Holiday houses in Highland

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Highland

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

1 of 1 pages1 / 1

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, 436 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.

FamilyLocationCheckout

Guest favourite

A spacious living area features a comfortable seating arrangement with a brown sofa and a bright yellow chair. A round coffee table is centered on a patterned area rug, with natural light filtering through large windows dressed in light curtains. A flat-screen TV is mounted on the wall.

Home in Caseyville

4.87 out of 5 average rating, 124 reviews

The Maple Cottage

Enjoy a stylish Two bedroom cottage Nestled in the backroads of Caseyville, our charming house offers the perfect blend of comfort and convenience. The Maple Cottage is just a stone's throw away from I64 and a vibrant shopping district in Fairview Heights, making it easy to explore local boutiques, restaurants, and entertainment options. The cottage features a comfortable living area, a fully equipped kitchen for your culinary adventures, and a peaceful bedrooms designed for restful nights.

FamilyValueParking

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, 112 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.

LocationValueAccuracy

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, 105 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.

FamilyLocationAccuracy

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, 282 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.

FamilyValueParks

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, 163 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.

FamilyLocationQuiet

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

5.0 out of 5 average rating, 118 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.

LocationValueBathroom

Top Guest favourite

An outdoor dining area is presented under a wooden pergola, featuring a table and chairs surrounded by lush greenery. The modern home is visible in the background, with large windows allowing for natural light. A flower pot adds a touch of color to the space.

Cottage in Pocahontas

5.0 out of 5 average rating, 46 reviews

Cozy Cottage on 6 Private Acres!

• 2 bedrooms, sleeps 4 • 1 x king size bed and 2 x single beds. • 1 full bathroom, walk in shower. • Full kitchen, large island, all essentials. • Extra bed linens, blankets and pillows. • Hangers, iron & clothes storage. • Body soap, conditioner, shampoo, hair dryer. • Softened and filtered water • Central HVAC • WI-FI & ROKU TV • 2 car garage with level 2 EV charging station. • Outdoor dining with pellet grill • Plenty of parking space • Self check-in • No stairs!

FamilyLocationKitchen

Top 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, 245 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!

ValueLocationBathroom

Top Guest favourite

Home in Lebanon

5.0 out of 5 average rating, 552 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.

LocationValueSleep quality

Guest favourite

An aerial view captures the Burnside Bay House nestled on a spacious property surrounded by lush greenery. The landscape features winding waterways and wooded areas, highlighting the natural beauty and openness of the 27 acres available for exploration.

Home in Carlyle

4.9 out of 5 average rating, 115 reviews

Carlyle Lakehouse on 27+ Acres - Family Friendly!

Welcome to Burnside Bay House, a 4300+ sq. ft home with a huge deck, patio, 2 kitchens, and 27 acres to explore! It's only an hour and 15 minutes from STL! You can walk down to the water or take a short ride to the boat ramp. Bring your boat, jet skis, and water toys. There's plenty of parking on site! Newly remodeled and decorated with carefully selected furnishings & decor. Come relax and enjoy the lake & the views!

ValueLocationAccuracy

Guest favourite

Home in Highland

5.0 out of 5 average rating, 11 reviews

Spacious luxury loft in the heart of Highland!

Stay in the heart of downtown Highland in this spacious luxury loft! You’ll have two cozy bedrooms, a fully equipped gourmet kitchen, and a bright great room with a gas fireplace. Enjoy stunning views of the square and fountain or relax on your large private deck — perfect for morning coffee or evening wine. (Not handicap accessible.)

FamilyLocationCondition