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, (47)
"It was a perfect space for us during my wedding weekend. The home was open and nice and easy to gather in "
Craftsman styled home in the heart of downtown Highland

The Swiss Post Apartment A

2.0 star property
The Swiss Post Apartment A

The Loft on the Square

10.0 out of 10, Exceptional, (1)
"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 B

2.0 star property
The Swiss Post Apartment B

3 Bedroom Loft overlooking water

9.6 out of 10, Exceptional, (105)
"15 minutes from gateway center in Collinsville, IL. Very nice neighborhood with a beautiful lake that is filled with fish, turtles, and ducks that our kids loved. We enjoyed the comfortable beds."
3 Bedroom Loft overlooking water

Historic Lebanon, quiet 2 Bedroom 2 Bath home!

10.0 out of 10, Exceptional, (37)
"Lovely place. The Christmas tree was special. "
Historic Lebanon, quiet 2 Bedroom 2 Bath home!

3 Bedroom Home - Lake Views on 3 Sides

9.4 out of 10, Exceptional, (91)
"The pictures match the property very well. House was clean stocked with everything that you would need for a family. There was good fishing on the lake."
3 Bedroom Home - Lake Views on 3 Sides

Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly

10.0 out of 10, Exceptional, (33)
"Great place to stay near McKendree Univ. Kitchen was better equipped than some house VRBO’a we have stayed in. Beautifully decorated and exactly as the pictures show. We will be back! Thank you for sharing your cottage with us. "
Everwood Cottage ^ Trees, Birds, and Quiet! Military Friendly

Private 4 Bedroom Home with a hot tub

9.4 out of 10, Exceptional, (50)
"Great house. Unique location in the country. Great access to St Louis and horse track in Collinsville, Illinois."
Private 4 Bedroom Home with a hot tub

The Hangar - Healthcare/Military friendly!

10.0 out of 10, Exceptional, (13)
"This place was awesome, very clean and had everything we needed, would definitely consider staying again!"
The Hangar - Healthcare/Military friendly!

THE NEST getaways&gatherings, beach/lake sleeps 20+

10.0 out of 10, Exceptional, (36)
"This is our second stay at the Nest. We love everything about it. House, Beach, Shade, Outdoor Play Area. The property managers are easy to reach and responsive. Highly recommend a stay here. "
THE NEST getaways&gatherings, beach/lake sleeps 20+

Cozy Corner Mascoutah

9.6 out of 10, Exceptional, (55)
"Perfect night for a quick in and out of town stay. There is a little bar within walking distance that my husband and son went to for a quick beer before bed. Hotels can be hard for a dog so this was exactly what we needed to keep our girl happy. "
The price is CA $151
CA $276 total
includes taxes & fees
Jan 16 - Jan 17
Cozy Corner Mascoutah

Downtown Midcentury Home- Walk to Everything!

10.0 out of 10, Exceptional, (21)
"Nice set up and spacious "
Downtown Midcentury Home- Walk to Everything!

The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock

10.0 out of 10, Exceptional, (19)
"We rented the Nest too. We had 8 people there and 11 at the Aerie. Each couple was able to have their own space this way. Adults didn't have to give up their privacy. At the Aerie, the living space, kitchen and rec room were spacious. We were fortunate to have perfect weather so we were outside all day and into the night. The outdoor space was fabulous for outdoor eating and "playing". We all give this venue A thumbs up!"
The Aerie- Luxury Lakeside Getaway - Private Beach & Boatdock

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

5 bedrooms near SAFB

7.0 out of 10, Good, (8)
"We loved our stay"
5 bedrooms near SAFB

Cozy Historic Downtown Edwardsville Charmer

10.0 out of 10, Exceptional, (4)
"Nice, comfortable, very clean home. Kurt was very responsive to our questions. Easy to get checked in. Nice to have quite a few basic supplies in the kitchen. Home is within a short walk to downtown Edwardsville. and restaurants close by."
Cozy Historic Downtown Edwardsville Charmer

Charming Edwardsville Home: Walk to Downtown!

10.0 out of 10, Exceptional, (11)
"What a cozy home. Christmas decor made it even more cheerful and inviting. Clean and roomy, Perfect location. We truly enjoyed our stay and definitely plan to be back. Thank you to our wonderful hosts."
Charming Edwardsville Home: Walk to Downtown!

Skyline - Military/Family Friendly

10.0 out of 10, Exceptional, (12)
"We had the greatest time! Never been to that area and we loved it! Your property was perfect in a perfect location!! We loved it! tMcKendree,Shiloh"
Skyline - Military/Family Friendly

The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB

10.0 out of 10, Exceptional, (2)
"Everything was as described in the listing. No issues during my stay! "
The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB
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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Other types of properties in Highland you may be interested in

Seasons Inn & Suites Highland

2.5 star property
8.2 out of 10, Very good, (542)
"Was in the middle of a renovation"
The price is CA $147
CA $164 total
includes taxes & fees
Jan 22 - Jan 23
Seasons Inn & Suites Highland

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (47)
"It was a perfect space for us during my wedding weekend. The home was open and nice and easy to gather in "
Craftsman styled home in the heart of downtown Highland

The Tibbetts House

3.0 star property
9.0 out of 10, Wonderful, (6)
"Owners were friendly, personable and helpful. We really enjoyed our stay"
The Tibbetts House
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.

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.