Gillespie Holiday Rentals

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Holiday Rentals in Gillespie

Edwards House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (15)
"It was exactly as the pictures showed and the host was so quick to respond to any questions. Large backyard for our fur baby and fenced in. The neighborhood was quiet. Local restaurants were really good. Looking forward to our next stay."
The price is AU$261
includes taxes & fees
8 Dec - 9 Dec
Edwards House; Litchfield, IL; Pets welcome

Lake House off Route 66

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay! The Lake House was very clean and met our needs perfectly for our weekend getaway. The property manager was always very responsive! Our dog LOVED the doggy door and the fenced area!"
Lake House off Route 66

The Carlinville Cottage

10.0 out of 10, Exceptional, (6)
"Loved the accommodations. It was great. Would definitely try to stay there again."
The price is AU$734
includes taxes & fees
6 Dec - 7 Dec
The Carlinville Cottage

Jackson House; Pets Welcome

10.0 out of 10, Exceptional, (8)
"We rent homes in one of two categories: Indulgence or Value. Indulgence we expect to pay north of $300 a night with the expectation of added amenities such as a pool, game room, luxury rooms, gorgeous view or exceptional location. The Jackson House is a value rental where our goal is to keep costs under $150 a night and the focus is on clean beds, bathrooms and decent kitchen. This house is all the above, plus it is in a quiet neighborhood, excellent TV amenities, well stocked kitchen and...
The price is AU$281
includes taxes & fees
30 Nov - 1 Dec
Jackson House; Pets Welcome

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."
The price is AU$253
includes taxes & fees
15 Dec - 16 Dec
Route 66 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 AU$271
includes taxes & fees
30 Nov - 1 Dec
Chestnut House; Litchfield, IL; Pets Welcome

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 AU$281
includes taxes & fees
8 Dec - 9 Dec
Harrison House; Litchfield, IL; Pets welcome

Victorian Carlinville home on Rt. 66

10.0 out of 10, Exceptional, (8)
"We will stay there again if we're in the area."
Victorian Carlinville home on Rt. 66

Kirkham Train House; PETS WELCOME

Kirkham Train House; PETS WELCOME

Plainview Vineyard Retreat Sleeps 8

2.0 star property
The price is AU$636
includes taxes & fees
27 Nov - 28 Nov
Plainview Vineyard Retreat Sleeps 8

Cozy studio located in small town America, Bunker Hill, IL.

10.0 out of 10, Exceptional, (6)
"Great location, felt like it was home "
The price is AU$172
includes taxes & fees
2 Dec - 3 Dec
Cozy studio located in small town America, Bunker Hill, IL.

State Street House; 3-br house; PETS WELCOME; Litchfield

The price is AU$301
includes taxes & fees
26 Nov - 27 Nov
State Street House; 3-br house; PETS WELCOME; Litchfield

Charming Hillsboro Home < 1 Mi to Downtown!

3.0 star property
Charming Hillsboro Home < 1 Mi to Downtown!

Charming Hillsboro Home < 1 Mi to Downtown!

2.0 star property
Charming Hillsboro Home < 1 Mi to Downtown!
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.
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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, (1037)
" Nice property, close to Interstate, Nice clean room."
The price is AU$145
includes taxes & fees
26 Nov - 27 Nov
Baymont by Wyndham Litchfield

Hampton Inn by Hilton Litchfield

2.5 star property
9.0 out of 10, Wonderful, (547)
"We were there one night for travel everything was fine"
The price is AU$166
includes taxes & fees
20 Dec - 21 Dec
Hampton Inn by Hilton Litchfield

Holiday Inn Express & Suites Litchfield West, an IHG Hotel

2.5 star property
9.4 out of 10, Exceptional, (475)
"Beds were lumpy, should be replaced. Other than that very nice!"
The price is AU$174
includes taxes & fees
20 Dec - 21 Dec
Holiday Inn Express & Suites Litchfield West, an IHG Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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

Our little House: This highly rated holiday home rental in Gillespie offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Gillespie?

While you're exploring the area, Beaver Dam State Park and Lake Lou Yeager are a couple of picturesque spots to get outside and enjoy nature. Litchfield Museum and Route 66 Welcome Center and Carlinville Public Square 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.