Vacation rentals in Gillespie

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Top-rated vacation rentals in Gillespie

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Top guest favorite

A well-lit outdoor space is presented, featuring a wooden walkway leading to a cozy fire pit surrounded by natural landscaping. Soft string lights create a warm ambiance, enhancing the serene atmosphere of the wooded area, perfect for evening gatherings.

Apartment in Glen Carbon

4.93 out of 5 average rating, 431 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.

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Superhost

The modern home features a spacious wooden deck with steps leading to a well-maintained garden. Large glass doors dominate the front facade, allowing natural light to flood the interior. Lush trees provide a serene backdrop, complementing the inviting outdoor space.

Home in Fairview Heights

4.85 out of 5 average rating, 145 reviews

Wooded Oasis Free Bottle of wine+brkfst+golf

Enjoy serenity and tranquility at our modern home tucked away in a private setting just 5 short minutes from Downtown St. Louis. Complimentary bottled water, continental breakfast (packaged muffins), and a bottle of wine pamper you the moment you arrive. Unwind in our luxurious multifunction shower and memory foam mattress. Test your swing on our scenic mini-golf/driving mat area or relax around the crackling outdoor fire pit. Spa and special occasion add-on packages available. Private parking.

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Guest favorite

The spacious living area features a combination of modern and rustic elements, with three windows allowing natural light to illuminate the space. Plush seating includes two recliners and a small table, complemented by a stylish desk for work. Exposed brick walls add character to the setting.

Apartment in Litchfield

5 out of 5 average rating, 38 reviews

The State Street Loft | Small Town Charm

Welcome to your spacious 1,700 SF home away from home in the heart of Downtown Litchfield! This 2nd floor loft blends modern updates with old-town charm, featuring 3 comfy bedrooms, 1.5 bathrooms, and soaring ceilings that create an airy, open feel. Enjoy a space with plush seating, high-speed internet, and a workspace - perfect for both relaxation and work. Whether you're here for a weekend escape or an extended stay, this downtown loft is the perfect mix of comfort, style, and convenience.

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Top guest favorite

The front of a cozy cottage features a covered porch with two black chairs positioned beside soft green shrubs. A gravel pathway leads to the entrance, while blurred trees and open space create a natural backdrop under a partly cloudy sky.

Home in Edwardsville

4.97 out of 5 average rating, 103 reviews

Cozy Chicken Cottage

Escape to your own peaceful oasis, where comfort meets tranquility, just steps away from a charming, rustic chicken coop. Immerse yourself in the serene sounds of nature on our tiny farm while you enjoy the fresh air. Start your day with a cup of coffee out on the front porch while you overlook our beautiful pond. Perfect for nature lovers, this peaceful hideaway invites you to unwind, recharge and connect with the rhythms of the country. 35 mins to downtown STL. 15 mins to Edwardsville.

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Guest favorite

An open-concept kitchen and dining area features warm wooden cabinets and a round dining table with matching chairs. The space is illuminated by natural light from skylights and windows, with seating arrangements visible in the background. A cozy living area is positioned to the right.

Farm stay in Pocahontas

4.93 out of 5 average rating, 280 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.

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Top guest favorite

A charming bungalow is featured with a welcoming front porch and contrasting dark door. Surrounding greenery adds to the atmosphere. The light blue exterior complements the bright sky, while sunlight bathes the well-maintained lawn.

Bungalow in Carlinville

4.98 out of 5 average rating, 44 reviews

The Carlinville Sunset Bungalow

Escape to this charming 3-bedroom, 2-bathroom retreat nestled in the heart of historic Carlinville, Illinois. This beautifully renovated home, with its classic bungalow architecture and cozy interior, is the perfect base for exploring the town's rich history and stunning natural beauty. Perfect for families, groups of friends, bridal parties, or work trips. Inside, you’ll find a fully equipped kitchen, laundry facilities, and all the amenities you need for a memorable stay.

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Guest favorite

A living area features a stylish gray sofa and a patterned armchair. A modern console table stands against a textured wall, accented by a wavy light installation. A green plant adds a touch of nature to the space, alongside decorative items on the table.

