Highland Holiday Rentals

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Holiday Rentals in Highland

Fridge, microwave, oven, stovetop
Craftsman styled home in the heart of downtown Highland
10.0 out of 10, Exceptional, (31)
"We stayed here as a waypoint to the eclipse. Our party size dwindled from 11 down to 4 so we each had about 3 beds to choose from, and a bathroom each of our own. Highland is a nice little Swiss village and we enjoyed the proximity to the village square."
Craftsman styled home in the heart of downtown Highland
Property grounds
❤️Comfortable Family Home❤️
10.0 out of 10, Exceptional, (1)
"Good location near places, host was super friendly and very accommodating!"
❤️Comfortable Family Home❤️
Property grounds
3 Bedroom Loft overlooking water
9.6 out of 10, Exceptional, (103)
"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
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Exterior
Charming Edwardsville Home: Walk to Downtown!
9.6 out of 10, Exceptional, (4)
"We have stayed at this home before and like it."
Charming Edwardsville Home: Walk to Downtown!
Fridge, microwave, oven, stovetop
Historic Lebanon, quiet 2 Bedroom 2 Bath home!
10.0 out of 10, Exceptional, (22)
"House was in a great location and convenient to local stores. House was clean and had all the amenities we needed for the week. Thank you for sharing your home!"
Historic Lebanon, quiet 2 Bedroom 2 Bath home!
3 bedrooms, iron/ironing board, free WiFi, bed sheets
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
Property grounds
3 Bedroom Home - Lake Views on 3 Sides
9.4 out of 10, Exceptional, (88)
"This property is all about the lake front location. Very relaxing to sit on the deck and watch the geese/ducks/turtles. House is well stocked and is suited for 2 families, with living areas and bathrooms on the main and lower levels. A great location for relaxation."
3 Bedroom Home - Lake Views on 3 Sides
Fridge, microwave, oven, stovetop
Private 4 Bedroom Home with a hot tub
9.6 out of 10, Exceptional, (45)
"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
Property grounds
THE NEST getaways&gatherings, beach/lake sleeps 20+
10.0 out of 10, Exceptional, (30)
"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+
Private kitchen
Cozy Corner Mascoutah
9.4 out of 10, Exceptional, (43)
"Close to restaurants and other facilities."
The price is NZ$318
includes taxes & fees
3 Jun - 4 Jun
Cozy Corner Mascoutah
Exterior
Downtown Midcentury Home- Walk to Everything!
10.0 out of 10, Exceptional, (18)
"House was very open for it being an older style home. Rooms were really good size and it was very clean. Hosts were nice and responded quick when needed!"
Downtown Midcentury Home- Walk to Everything!
Property grounds
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock
10.0 out of 10, Exceptional, (17)
"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
Private kitchen
5 bedrooms near SAFB
9.0 out of 10, Wonderful, (4)
"We loved our stay"
5 bedrooms near SAFB
Private kitchen
Cozy Historic Downtown Edwardsville Charmer
10.0 out of 10, Exceptional, (2)
"Love this older home with a ton of great updates. Super clean with nice touches of nice towels, coffee and creamer, and soap/shampoo and conditioner We loved our stay. There are 2 other apartments in the home so you will hear other people in your stay but it didn’t bother us at all."
Cozy Historic Downtown Edwardsville Charmer
Fridge, microwave, oven, stovetop
Skyline - Military/Family Friendly
9.8 out of 10, Exceptional, (6)
"We rented this place for a long weekend to attend oir nephews high school graduation. Alex amd Sarah Beth were in contact with us from tie tike tue reservation was completed. They were very responsive to any questions we had and made the experience extremely pleasant. The unit is nicely decorated and very comfortable! The skyline artwork is beautiful!"
Skyline - Military/Family Friendly
Fridge, microwave, oven, stovetop
Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly
10.0 out of 10, Exceptional, (28)
"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
Fridge, microwave, oven, stovetop
The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB
The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB
Fridge, microwave, oven, stovetop
The Jetsetter -
10.0 out of 10, Exceptional, (2)
"Great property with all the amenities a person needs for a stay. I enjoyed my stay here."
The Jetsetter -
Exterior
Walking distance to Breese Legion and Main st
10.0 out of 10, Exceptional, (7)
"Jake was a great host with excellent suggestions for places to eat. The response to questions was almost immediate. Breese, Illinois is a great place for a stay. If you have an event in southern Illinois, this is the place to stay!"
Walking distance to Breese Legion and Main st
Fridge, microwave, oven, stovetop
Cali Coast * Small home in quiet neighborhood
9.4 out of 10, Exceptional, (6)
"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
Don't see what you're looking for?
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

In-room safe, desk, iron/ironing board, free WiFi
Seasons Inn & Suites Highland
2.5 star property
8.4 out of 10, Very good, (500)
"Everything was fine"
The price is NZ$181
includes taxes & fees
19 May - 20 May
Seasons Inn & Suites Highland
Fridge, microwave, oven, stovetop
Craftsman styled home in the heart of downtown Highland
10.0 out of 10, Exceptional, (31)
"We stayed here as a waypoint to the eclipse. Our party size dwindled from 11 down to 4 so we each had about 3 beds to choose from, and a bathroom each of our own. Highland is a nice little Swiss village and we enjoyed the proximity to the village square."
Craftsman styled home in the heart of downtown Highland
Property grounds
❤️Comfortable Family Home❤️
10.0 out of 10, Exceptional, (1)
"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