Holiday houses in Highland

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Top-rated holiday rentals in Highland

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Top Guest favourite

Apartment in Edwardsville

4.92 out of 5 average rating, 349 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.

Top Guest favourite

Cabin in Pocahontas

5 out of 5 average rating, 30 reviews

Peaceful | Private | Lakeview | Highland-Breese

Take it easy at this unique and tranquil getaway. This cozy one-bedroom loft/cabin, with a balcony, has a stunning view of a private lake in a serene, country setting. The spacious living room offers added ambiance with a potbelly stove, a pull-out sofa bed, dining table and kitchenette with a Keurig coffee maker, microwave, & refrigerator. Extra amenities include Apple TV, heated towel rack, washer-dryer, electric skillet and portable grill. Covered parking with a private entrance is a bonus.

Guest favourite

Apartment in Saint Jacob

4.92 out of 5 average rating, 25 reviews

A Sweet Spot, catering to Traveling Tech/workers

One bedroom, full bath & kitchen, living room, washer & dryer, closet, Queen bed & deck overlooking lake. 2nd floor apartment over a garage/workshop. One flight of outdoor stairs to enter. Train track about 2 blocks away (maybe 3 trains a day). Approx 30 miles from the Arch & Downtown St. Louis; 25 miles from SIUE; one block from Metro bus stop, Dollar General & Quick Stop; 5 miles from St. Joseph Hospital, and Walmart; 15 miles to Anderson Hospital and 5 miles to I-70. Bank/ATM nearby.

Guest favourite

Farm stay in Pocahontas

4.93 out of 5 average rating, 236 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.

Top Guest favourite

Apartment in Edwardsville

4.98 out of 5 average rating, 120 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.

Top Guest favourite

Home in Highland

5 out of 5 average rating, 87 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.

Guest favourite

Guesthouse in Mascoutah

4.95 out of 5 average rating, 248 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.

Top Guest favourite

Loft in Vandalia

4.95 out of 5 average rating, 280 reviews

Modern Loft in Historic Downtown

Lincoln’s Loft is close to everything making it easy to plan your visit to downtown Vandalia. This loft offers a bedroom, full kitchen and bath, dining room, living room with a pull out sofa, and large smart TV. This loft also offers beautiful views of the oldest State Capitol in IL and is within walking distance to many restaurants, bars, and local shops. It is located on the 3rd level and will require you to climb 2 flight of stairs. For events please contact the host!

Top Guest favourite

Loft in Highland

5 out of 5 average rating, 21 reviews

Loft on the Square

NEWLY RENOVATED 150-year-old building on Highland, Illinois iconic town square. This charming space offers a small-town charm but just a short 45-minute drive to St. Louis. Come and relax in this one-of-a-kind space that is walking distance to many local restaurants, shops, and bars. Make new memories with family and friends (PET FRIENDLY!) in this beautiful space. This space is not handicap accessible as there are steep steps to the second story of this building.

Top Guest favourite

Home in Mascoutah

4.96 out of 5 average rating, 450 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.

Top Guest favourite

Home in Greenville

4.95 out of 5 average rating, 168 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!

Guest favourite

Home in Edwardsville

4.91 out of 5 average rating, 149 reviews

Brick B&B - 3Bed 2Full Bath! Downtown Edwardsville

Welcome to the Brick B&B! Proudly located in Downtown Edwardsville, IL. This newly renovated house is located in a quite neighborhood, only 28 min drive from Downtown St. Louis. Enjoy a short walk or a quick drive to many local coffee shops, boutiques, spas, restaurants, and bars. Other local activities include: City Park only a 3 min walk, an entrance to the Madison County Transit bike path is a quick 6 min walk, & 10 min drive to SIUe campus. Permit # 031602