Tiny home in Alton

4.89 out of 5 average rating, 246 reviews

Romantic tiny home w/ hot tub

The ultimate tiny home retreat you’ve been waiting for. This 500 sqft carriage house was built in 1906! Lovingly and meticulously curated for a perfectly romantic stay. You’ll be a short drive from the always fun Fast Eddie’s Bonair or the gorgeous riverside views. Spend the day walking the Great River Road or trying local shops and restaurants. Looking to stay in? Your space has everything you need for a cozy meal in. Put on a record and relax in your private hot tub.

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Top guest favorite

A cozy living area features a plush sofa and a light-colored area rug. A wooden bookshelf filled with framed pictures and decorative items adds warmth. Soft lighting is provided by a table lamp, and a small side table is positioned nearby, creating a welcoming space.

Apartment in Bunker Hill

4.99 out of 5 average rating, 67 reviews

The Loft

Enjoy a peaceful stay in “Our Nest” loft that is nestled in a pretty neighborhood and within walking distance of two restaurants. Within 15 miles, you can experience several small towns and cities which have so many attractions, recreational activities, restaurants, and bars. “Our Nest” loft is 45 minutes from St.Louis and Lambert Airport . We are also 30 minutes to the beautiful Great River Road. You can visit the city and return to the peace and quiet of our small town

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Top guest favorite

A cozy log cabin is set amidst tall trees, featuring a gabled roof and a stone foundation. The front porch is adorned with chairs and a charcoal grill, providing a shaded space. Surrounding greenery creates a tranquil, natural atmosphere.

Cabin in Brighton

4.97 out of 5 average rating, 117 reviews

Log Cabin with Breathtaking View

Relax, kick back and take in the view. Cozy log cabin nestled in the woods with a breathtaking view of a private 2 acre stocked fishing lake. Private master bedroom features queen sized bed, and attached bath. Loft sleeps four with two full beds and an air mattress. Full kitchen with stove, full size fridge, microwave and dishwasher. Living room with sofa and dining room. Charcoal Grill, fire pit, picnic area, and walking trails. Pets are welcome.

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Top guest favorite

A small, modern building is presented with blue siding and a stone foundation. A wooden pathway leads to a white front door, bordered by simple landscaping with gravel. Lush greenery is visible on both sides, enhancing the sense of privacy.

Guesthouse in Carlinville

4.98 out of 5 average rating, 158 reviews

ThE HiDeAwAy

You’ll be surprised by what’s inside! We’ve designed this space to be more than just a place to stay — it’s an experience, because isn’t that what life’s all about? Perfectly located just two blocks from the town square and only steps from the iconic Million Dollar Courthouse, you’ll also be close to great restaurants and shops. Whether you’re visiting for family, business, or a well-deserved getaway, we hope your stay with us creates lasting memories.

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Guest favorite

Home in Mount Olive

4.87 out of 5 average rating, 104 reviews

Lake House off Route 66

Lake House Cabin is the best property in the area and offers a 2 acre lot at the end of a peninsula off Route 66. *Includes private lake access with fishing dock. *House has a fenced in dog area with doggie door. *Swimming, paddle boat and fishing allowed* *Crappie, bass bluegill, blue cat and channel cat. *Smoking allowed outside* *Pets 2 max *Crate pets when left alone. *4 person paddle boat *4 Guests Max including kids. *Wifi *No parties*

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Top guest favorite

A single-story house features a light-colored exterior with a gray roof. Large windows allow natural light to enter. Shadows cast by nearby trees create a peaceful setting, while a gravel driveway leads to an open outdoor space with seating and rustic decor.

Home in Carlinville

4.97 out of 5 average rating, 122 reviews

The Campground House

Escape to a private retreat just an hour from St. Louis! Our charming getaway offers a peaceful, country atmosphere where you can relax and unwind or dive into nature. Need more space or a unique experience? Check out our sister property, Timberline Ridge - Tiny Piney! Perfect for additional accommodations or a unique change of scenery, Tiny Piney offers cozy and rustic charm that complements your stay at The Campground House.

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