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, 33 reviews
"We were in town for a wedding. House was perfect for our family."
Craftsman styled home in the heart of downtown Highland
❤️Comfortable Family Home❤️
10.0 out of 10, Exceptional, 1 review
"Good location near places, host was super friendly and very accommodating!"
❤️Comfortable Family Home❤️
Cozy Corner Mascoutah
9.4 out of 10, Exceptional, 44 reviews
"If you see the photos you can tell exactly what you're going to get here. It's not a 5-star resort, but the owners have clearly poured a ton of time and effort into transforming this little old house in a functional, convenient place to stay that's just filled with character. I appreciated all the amenities, the wifi worked flawlessly, and the house was well-stocked with everything we might have needed. Thank you so much for letting us stay there!"
The price is NZ$316
includes taxes & fees
23 Jun - 24 Jun
Cozy Corner Mascoutah
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3 Bedroom Home - Lake Views on 3 Sides
9.4 out of 10, Exceptional, 89 reviews
"A lot of room in the house for several people. Everything worked as it should. Kids loved the basement, with walkout to pond. Very nice sitting on the deck, so peaceful."
3 Bedroom Home - Lake Views on 3 Sides
Historic Lebanon, quiet 2 Bedroom 2 Bath home!
10.0 out of 10, Exceptional, 25 reviews
"The property was clean and quiet"
Historic Lebanon, quiet 2 Bedroom 2 Bath home!
3 Bedroom Loft overlooking water
9.6 out of 10, Exceptional, 103 reviews
"Our stay at this quaint property was nothing short of perfect. Nestled in a serene and quiet countryside, this charming 3-bedroom bungalow was just what my brother and I needed for our 5-night stay. The home was only a few minutes away from visiting our parents in Collinsville; the purpose of our trip. What truly set it apart was the seamless blend of homely comforts and vacation luxury. Very clean and well-maintained, it felt like our own slice of countryside paradise, where nature and...
3 Bedroom Loft overlooking water
Private 4 Bedroom Home with a hot tub
9.4 out of 10, Exceptional, 46 reviews
"Great house! Close to everything! Comfortable beds, kitchen is awesome, basement has games & pool table. The rooster in the morning reminded me of my great grandmothers house! We will definitely rent this house again. Heidi is very helpful if you have questions!"
Private 4 Bedroom Home with a hot tub
Charming Edwardsville Home: Walk to Downtown!
9.6 out of 10, Exceptional, 5 reviews
"We had guests visiting from Michigan and used The Seedling property as our base of operations. We explored Edwardsville and the surrounding area, much of which was walkable. We loved our time at this property! It was very cute and had plenty of space for two couples and one child."
Charming Edwardsville Home: Walk to Downtown!
Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly
10.0 out of 10, Exceptional, 29 reviews
"It is peaceful and quiet; cozy, and pretty well equipped to handle our cooking needs. The location is perfect for visiting family in the area. We will definitely stay in Everwood Cottage again!"
Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly
THE NEST getaways&gatherings, beach/lake sleeps 20+
10.0 out of 10, Exceptional, 30 reviews
"We enjoyed a boat rental and tubing, roasting marshmallows at night, and hanging out with the family over the Labor Day Weekend."
THE NEST getaways&gatherings, beach/lake sleeps 20+
Downtown Midcentury Home- Walk to Everything!
10.0 out of 10, Exceptional, 19 reviews
"Could not have been more pleased. Quality home, spacious, easy access, and walking to down town area. Owner accommodated our request to come a little early to decorate for a birthday. Great to gather around the big dining table and the outside patio. Not a complaint but it would be great to have a couple extra fold up chairs for outside. That is a lovely area as well. Everyone raved about their bed - comfort. We loved the Nespresso coffee too. And maybe there was a coffee pot but we didn’t see...
Downtown Midcentury Home- Walk to Everything!
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock
10.0 out of 10, Exceptional, 17 reviews
"Our families had so much fun on our stay. Everyone enjoyed the slide and beach. When a brief storm would come through, there was plenty to do inside to keep all entertained! The house was fully stocked. The only thing I would recommend is a bigger toaster. For a house that holds so many, a 2 slice toaster wasn’t the best.(we made BLTs) There is a toaster oven so we figured it out. We did have one issue that arose. I sent the host a message and Coach was there to fix it very quickly. Definitely a...
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock
Reel 'Em Inn
9.6 out of 10, Exceptional, 4 reviews
"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
8.0 out of 10, Very good, 5 reviews
"We loved our stay"
5 bedrooms near SAFB
Cozy Historic Downtown Edwardsville Charmer
10.0 out of 10, Exceptional, 2 reviews
"This was such a nice home, perfect for my family's stay in the area. We appreciated having access to the full kitchen, dining room and living room to make our stay comfortable."
Cozy Historic Downtown Edwardsville Charmer
Skyline - Military/Family Friendly
9.8 out of 10, Exceptional, 8 reviews
"Great location, anything you need is minutes away. The host provided almost any necessity you would need if you were at home and was very friendly and receptive when I had any questions. I would definitely stay here again."
Skyline - Military/Family Friendly
The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB
The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB
The Jetsetter -
10.0 out of 10, Exceptional, 2 reviews
"Great property with all the amenities a person needs for a stay. I enjoyed my stay here."
The Jetsetter -
Walking distance to Breese Legion and Main st
10.0 out of 10, Exceptional, 8 reviews
"A++"
Walking distance to Breese Legion and Main st
Cali Coast * Small home in quiet neighborhood
9.4 out of 10, Exceptional, 6 reviews
"Smooth in every aspect,super quiet and comfortable small accom,great response from owner,def stay again when I visit as in a good location"
Cali Coast * Small home in quiet neighborhood
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See all available properties in Highland
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.

Other types of properties in Highland you may be interested in

Seasons Inn & Suites Highland
2.5 star property
8.4 out of 10, Very good, 508 reviews
"Breakfasts were goid. Room.was quiet. Housekeeping didnt bother us. "
The price is NZ$191
includes taxes & fees
23 Jun - 24 Jun
Seasons Inn & Suites Highland
Craftsman styled home in the heart of downtown Highland
10.0 out of 10, Exceptional, 33 reviews
"We were in town for a wedding. House was perfect for our family."
Craftsman styled home in the heart of downtown Highland
❤️Comfortable Family Home❤️
10.0 out of 10, Exceptional, 1 review
"Good location near places, host was super friendly and very accommodating!"
❤️Comfortable Family Home❤️
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Highland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Highland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Highland. Seeing all the best attractions is bound to make you fall in love with Highland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Highland short-term rentals, that won’t be hard to do.

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.

Recent reviews of Highland properties
Expedia verified reviews