Gillespie 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 Gillespie

Route 66 house; Litchfield IL; Pets welcome
10.0 out of 10, Exceptional, (12)
"Cute little place we were visiting our grandchildren who live in the area and we all had a great time the house is well decorated so cute and everything you need is there. We will check to see if this place is available every time we visit the grandchildren."
Route 66 house; Litchfield IL; Pets welcome
Cozy loft in a small town; walking distance to the popular restaurant BG’s!
10.0 out of 10, Exceptional, (1)
"Came to Bunker Hill to visit family and needed a little more room. Cozy spot near family and restaurants. Very well stocked and comfy bed and pillows."
The price is NZ$213
includes taxes & fees
5 Jun - 6 Jun
Cozy loft in a small town; walking distance to the popular restaurant BG’s!
Harrison House; Litchfield, IL; Pets welcome
10.0 out of 10, Exceptional, (10)
"Ultra clean, very cutely decorated, and furnished with waters, clean utensils, wonderful beds, and a comfy living room arrangement. We were in town for Mother's Day and we were the envy of the family in this home! It was a lot of fun, normally a place to stay out of town is kind of a wash, you always compromise on something, but not here! If you're staying in Litchfield for whatever reason, give this house a look! Especially for the Picker's Market, every second Sunday, it's right up the road!...
The price is NZ$293
includes taxes & fees
2 Jun - 3 Jun
Harrison House; Litchfield, IL; Pets welcome
Save an average of 15% on thousands of hotels when you're signed in
The Carlinville Cottage
10.0 out of 10, Exceptional, (1)
"Beautiful newly renovated home with everything you could possibly need. Date of the art appliances and furnishings, beautifully decorated and so comfortable. We were visiting parents and family and everyone thoroughly enjoyed being together in such a great house! We will be back"
The Carlinville Cottage
Jackson House; Pets Welcome
10.0 out of 10, Exceptional, (6)
"We were there for a wedding--home was roomy and comfortable. Would stay there again."
The price is NZ$280
includes taxes & fees
5 Jun - 6 Jun
Jackson House; Pets Welcome
Edwards House; Litchfield, IL; Pets welcome
10.0 out of 10, Exceptional, (11)
"I stayed here with two large dogs while traveling daily to Springfield for an agility competition. The backyard is large and has a chain link fence. No fancy landscaping or anything that dogs could mess up, haha! There is a dog next door behind a stockade fence -- never saw it, just heard it a few times. It was not a problem for my dogs. House is perfect for one or two people. Cute and comfy. Tons of utensils and cookware in the kitchen, and condiments and water in the fridge, as well as frosty...
The price is NZ$266
includes taxes & fees
6 Jun - 7 Jun
Edwards House; Litchfield, IL; Pets welcome
Chestnut House; Litchfield, IL; Pets Welcome
9.0 out of 10, Wonderful, (2)
"The house was very nice and we had a relaxing stay. We will definitely consider staying here again if we stay in the area."
The price is NZ$278
includes taxes & fees
2 Jun - 3 Jun
Chestnut House; Litchfield, IL; Pets Welcome
Lincoln House; Litchfield, IL; Pets welcome
10.0 out of 10, Exceptional, (13)
"Proprty was well stocked for everything we could possibl y need during our stay. Clean comfortible accommodations. Host is very attentive to guests."
Lincoln House; Litchfield, IL; Pets welcome
Victorian Carlinville home on Rt. 66
10.0 out of 10, Exceptional, (7)
"Awesome place for a group of friends to relax and unwind for a few days after a particularly difficult holiday season!"
Victorian Carlinville home on Rt. 66
Kirkham Train House; PETS WELCOME
Kirkham Train House; PETS WELCOME
Lake House off Route 66
Lake House off Route 66
Spacious modernized historic home located in downtown Hillsboro.
The price is NZ$371
includes taxes & fees
3 Jun - 4 Jun
Spacious modernized historic home located in downtown Hillsboro.
The Lazy Shanty at Shale Lake #2 pet-friendly
The price is NZ$282
includes taxes & fees
5 Jun - 6 Jun
The Lazy Shanty at Shale Lake #2 pet-friendly
Historic Home near Blackburn and Square - two king beds, washer/dryer, spacious
Historic Home near Blackburn and Square - two king beds, washer/dryer, spacious
Historic Blackman-Evans Home
Historic Blackman-Evans Home
3 bedroom 2 bath sleeps 7 comfortably with the option of 9.
3 bedroom 2 bath sleeps 7 comfortably with the option of 9.
Don't see what you're looking for?
See all available properties in Gillespie
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 Gillespie you may be interested in

Baymont by Wyndham Litchfield
2.5 star property
8.4 out of 10, Very good, (978)
"We usually stay at this property twice a year and it's been pleasant as always. The hotel as well as our room was clean, the service was very friendly, and the location is very convenient "
The price is NZ$182
includes taxes & fees
1 Jun - 2 Jun
Baymont by Wyndham Litchfield
Super 8 by Wyndham Staunton
2.0 star property
8.6 out of 10, Excellent, (646)
"The room a cigarettes smoke and musty smell. The staff was very pleasant."
The price is NZ$143
includes taxes & fees
16 Jun - 17 Jun
Super 8 by Wyndham Staunton
Hampton Inn Litchfield
2.5 star property
9.0 out of 10, Wonderful, (506)
"Lovely hotel and breakfast, warm staff. I enjoyed the view of the prairie. I really wish the pool and spa had been working."
The price is NZ$212
includes taxes & fees
16 Jun - 17 Jun
Hampton Inn Litchfield
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 Gillespie 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 Gillespie. 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 Gillespie. Seeing all the best attractions is bound to make you fall in love with Gillespie. 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 Gillespie short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Gillespie?

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

What’s there to see and do in Gillespie?

While you're exploring the area, Lake Lou Yeager and Beaver Dam State Park are a couple of picturesque spots to get outside and enjoy nature. Litchfield Museum and Route 66 Welcome Center and The Winery at Shale Lake are a couple of places you'll find in the wider area.

What’s a holiday rental in Gillespie like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Gillespie. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips or small group gatherings.

Recent reviews of Gillespie properties
Expedia verified reviews