Book Holiday Homes in Gillespie

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Featured Holiday Homes in Gillespie

Edwards House; Litchfield, IL; Pets welcome

Edwards House; Litchfield, IL; Pets welcome

Litchfield
With a stay at this vacation home in Litchfield, you'll be within a 10-minute walk of Madison Park and Litchfield City Hall.
Edwards House; Litchfield, IL; Pets welcome
The Carlinville Cottage

The Carlinville Cottage

Carlinville
The price is AU$725 per night from 7 Nov to 8 Nov
AU$725
includes taxes & fees
7 Nov - 8 Nov
When you stay at this vacation home in Carlinville, you'll be 13 minutes by foot from Carlinville Public Square.
The Carlinville Cottage
Jackson House; Pets Welcome

Jackson House; Pets Welcome

Litchfield
The price is AU$276 per night from 30 Nov to 1 Dec
AU$276
includes taxes & fees
30 Nov - 1 Dec
When you stay at this vacation home in Litchfield, you'll be on a lake, within a 5-minute drive of Madison Park and Litchfield Carnegie Public Library.
Jackson House; Pets Welcome
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Route 66 house; Litchfield IL; Pets welcome

Route 66 house; Litchfield IL; Pets welcome

Litchfield
The price is AU$250 per night from 30 Nov to 1 Dec
AU$250
includes taxes & fees
30 Nov - 1 Dec
Located in Litchfield, this vacation home is within a 5-minute drive of Litchfield Museum and Route 66 Welcome Center and Litchfield Carnegie Public ...
Route 66 house; Litchfield IL; Pets welcome
Chestnut House; Litchfield, IL;  Pets Welcome

Chestnut House; Litchfield, IL; Pets Welcome

Litchfield
The price is AU$268 per night from 30 Nov to 1 Dec
AU$268
includes taxes & fees
30 Nov - 1 Dec
With a stay at this vacation home in Litchfield, you'll be within a 5-minute drive of Madison Park and Litchfield Carnegie Public Library.
Chestnut House; Litchfield, IL; Pets Welcome
Harrison House; Litchfield, IL; Pets welcome

Harrison House; Litchfield, IL; Pets welcome

Litchfield
The price is AU$276 per night from 6 Nov to 7 Nov
AU$276
includes taxes & fees
6 Nov - 7 Nov
Located in Litchfield, this vacation home is on a lake, within a 15-minute walk of Litchfield City Hall and Litchfield Carnegie Public Library.
Harrison House; Litchfield, IL; Pets welcome
Victorian Carlinville home on Rt. 66

Victorian Carlinville home on Rt. 66

Carlinville
You'll be centrally located in Carlinville with a stay at this vacation home, and 4 minutes by foot from Carlinville Public Square.
Victorian Carlinville home on Rt. 66
Kirkham Train House; PETS WELCOME

Kirkham Train House; PETS WELCOME

Litchfield
With a stay at this vacation home in Litchfield, you'll be within a 10-minute walk of Litchfield Museum and Route 66 Welcome Center and Litchfield Carnegie Public ...
Kirkham Train House; PETS WELCOME
Plainview Vineyard Retreat Sleeps 8

Plainview Vineyard Retreat Sleeps 8

2 out of 5
Shipman
The price is AU$621 per night from 25 Nov to 26 Nov
AU$621
includes taxes & fees
25 Nov - 26 Nov
With a stay at this vacation home in Shipman, you'll be 30.8 mi (49.5 km) from Mississippi River and 6 mi (9.6 km) from Beaver Dam State Park.
Plainview Vineyard Retreat Sleeps 8
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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.

Gillespie Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Gillespie vacation homes are the perfect way for you to wing it.

Holiday houses in Gillespie let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Gillespie in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Gillespie adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Gillespie with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Gillespie vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Gillespie Holiday Homes essential information

Accommodation
10 Holiday Homes
Lowest Price
AU$126
Highest Price
AU$725
Popular accommodation
Edwards House; Litchfield, IL; Pets welcome, The Carlinville Cottage, Jackson House; Pets Welcome, Route 66 house; Litchfield IL; Pets welcome, Chestnut House; Litchfield, IL; Pets Welcome, Harrison House; Litchfield, IL; Pets welcome, Victorian Carlinville home on Rt. 66 , Kirkham Train House; PETS WELCOME, Plainview Vineyard Retreat Sleeps 8

Top trending hotels in Gillespie

Baymont by Wyndham Litchfield

Baymont by Wyndham Litchfield

2.5 out of 5
1405 W Hudson Dr, Litchfield, IL
Fully refundableReserve now, pay when you stay
The price is AU$152 per night from 6 Nov to 7 Nov
AU$152
includes taxes & fees
6 Nov - 7 Nov
With a stay at Baymont by Wyndham Litchfield in Litchfield, you'll be within a 5-minute drive of Litchfield Museum and Route 66 Welcome Center and Litchfield ...
Baymont by Wyndham Litchfield
Holiday Inn Express & Suites Litchfield West, an IHG Hotel

Holiday Inn Express & Suites Litchfield West, an IHG Hotel

2.5 out of 5
4 Thunderbird Circle, Litchfield, IL
Fully refundable
The price is AU$169 per night from 23 Nov to 24 Nov
AU$169
includes taxes & fees
23 Nov - 24 Nov
Located in Litchfield, Holiday Inn Express & Suites Litchfield West, an IHG Hotel is in the business district, within a 5-minute drive of Litchfield Museum and ...
Holiday Inn Express & Suites Litchfield West, an IHG Hotel
Hampton Inn by Hilton Litchfield

Hampton Inn by Hilton Litchfield

2.5 out of 5
11 Thunderbird Circle, Litchfield, IL
Fully refundableReserve now, pay when you stay
The price is AU$161 per night from 22 Nov to 23 Nov
AU$161
includes taxes & fees
22 Nov - 23 Nov
Located in Litchfield, Hampton Inn by Hilton Litchfield is in the business district, within a 5-minute drive of Litchfield Museum and Route 66 Welcome Center ...
Hampton Inn by Hilton Litchfield
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Super 8 by Wyndham Staunton

Super 8 by Wyndham Staunton

2 out of 5
1527 Herman Rd, Staunton, IL
Fully refundableReserve now, pay when you stay
The price is AU$126 per night from 6 Nov to 7 Nov
AU$126
includes taxes & fees
6 Nov - 7 Nov
Located in Staunton, Super 8 by Wyndham Staunton is within a 5-minute drive of Henry's Rabbit Ranch and Timber Lakes Golf Course.
Super 8 by Wyndham Staunton
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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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^Subject to availability and chosen travel dates.