Highland Vacation Rentals

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Vacation Rentals in Highland

Craftsman styled home in the heart of downtown Highland
10.0 out of 10, Exceptional, (32)
"This house is perfect for a large group! We were extremely happy with the location to what we came to Highland for! Thank you again!"
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, (23)
"Very nice, very clean, and very “homey” place to stay. Excellent responsive host. 10/10 would stay again."
Historic Lebanon, quiet 2 Bedroom 2 Bath home!
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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
Cozy Corner Mascoutah
9.4 out of 10, Exceptional, (43)
"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 ¥16,509
per night
Jun 3 - Jun 4
Cozy Corner Mascoutah
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
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
Private 4 Bedroom Home with a hot tub
9.4 out of 10, Exceptional, (46)
"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, (4)
"We have stayed at this home before and like it."
Charming Edwardsville Home: Walk to Downtown!
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, (19)
"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)
"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
5 bedrooms near SAFB
9.0 out of 10, Wonderful, (4)
"We loved our stay"
5 bedrooms near SAFB
Cozy Historic Downtown Edwardsville Charmer
10.0 out of 10, Exceptional, (2)
"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)
"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
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
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)
"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
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
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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

Seasons Inn & Suites Highland
2.5 star property
8.4 out of 10, Very Good, (507)
"Breakfasts were goid. Room.was quiet. Housekeeping didnt bother us. "
The price is ¥16,163
per night
Jun 2 - Jun 3
Seasons Inn & Suites Highland
Craftsman styled home in the heart of downtown Highland
10.0 out of 10, Exceptional, (32)
"This house is perfect for a large group! We were extremely happy with the location to what we came to Highland for! Thank you again!"
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❤️
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.

Search for holiday rentals in Highland on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Highland?

Yes, we have vacation rentals near the most popular points of interest in Highland, or you can go with a secluded option if you want a relaxing place to stay. Our travelers 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's the top vacation rental that Highland has to offer?

Craftsman styled home in the heart of downtown Highland: This Highland vacation home rental is located in the city center and has a garden, a barbecue grill, 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 you can cook with friends or family.

How many vacation rentals are there in Highland?

Expedia has 3 vacation 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 larger area, you’ll find Korte Recreation Center and Copper Dock Winery.

What are vacation rentals like in Highland?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Highland. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family getaway.

Recent reviews of Highland properties
Expedia verified reviews