Vacation rentals in Gillespie

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Top-rated vacation rentals in Gillespie

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Apartment in Edwardsville

4.91 out of 5 average rating, 223 reviews

Edwardsville Apartment - The Woodland Suite

The apartment in the lower level of the home has recently been renovated, with a walk-out private entrance, a full kitchen & dining area, full bath, bedroom and a cozy living space. Situated just 35 minutes from downtown St Louis, in the safe and affluent community of Edwardsville, this property sits in a quiet cul de sac on a wooded lot right in the heart of the city. We are just a few minutes from the SIUE campus, Edwardsville HS, & I-270. Coffee/restaurants/shops/parks/trails just 2 min away.

Jul 9 – 16

R2,788 ZAR per night
Guest favorite

Farm stay in Pocahontas

4.95 out of 5 average rating, 154 reviews

Hilltop Ranch Home on 25 acres bathed in starlight

Welcome to our Hilltop Ranch Home! You will find a relaxing getaway for your entire family or several couples. There is 1800 sq ft on the first floor including a master bedroom with ensuite bathroom boasting a jacuzzi tub, a fully stocked kitchen, gas fireplace, and an attached 2-car garage. In the walkout basement, there is a fourth bedroom, full bath and a TV area. A patio adjoining the dining room, a charcoal grill, and full-size hot tub-all perfect for entertaining your whole group.

Nov 26 – Dec 3

R3,411 ZAR per night
Guest favorite

Home in Brownstown

4.93 out of 5 average rating, 146 reviews

House By The Woods 2-bedroom house with fireplace

House with propane fireplace, 1 bathroom, 2 bedrooms, & futon in living room that can sleep up to 6 total. It is surrounded by woods that has a side outdoor porch with a seating area & table with chairs to eat/drink your favorite drink/coffee anytime of the day or night. Firepit area for roasting hotdogs or marshmallows. Firewood & picnic table on premises. Propane grill near back patio. Small kids play area in front where parents can still sit relaxing on side patio and watch the kids.

Oct 12 – 19

R2,499 ZAR per night

Popular amenities for Gillespie vacation rentals

Other great vacation rentals in Gillespie

Guest favorite

Home in Gillespie

4.93 out of 5 average rating, 60 reviews

Our Little House

Dec 8 – 15

R1,931 ZAR per night
Guest favorite

Home in Carlinville

4.97 out of 5 average rating, 95 reviews

The Campground House

Feb 16 – 23

R3,441 ZAR per night
Guest favorite

Home in Carlinville

5.0 out of 5 average rating, 11 reviews

Historic Home near Blackburn & Square 2 King beds

Apr 22 – 29

R2,535 ZAR per night
Guest favorite

Home in Medora

4.8 out of 5 average rating, 10 reviews

country living

Nov 5 – 12

R2,065 ZAR per night
Superhost

Cottage in Staunton

5.0 out of 5 average rating, 13 reviews

Luxury Lakeview Bungalow #14 near St. Louis

Jun 4 – 11

R2,793 ZAR per night
Guest favorite

Home in Carlinville

5.0 out of 5 average rating, 44 reviews

Victorian Home on Rt. 66

Jul 10 – 17

R4,677 ZAR per night
Guest favorite

Home in Greenville

4.9 out of 5 average rating, 72 reviews

Cozy Home on College Ave

Jun 7 – 14

R1,633 ZAR per night
Guest favorite

Home in Troy

4.98 out of 5 average rating, 44 reviews

No Frills Home on 2 Acres to yourself!

May 21 – 28

R1,665 ZAR per night
Guest favorite

Loft in Hillsboro

4.9 out of 5 average rating, 49 reviews

Downtown Hillsboro Loft

May 8 – 15

R1,952 ZAR per night
Guest favorite

Guesthouse in Jerseyville

4.99 out of 5 average rating, 77 reviews

Cozy cabin on farm near Jerseyville and Grafton IL

Sep 18 – 25

R2,575 ZAR per night
Guest favorite

Home in Hillsboro

4.91 out of 5 average rating, 46 reviews

2bedroom HOUSE close to downtown!

Oct 19 – 26

R1,217 ZAR per night
Superhost

Barn in Alhambra

4.84 out of 5 average rating, 58 reviews

Boho Barn Loft Countryside Getaway

Jun 20 – 25

R3,254 ZAR per night

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