Holiday rentals in Gillespie

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Gillespie

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

Guest favourite

Flat 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.

9–16 Jul

₹12,255 per night
Guest favourite

Home in St. Peters

4.88 out of 5 average rating, 306 reviews

Private Walkout w King Bed & Bath + large livingrm

Our house sits in a very quiet and safe neighborhood. When you stay with us you will enter through the walkout basement. You have full access to our very private downstairs apartment. This will enter you right into the very large living area. The master bedroom is complete with a King bed, black out curtains and walk-in closet. Attached is a full size bathroom with walk-in shower. Amenities include television, DVD, WiFi, Kuerig, mini-fridge and access to patio/porch with backyard fire pit.

22–29 Sep

₹6,231 per night
Guest favourite

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.

25 Aug – 1 Sep

₹14,995 per night

Popular amenities for Gillespie holiday rentals

Other great holiday rentals in Gillespie

Guest favourite

Cabin in Carrollton

4.92 out of 5 average rating, 119 reviews

Graham Farm Cabin

1–8 Sep

₹11,641 per night
Guest favourite

Home in Gillespie

4.93 out of 5 average rating, 60 reviews

Our Little House

26 Oct – 2 Nov

₹8,486 per night
Guest favourite

Home in Carlinville

4.97 out of 5 average rating, 95 reviews

The Campground House

16–23 Feb

₹15,123 per night
Guest favourite

Home in Carlinville

5.0 out of 5 average rating, 11 reviews

Historic Home near Blackburn & Square 2 King beds

3–10 Sep

₹11,142 per night
Guest favourite

Home in Medora

4.8 out of 5 average rating, 10 reviews

country living

5–12 Nov

₹9,078 per night
Superhost

Cottage in Staunton

5.0 out of 5 average rating, 13 reviews

Luxury Lakeview Bungalow #14 near St. Louis

15–22 Apr

₹12,277 per night
Guest favourite

Home in Carlinville

5.0 out of 5 average rating, 44 reviews

Victorian Home on Rt. 66

1–8 Dec

₹21,908 per night
Guest favourite

Home in Greenville

4.9 out of 5 average rating, 71 reviews

Cozy Home on College Ave

23–30 Nov

₹7,177 per night
Guest favourite

Home in Troy

4.98 out of 5 average rating, 44 reviews

No Frills Home on 2 Acres to yourself!

21–28 May

₹8,132 per night
Guest favourite

Home in Hillsboro

4.91 out of 5 average rating, 46 reviews

2bedroom HOUSE close to downtown!

3–10 Jan

₹5,394 per night
Guest favourite

Guest house in Jerseyville

4.99 out of 5 average rating, 77 reviews

Cozy cabin on farm near Jerseyville and Grafton IL

11–18 Feb

₹11,319 per night
Guest favourite

Loft in Hillsboro

4.9 out of 5 average rating, 49 reviews

Downtown Hillsboro Loft

8–15 Sep

₹8,582 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Macoupin County
  5. Gillespie