Holiday houses in Highland

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Top-rated holiday rentals in Highland

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

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Top Guest favourite

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, 430 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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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, 144 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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Top Guest favourite

The exterior of a charming bungalow is illuminated at night, showcasing a welcoming front porch with rocking chairs. A large, circular wreath adorns the bright red front door. Nearby, an American flag gently waves, set against a backdrop of landscaped greenery.

Home in Edwardsville

4.99 out of 5 average rating, 110 reviews

Historic Leclaire Cottage on the Park

Be part of the Leclaire National Historic District by calling this timeless, updated 1927 bungalow home for two nights, two weeks or longer! This is a quiet neighborhood full of friends who stop to chat in the twilight. Set your phone down, relax on the porch and let Leclaire take you to a simpler time. Inside, find two separate living rooms w/smart TVs. 2 Qn BDRMS downstairs, 2 twin beds upstairs. Full kitchen&bath stocked with essentials. Complimentary EV charging at N.O. Nelson campus.

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Top Guest favourite

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 favourite

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 favourite

A welcoming front porch features a sturdy wooden door with decorative glass panes. Two wicker chairs with plush cushions are positioned beside a small table, creating a cozy seating area. Natural light highlights the brick exterior and surrounding greenery.

Apartment in Edwardsville

4.97 out of 5 average rating, 160 reviews

Cozy Historic Downtown Edwardsville Charmer

Spacious and cozy with hardwood floors throughout. Beautifully restored to its original 1920’s glory. Set up to meet your needs. Clean, uncluttered spaces, full kitchen, Wi-Fi, and the basics for an easy stay. Third bedroom offers office space in addition to bunk beds. Relax on the front porch in this lovely neighborhood. Just a few blocks from main street’s offering of coffee shops, restaurants & entertainment. MCT bus stop across the street for easy access to SIUE & St. Louis.

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Top Guest favourite

A cozy living area is presented with a daybed adorned with a mix of cushions, accompanied by a small side table. A textured ottoman sits at the center, topped with a decorative tray. Repeating black-and-white checkered patterns are featured on the area rug.

Home in Highland

5 out of 5 average rating, 116 reviews

Beautiful craftsman style home, built in 1930.

Take the stress out of travel knowing you have a home away from home awaiting you. It’s said that wherever you go becomes a part of you somehow. The Nook is a place where friends and family gather and memories are made – the ones you take with you and cherish. It's a place where time stands still allowing you to soak in every moment. The calm pace of this quaint little town and the comfort of the Nook will allow you to pause for a moment, enjoy life, and find your happiness.

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Top Guest favourite

The exterior of the carriage house is displayed, featuring a charming entrance with a white front door and large windows. A wooden bench provides seating on the porch, and the garage door is painted in a contrasting color. Surrounding greenery enhances the inviting appearance.

Guesthouse in Mascoutah

4.97 out of 5 average rating, 319 reviews

The Carriage House

Cute and cozy, this tiny carriage house is packed with charm. Originally used as a place to store a horse-drawn carriage, this delightful building has been completely refurbished with everything you need for a clean and comfortable stay, including endless hot water, vinyl plank flooring, front porch, laundry, and eat-in kitchen. The bedroom has a queen bed, comfy recliner, and Roku-enabled TV. Please notify me if you are bringing any pets. I want to know dog breed and age.

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Top Guest favourite

The charming Victorian house features a distinct architectural style with decorative trim and a welcoming front porch. A small yard is visible, along with a neighboring shed, and a gravel path leads to the porch steps, surrounded by lush greenery.

Home in Mascoutah

4.96 out of 5 average rating, 491 reviews

The Doll House

Not suitable for work groups. Our Victorian doll house is Listed on the National Register of Historic Places, it maintains its original features yet is updated with modern conveniences. The kitchen is fully equipped. Wifi is available and the home is within walking distance of restaurants and shopping. Enjoy the peaceful backyard while you sit on the porch & relax. An easy drive 4 miles south of I-64. No third party bookings. Use of property to registered guests only.

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Guest favourite

A welcoming living area features a light gray sofa with decorative pillows and a square glass coffee table. A modern accent chair is positioned beside the table, and a shelf displays simple décor. Natural light enters through a large window, creating a bright atmosphere.

Home in Greenville

4.96 out of 5 average rating, 241 reviews

Cozy Home on College Ave

Welcome to our adorable two-bedroom home in the heart of Greenville! Nestled less than half a mile from Greenville University, this cozy retreat offers easy access to 1-70 and Greenville Square. Skip the traditional hotel and enjoy the comfort of a simple home at an affordable rate. With St. Louis just under an hour away, you'll experience the perfect blend of charm, convenience, and proximity to local attractions. Book now for a delightful stay in this inviting space!

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Top Guest favourite

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, 116 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 favourite

Home in Lebanon

5 out of 5 average rating, 549 reviews

Close to St Louis, Scott AFB & McKendree

"Bungalow Five-O-Two" is located in historic Lebanon, Illinois. Built in 1885, Bungalow-Five-Two has been completely renovated to offer modern accommodations while maintaining its charm and integrity. Conveniently located within walking distance to McKendree University and the amazing restaurants and quaint shops of Lebanon. Only a 15 minute drive to Scott AFB, 10 minutes to MIdAmerica Airport, and 30 minutes to St. Louis.

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