Highland Holiday Rentals

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Holiday Rentals in Highland

The Swiss Post Apartment A

2.0 star property
The Swiss Post Apartment A

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (44)
"This is gem! Lots of room for multiple families and people. We were there for a wedding and it was the perfect spot for everyone to get ready. Bathrooms are great size and the extra amenities thru out the home are great. (Coffee, soap, shampoo, lotion, etc). Back porch and parking was perfect for all the guests. Highly recommend and will be back! "
Craftsman styled home in the heart of downtown Highland

The Loft on the Square

The Loft on the Square

The Swiss Post Apartment B

2.0 star property
The Swiss Post Apartment B

3 Bedroom Loft overlooking water

9.6 out of 10, Exceptional, (105)
"15 minutes from gateway center in Collinsville, IL. Very nice neighborhood with a beautiful lake that is filled with fish, turtles, and ducks that our kids loved. We enjoyed the comfortable beds."
3 Bedroom Loft overlooking water

Private 4 Bedroom Home with a hot tub

9.4 out of 10, Exceptional, (50)
"Great house. Unique location in the country. Great access to St Louis and horse track in Collinsville, Illinois."
Private 4 Bedroom Home with a hot tub

Historic Lebanon, quiet 2 Bedroom 2 Bath home!

10.0 out of 10, Exceptional, (34)
"The property was inviting and had everything we needed for a comfortable stay. The neighborhood was quiet and we felt safe. We plan to stay here again when we visit family in the area. "
Historic Lebanon, quiet 2 Bedroom 2 Bath home!

Charming Edwardsville Home: Walk to Downtown!

9.8 out of 10, Exceptional, (9)
"We really enjoyed our stay at the Seedling. It is impeccably clean and in a great location. It is within walking distance of downtown and very close to the major shopping and entertainment of Edwardsville. The communications from the property manager are awesome. We loved the decorations and the peacefulness of the area."
Charming Edwardsville Home: Walk to Downtown!

3 Bedroom Home - Lake Views on 3 Sides

9.4 out of 10, Exceptional, (91)
"The pictures match the property very well. House was clean stocked with everything that you would need for a family. There was good fishing on the lake."
3 Bedroom Home - Lake Views on 3 Sides

Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly

10.0 out of 10, Exceptional, (33)
"Great place to stay near McKendree Univ. Kitchen was better equipped than some house VRBO’a we have stayed in. Beautifully decorated and exactly as the pictures show. We will be back! Thank you for sharing your cottage with us. "
Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly

The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB

10.0 out of 10, Exceptional, (2)
"Everything was as described in the listing. No issues during my stay! "
The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB

The Hangar - Healthcare/Military friendly!

10.0 out of 10, Exceptional, (13)
"This place was awesome, very clean and had everything we needed, would definitely consider staying again!"
The Hangar - Healthcare/Military friendly!

THE NEST getaways&gatherings, beach/lake sleeps 20+

10.0 out of 10, Exceptional, (36)
"This is our second stay at the Nest. We love everything about it. House, Beach, Shade, Outdoor Play Area. The property managers are easy to reach and responsive. Highly recommend a stay here. "
THE NEST getaways&gatherings, beach/lake sleeps 20+

Cozy Corner Mascoutah

9.6 out of 10, Exceptional, (54)
"Perfect night for a quick in and out of town stay. There is a little bar within walking distance that my husband and son went to for a quick beer before bed. Hotels can be hard for a dog so this was exactly what we needed to keep our girl happy. "
The price is AU$300
includes taxes & fees
30 Nov - 1 Dec
Cozy Corner Mascoutah

Downtown Midcentury Home- Walk to Everything!

10.0 out of 10, Exceptional, (21)
"Nice set up and spacious "
Downtown Midcentury Home- Walk to Everything!

The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock

10.0 out of 10, Exceptional, (19)
"We rented the Nest too. We had 8 people there and 11 at the Aerie. Each couple was able to have their own space this way. Adults didn't have to give up their privacy. At the Aerie, the living space, kitchen and rec room were spacious. We were fortunate to have perfect weather so we were outside all day and into the night. The outdoor space was fabulous for outdoor eating and "playing". We all give this venue A thumbs up!"
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock

Reel 'Em Inn

9.6 out of 10, Exceptional, (4)
"The game room was the highlight of the house. Lots of room for the whole group and the bedrooms were very spacious! We really enjoyed our stay and we’re impressed with how nice the house was! Would definitely recommend to stay here!"
Reel 'Em Inn

5 bedrooms near SAFB

7.0 out of 10, Good, (8)
"We loved our stay"
5 bedrooms near SAFB

Cozy Historic Downtown Edwardsville Charmer

10.0 out of 10, Exceptional, (3)
"Nice, comfortable, very clean home. Kurt was very responsive to our questions. Easy to get checked in. Nice to have quite a few basic supplies in the kitchen. Home is within a short walk to downtown Edwardsville. and restaurants close by."
Cozy Historic Downtown Edwardsville Charmer

Skyline - Military/Family Friendly

10.0 out of 10, Exceptional, (12)
"We had the greatest time! Never been to that area and we loved it! Your property was perfect in a perfect location!! We loved it! tMcKendree,Shiloh"
Skyline - Military/Family Friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Highland you may be interested in

Seasons Inn & Suites Highland

2.5 star property
8.2 out of 10, Very good, (534)
"Easy check in. We were on the 3rd floor with King bed. Clean rooms and quite surroundings for a restful sleep."
The price is AU$161
includes taxes & fees
1 Dec - 2 Dec
Seasons Inn & Suites Highland

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (44)
"This is gem! Lots of room for multiple families and people. We were there for a wedding and it was the perfect spot for everyone to get ready. Bathrooms are great size and the extra amenities thru out the home are great. (Coffee, soap, shampoo, lotion, etc). Back porch and parking was perfect for all the guests. Highly recommend and will be back! "
Craftsman styled home in the heart of downtown Highland

The Tibbetts House

3.0 star property
9.0 out of 10, Wonderful, (6)
"Owners were friendly, personable and helpful. We really enjoyed our stay"
The Tibbetts House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Highland?

Yes, there are holiday rentals close to the most popular sights in Highland, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Highland has a good selection of restaurants. Make sure you have time to check out the architecture and lake views during your trip.

What are some of the best holiday rentals that Highland has to offer?

Craftsman styled home in the heart of downtown Highland: This highly rated holiday home rental in Highland is located in the city centre, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Highland?

Expedia has 3 holiday rentals for your stay in Highland.

What can I see and do in Highland?

While you're exploring the area, Silver Lake Park and O'Fallon Family Sports Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Korte Recreation Center and Copper Dock Winery.

What are holiday rentals like in Highland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for small groups.