, very clean and perfect location for our needs. Check in and out was effortless"
Plainfield Home w/ Game Room Near Harrah’s Casino!
Rural Seneca House w/ Yard Near I-80
8.6 out of 10, Excellent, (4)
"The Pros: The property was comfortable and clean. The Cons: The keypad for the door was confusing and difficult to use. We ended up getting locked out in the dark for almost 15 minutes because it took 12 tries to get it to unlock, and it had a 10-minute lock-out after 10 failed tries. The kitchen is woefully under-equipped. The cooking and serving implements as sparse and mismatched. It was very difficult to prepare and serve meals. When we checked in there were only two towels in all the...
Rural Seneca House w/ Yard Near I-80
Cozy Cottage Just 5min→Historic Route 66
9.4 out of 10, Exceptional, (8)
"I was in town for work, and this place was great! Very clean, and cozy. Couldn’t have asked for anything better."
The price is NZ$427
per night
12 Jun - 13 Jun
Cozy Cottage Just 5min→Historic Route 66
Beautiful Peaceful 3 Bedroom Home in Plainfield
8.6 out of 10, Excellent, (7)
"Came to town for 4th of July week to visit family. Rental was close to family. The rental was clean and had all the amenities. Only recommendation would be for ceiling fans in each room."
Beautiful Peaceful 3 Bedroom Home in Plainfield
3 Bedroom Family Friendly Haven
3 Bedroom Family Friendly Haven
Rural Seneca House w/ Yard Near I-80
3.5 star property
10.0 out of 10, Exceptional, (1)
"Excelente me gustó muchísimo la recomiendo 💯 está espaciosa y lo principal segura y muy tranquilo la volveria a rentar muchas gracias."
Rural Seneca House w/ Yard Near I-80
Cozy1bed with large private fenced yard, Brisbin Rd I-80, Short to Long-term
Cozy1bed with large private fenced yard, Brisbin Rd I-80, Short to Long-term
Plainfield Home w/ Game Room Near Harrahs Casino!
3.0 star property
Plainfield Home w/ Game Room Near Harrahs Casino!
Stunning Mazon Home w/ Fishing Pond & Patio!
10.0 out of 10, Exceptional, (4)
"The house was really spacious for the 12 of us to stay at. We really enjoyed all of the games that the house came with. The land is absolutely beautiful and we had space to set up outdoor sports as well. Overall, we had an unforgettable weekend at the ranch!"
Stunning Mazon Home w/ Fishing Pond & Patio!
1 Acre newly remodeled Coal City home
1 Acre newly remodeled Coal City home
New Construction, Full High-end Duplex 3 bd 2.5 Ba
New Construction, Full High-end Duplex 3 bd 2.5 Ba
Just a Small Getaway in Joliet
Just a Small Getaway in Joliet
Rosewood Apartments
2.0 star property
Rosewood Apartments
Don't see what you're looking for?
See all available properties in Diamond
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Diamond you may be interested in

aruba- la cabana beach resort and casino
aruba- la cabana beach resort and casino
Super 8 by Wyndham Joliet
2.0 star property
8.2 out of 10, Very good, (262)
"Good hotel"
The price is NZ$168
per night
9 Jun - 10 Jun
Super 8 by Wyndham Joliet
Red Roof Inn Chicago - Joliet
2.0 star property
6.6 out of 10, (1007)
"For price it was a good stay no frills hotel "
The price is NZ$110
per night
1 Jul - 2 Jul
Red Roof Inn Chicago - Joliet
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Diamond holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Diamond. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Diamond. Seeing all the best attractions is bound to make you fall in love with Diamond. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Diamond short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Diamond?

Yes, there are holiday rentals close to the most popular sights in Diamond, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Diamond has to offer?

Events Welcome! 10-Acre 12,000SF Chicagoland Private Estate w/ 2 Pools & 2 Lakes: This holiday home rental outside of Diamond is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a pool table.

What’s there to see and do in Diamond?

While exploring the area, visit family-friendly sights like Richard Petty Driving Experience, or get outside and enjoy nature at Midewin National Tallgrass Prairie. In the wider area, you’ll find Grundy County Speedway and Kankakee River State Park.

What’s a holiday rental in Diamond like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Diamond. Holiday rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a family getaway.

Recent reviews of Diamond properties
Expedia verified reviews