Holiday Rentals in Highland

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Holiday Rentals in Highland

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
❤️Comfortable Family Home❤️
10.0 out of 10, Exceptional, (1)
"Good location near places, host was super friendly and very accommodating!"
❤️Comfortable Family Home❤️
Historic Lebanon, quiet 2 Bedroom 2 Bath home!
10.0 out of 10, Exceptional, (21)
"Very impressive property within walking distance to McKendree. If we go back for another visit or my child attends there we will definitely rebook"
Historic Lebanon, quiet 2 Bedroom 2 Bath home!
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Charming Edwardsville Home: Walk to Downtown!
10.0 out of 10, Exceptional, (1)
"Everything about my stay was perfect. The home was very well decorated and welcoming. The hosts were great at clearly sharing details about the home before my stay. Upon my arrival, I found that the host had prepared excelent information about the home and surrounding community. The neighborhood is excellent, with a short walk to the downtown area, where you can find many great places to eat and shop. Would definitely recommend this property and will likely plan to stay here again, next time I...
Charming Edwardsville Home: Walk to Downtown!
Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly
10.0 out of 10, Exceptional, (26)
"This place is adorable!! Very peaceful, I loved the big window looking out over the back yard! Plenty of space, but it was just me visiting."
Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly
Cozy Historic Downtown Edwardsville Charmer
10.0 out of 10, Exceptional, (1)
"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
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+
Downtown Midcentury Home- Walk to Everything!
10.0 out of 10, Exceptional, (17)
"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!
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
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 -
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
The Hangar - Healthcare/Military friendly!
10.0 out of 10, Exceptional, (10)
"Close to family and Scott AFB"
The Hangar - Healthcare/Military friendly!
❤️Spacious and Comfortable Family Home❤️
10.0 out of 10, Exceptional, (1)
"We were celebrating one of my friend’s graduation and getting her RN. It was a clean, safe house to meet and stay in. It was easy to go back and forth to the club from there."
❤️Spacious and Comfortable Family Home❤️
General Green is a travelers dream!
10.0 out of 10, Exceptional, (1)
"Everything about this rental was perfect from the initial booking, to communication, to the wonderful little extra touches around the house. It was perfect for my family of 5 to enjoy our trip to IL together. I would absolutely return to this house if I am back in that area again. I have stayed in many VRBOs but this was one of the most pleasant overall experiences that I have had. Thanks so much!"
General Green is a travelers dream!
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
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
Cozy Corner Mascoutah
9.4 out of 10, Exceptional, (42)
"Close to restaurants and other facilities."
The price is €184
per night
4 May - 5 May
Cozy Corner Mascoutah
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
5 bedrooms near SAFB
9.0 out of 10, Wonderful, (4)
"We loved our stay"
5 bedrooms near SAFB
Fully Funished Condo convenient to St Louis and Scott AFB.
9.0 out of 10, Wonderful, (2)
"We had a great stay at Joel's place for a long weekend in Saint Louis. The neighborhood is peaceful and felt very safe. The condo is one of 4 in the building, but we never even heard the neighbors. It's a short drive to numerous restaurant and grocery store options and just 15 minutes to cross over into St. Louis. We enjoyed the beautiful pool on property while we were there. The condo was very clean and well-appointed. While some hosts provide just the minimum to accommodate guests, Joel and...
Fully Funished Condo convenient to St Louis and Scott AFB.
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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

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
❤️Comfortable Family Home❤️
10.0 out of 10, Exceptional, (1)
"Good location near places, host was super friendly and very accommodating!"
❤️Comfortable Family Home❤️
Drury Inn & Suites St. Louis O'Fallon, IL
3.0 star property
9.6 out of 10, Exceptional, (1000)
"Very friendly nice front desk personnel. Great happy hour!"
The price is €112
per night
27 May - 28 May
Drury Inn & Suites St. Louis O'Fallon, IL
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.

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, apart-hotels, 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 favorite 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 depends 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 €184 per night. Entering your travel dates in the search wizard you might find 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.

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.

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