Highland Holiday Rentals

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Holiday Rentals in Highland

Craftsman styled home in the heart of downtown Highland
10.0 out of 10, Exceptional, (64)
"Couldn't ask for a better place to stay in town for our son's wedding nearby at Schwartz Barn. Had plenty of space, bedrooms and common areas to come together to share a meal or just catch up and visit with family while also finding quiet spots to catch up on rest as needed. Can't express our gratitude enough!"
Craftsman styled home in the heart of downtown Highland
The Swiss Post Apartment B
2.0 star property
10.0 out of 10, Exceptional, (2)
"Very nice apartment in a great location! Really enjoyed our stay!"
The Swiss Post Apartment B
The Loft on the Square
10.0 out of 10, Exceptional, (2)
"Family stay over holidays. Place was decorated and made us feel at home. Love the historical touches, would stay here again. "
The Loft on the Square
The Swiss Post Apartment A
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautifully decorated, clean, and perfect location for my work trip to Highland. Safe neighborhood, food very close, farmers market in the square. Easy check in and out. Second story location with staircase to enter."
The Swiss Post Apartment A
3 Bedroom Loft overlooking water
9.6 out of 10, Exceptional, (111)
"Beautiful property overlooking the lake, great communication, and kind host. "
3 Bedroom Loft overlooking water
Cozy Corner Mascoutah
9.6 out of 10, Exceptional, (69)
"Perfect rental property. My family and I enjoyed our stay in the Cozy Corner. Great location."
The price is AU$304
includes taxes & fees
4 Nov - 5 Nov
Cozy Corner Mascoutah
3 Bedroom Home - Lake Views on 3 Sides
9.6 out of 10, Exceptional, (95)
"This place is perfect for your family and works out super for staying in the area for work. Would recommend! "
3 Bedroom Home - Lake Views on 3 Sides
THE NEST getaways&gatherings, beach/lake sleeps 20+
10.0 out of 10, Exceptional, (38)
"The house was wonderful and the beach a lot of fun. It was the perfect family vacation spot!"
THE NEST getaways&gatherings, beach/lake sleeps 20+
Charming 2-bedroom, two bathroom house in Carlyle, pets welcome!
The price is AU$489
includes taxes & fees
20 Oct - 21 Oct
Charming 2-bedroom, two bathroom house in Carlyle, pets welcome!
The Maple Cottage
10.0 out of 10, Exceptional, (2)
"Amazing place to stay! Very clean and nice inside. Everything you needed was provided, a yard and carport as well! The owners are super friendly and sweet. Everything you need is 5 minutes down the road. The house was extremely pretty and roomy! Our family loved staying here and would absolutely do it again next time! Thank you for everything!!"
The Maple Cottage
Skyline - Military/Family Friendly
10.0 out of 10, Exceptional, (16)
"The location was perfect! Alex was a great host and responded immediately when we had any questions. Would recommend. "
Skyline - Military/Family Friendly
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock
10.0 out of 10, Exceptional, (19)
"Plenty of private space, gathering space, eating area and food prep supplies. Lots to do as well. There was even a rainbow over the lake the last day."
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock
Historic 4-bedroom house in Glen Carbon with AC
2.0 star property
10.0 out of 10, Exceptional, (1)
"Room was clean and very affordable for 5 people"
Historic 4-bedroom house in Glen Carbon with AC
Reel 'Em Inn
9.2 out of 10, Wonderful, (5)
"The overll booking porcess. Bokked through Expedia and then they wnet trough VRBO. Did not like the overall way it was handled. Property itself suited outr purpose."
Reel 'Em Inn
Private 4 Bedroom Home with a hot tub
9.4 out of 10, Exceptional, (51)
"Great space for big family or 2. Communication with owner was quick and easy. Quick to resolve questions. We really enjoyed our stay. thanks"
Private 4 Bedroom Home with a hot tub
The Beaumont Retreat
10.0 out of 10, Exceptional, (3)
"Place was great! "
The Beaumont Retreat
Cozy Historic Downtown Edwardsville Charmer
9.4 out of 10, Exceptional, (13)
"Wonderful location for what we needed! Comfortable beds and great amenities. Lots of little touches and extras."
Cozy Historic Downtown Edwardsville Charmer
Charming 1BR Near Historic Downtown Edwardsville & SIUE
Charming 1BR Near Historic Downtown Edwardsville & SIUE
The Hangar - Healthcare/Military friendly!
10.0 out of 10, Exceptional, (17)
"We had a great time. Room was clean and spacious. Very secure location."
The Hangar - Healthcare/Military friendly!
Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly
10.0 out of 10, Exceptional, (35)
"The cottage is a very nice and quiet place to stay for our short vacation. It had everything we wanted and the washer and dryer came in handy. It was a perfect place to bring our dog with for his first trip. "
Everwood Cottage ^ Trees, Birds, and Quiet! Military 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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Top Highland Hotel Reviews

Find out more about Highland

Everything you need to know about Highland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Highland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland holiday rentals we have selected for you start as low as AU$304 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Highland rentals

At Expedia, we put the best Highland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Highland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

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.