Search Vacation Homes in Gillespie

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3
In one month
Aug 15 - Aug 17
In two months
Sep 12 - Sep 14

Vacation Homes in Gillespie

Edwards House; Litchfield, IL; Pets welcome
Cozy retreat with a neatly made bed, two bedside tables, and a light-colored rug.

Edwards House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (17)
"Mike and Amy have a beautiful cozy place to stay. My partner and I had a wonderful time and were super comfy during our stay!"
$159 nightly
The price is $168
Aug 1 - Aug 2
Total includes taxes and fees
Edwards House; Litchfield, IL; Pets welcome
Harrison House; Litchfield, IL; Pets welcome
Detached garage with a small porch area and a wooden staircase leading to a deck.

Harrison House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (11)
"We loved the house, plenty of space and it was furnished with everything we could need. Highly recommend!"
$175 nightly
The price is $185
Jul 16 - Jul 17
Total includes taxes and fees
Harrison House; Litchfield, IL; Pets welcome
Chestnut House; Litchfield, IL; Pets Welcome
Enjoy cooking in this well-equipped kitchen with microwave and oven, stainless steel sink, and ample cabinetry.

Chestnut House; Litchfield, IL; Pets Welcome

9.0 out of 10, Wonderful, (7)
"The house was very nice and we had a relaxing stay. We will definitely consider staying here again if we stay in the area."
$164 nightly
The price is $173
Jul 27 - Jul 28
Total includes taxes and fees
Chestnut House; Litchfield, IL; Pets Welcome
State Street House; 3-br house; PETS WELCOME; Litchfield
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, wooden countertop, and dark backsplash.

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

10.0 out of 10, Exceptional, (6)
"My daughters, son-in-law and I found ourselves needing to stay near Hillsboro for my Grandmother’s funeral. Mike and Amy were gracious hosts. We truly felt the love they have for the home. It’s a great location, a quick walk to downtown Litchfield. I highly recommend!"
$215 nightly
The price is $221
Jul 17 - Jul 18
Total includes taxes and fees
State Street House; 3-br house; PETS WELCOME; Litchfield
Plainview Vineyard Retreat by StayLage
Welcome to the charming Fasting Room of Plainview Vineyard, featuring a traditional design with a cozy porch and a unique wine bottle sculpture.

Plainview Vineyard Retreat by StayLage

2.0 star property
$433 nightly
The price is $457
Jul 15 - Jul 16
Total includes taxes and fees
Plainview Vineyard Retreat by StayLage
The Carlinville Cottage
Enjoy cooking in the well-equipped kitchen with stainless steel appliances and ample counter space, plus a convenient island for extra workspace and seating.

The Carlinville Cottage

10.0 out of 10, Exceptional, (11)
"This was a fantastic stay in a wonderfully clean space! We really enjoyed Carlinville cottage ans would stay again!"
$490 nightly
The price is $501
Jul 22 - Jul 23
Total includes taxes and fees
The Carlinville Cottage
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free